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Two-Week New England Road Trip Itinerary

A great loop through American history, high peaks, and picture-perfect countryside, this two-week New England road trip is a “grand tour” in every sense. The full itinerary means quite a bit of time on the road, so those looking for a more leisurely vacation should snip out bits of this route in exchange for extra beach days, hikes, and free time to explore along the way. But if you’ve got an itchy pedal foot and the urge to put in miles, this gives you the lay of the land and the very best of New England.

Days 1-2: Boston

Get a crash course in Revolutionary history on the Freedom Trail , which stretches from the shiny dome of the Massachusetts State House to the Bunker Hill Monument. Don’t tackle the whole thing at once—the trail isn’t complete without a lunch break in the Italian American North End neighborhood . Try Italian ice, cannoli, or a classic submarine sandwich before crossing the Charles River toward the USS Constitution .

On your second day, hop a ride on a swan boat in the Boston Public Garden . Then explore Back Bay’s art and architecture; duck into the sanctuary of Trinity Church, soak up the scholarly atmosphere in the Boston Public Library reading room, then stand in the center of the world at the stained glass Mapparium . Spend the afternoon in one of Boston’s fabulous museums, taking in ancient artifacts and contemporary art at the Museum of Fine Arts , or head to the Boston Tea Party Ships and Museum to reenact the city’s favorite piece of colonial-era sabotage.

Days 3-5: Coastal Maine and Acadia

270 miles, 5.25 hours.

Stop by Caffe Vittoria in the North End for an old-world cappuccino before picking up some wheels and heading to Portland , an easy, two-hour drive up the interstate. Before you reach the city, make a short detour to a trio of lighthouses in Cape Elizabeth . Portland Head Light is easily the most picturesque, but the pair of lighthouses known as Two Lights are a stone’s throw from classic lobster rolls at The Lobster Shack .

Get a taste of Portland’s maritime life on a boat tour of Casco Bay —hop a historic schooner or take a ride on the mail boat that connects the bay’s islands to the mainland—then kick off the evening by visiting some of the city’s award-winning microbreweries .

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On your second day on the coast, make an essential breakfast stop at Portland’s Holy Donut , then hit the road for a day of lighthouse-hopping and harbor-strolling. Drive up to Bath and work your way through the Maine Maritime Museum , or go a bit farther to Rockland and take in three generations of Wyeths at the Farnsworth Art Museum before visiting nearby Owls Head Light . Pick up a picnic lunch to eat near Rockport’s idyllic harbor, then visit the nautical boutiques in downtown Camden . Make the final push to Acadia National Park on Mount Desert Island, and turn in early if you’re planning to catch sunrise on Cadillac Mountain , a pilgrimage place where you can see the first sunlight hit the coast.

After your morning’s start, mountaintop sunrise or not, enjoy the rest of the day car-free in the national park; rent a bike, hop the free Island Explorer shuttle, and cruise the extensive network of carriage trails that link great stone bridges, viewpoints, and rolling mountains. For the real experience of a Maine lobster dinner, cross the island to Thurston’s Lobster Pound to get one with all the fixings at the edge of a scenic harbor.

Days 6-7: White Mountains

215 miles, 4.75 hours.

The route to the White Mountains crosses the dark, deep forests of inland Maine, ticking off a series of towns that recall the state’s immigrant heritage: Pass Naples, Sweden, and Denmark on your way to the outdoor mecca of North Conway . Stretch your legs after the long drive on the easy walk to Diana’s Baths , a series of small waterfalls perfect for an early evening dip (if there’s enough water). Fortify yourself for a day in the mountains with dinner and a locally brewed beer in town.

Day two is all about mountain peaks and rugged scenery: Chug to the top of Mount Washington on the 150-year-old cog railway, or hike the mountain yourself—on a clear day at the summit you’ll have views stretching from Maine to New York’s Adirondack Mountains, and you can watch a steady stream of Appalachian Trail through-hikers pose for photos at the top. For all of the mountain scenery and fewer crowds, opt for a trek up Franconia Ridge instead, choosing from a series of 4,000-foot peaks with views of the valley below.

Days 8-9: Southern Vermont

165 miles, 3 hours.

Take the Kancamagus Highway for a swooping, scenic drive through the mountains on your way to Woodstock , where you’ll find a classic village green, art galleries, and farm-to-table restaurants in a lush river valley. Hop a wagon ride, learn to churn your own butter, and get friendly with some Jersey cows at the Billings Farm & Museum , then spend the afternoon visiting classic covered bridges .

The drive from Woodstock to Brattleboro is another stunner, especially if you take the scenic route: Visit the President Calvin Coolidge State Historic Site to see his family homestead on your way to Route 100, then wind through pretty villages like Grafton. Spend an evening exploring Brattleboro’s art galleries, or catch a circus performance at the town’s New England Center for Circus Arts .

Day 10: The Berkshires

80 miles, 2 hours.

Watch the mountains taper into gentle hills as you make your way south, and choose a couple of the region’s best destinations for a classic Berkshires day: Spend the morning with cutting-edge modern art in North Adams at the MASS MoCA or follow in Thoreau’s footsteps to the top of Mount Greylock . After lunch, continue south to Lenox to visit the elegant home of Edith Wharton , then spend a quiet evening in the Brava wine bar, mingling with musicians from nearby Tanglewood.

Day 11: Newport

165 miles, 2.75 hours.

Keep pointing for the coast and you’ll wind up in this pretty port city, where the waterside Cliff Walk cuts past some of the grandest Gilded Age estates in New England. With just one day in town, pick a single mansion to explore before hitting the beach for clam rolls, sand, and sun. When the sun begins to slip, hop on scenic Ocean Drive to take in the coast with a stop at Castle Hill Inn for sundowners on The Lawn.

Days 12-13: Cape Cod

120 miles, 2.5 hours.

Drive all the way to “the end of the world”—that’s colorful, creative Provincetown to you—to spend your last days exploring Cape Cod. Make a beeline for the Cape Cod National Seashore when you arrive, where you’ll find the finest beaches in New England, crumbling cliffs, and historic lighthouses, and spend a day wandering the sand.

The next day, get a taste of Provincetown’s artistic heritage by strolling the downtown galleries , then join a tour of the rustic artists’ shacks scattered through the rolling dunes. See if you can keep up with the locals at a raucous tea dance, then spend a night on the town in true P-town style with tickets to a drag show.

Day 14: Boston

115 miles, 2.25 hours.

Start your last day of New England adventures with some pastries from the Portuguese Bakery , then hit the Cape Cod Rail Trail for a morning of exploring on two wheels. If you have time, break up the return drive to Boston with stops in one or more of the villages that line the Inner Cape: Visit Chatham ’s pretty lighthouse, play a round of pirate-themed minigolf in Yarmouth , or see a classic saltbox home in old-fashioned Sandwich .

Jen Rose Smith

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Moon New England Road Trip

by Miles Howard

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Moon Cape Cod, Martha's Vineyard & Nantucket

by Ray Bartlett

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The Flexible New England Road Trip Itinerary You Need in 2024 ❤️

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

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Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

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PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

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Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

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Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

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Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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• The Perfect New England Fall Road Trip for 2 Weeks

Looking to plan the perfect New England fall road trip and experience all those magical images you’ve seen online for yourself? Then you’re in the right place!

Fall is the best time to visit this region in the northeastern corner of the United States. Hiring a car and undertaking a road trip gives you the freedom to visit a variety of cities, towns, and nature areas.

As and when you like, you can pull over to take photos of the foliage and take yourself off for a hike among the beautiful nature.

But planning a New England fall foliage road trip itinerary takes a lot of time and thought. This is actually a very large area to cover and you need to plan it carefully to coincide with seeing the foliage at its peak. 

Two weeks is a great length of time for the road trip providing that you know how to maximize each day to its best.

That’s where this guide comes into the picture. This article is here to direct you to all the best fall drives in New England and help you organize the perfect adventure. 

* Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link. *

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Table of Contents

Useful Info for Planning Your New England Fall Road Trip

What is considered new england.

New England is the name given to a region in the northeast US. The region includes the six states of Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. This New England fall trip itinerary covers the first four states listed. 

Factors affecting peak fall foliage colors

First things first, let’s take a look at when peak fall foliage colors actually occur. A few conditions must be met in order for the leaves to change color and reach peak fall colors. 

First, the nights need to be cool but not freezing. The temperatures should be in the 40s °F (5-9 °C) range. If it gets too cold, the leaves will simply fall off the trees without changing color first.

Second, there needs to be plenty of sunlight during the day. If it’s cloudy all the time, the leaves won’t break down chlorophyll (green) as fast, thus the carotenoids (yellow and orange) will be only revealed later.

Third, there needs to be little or no wind. If the leaves are constantly rustling in the breeze, they will also fall off before changing color.

Finally, there needs to have been enough rain earlier in the season. The leaves need moisture in order to produce the vivid colors that we love so much.

Now that you know the science behind fall colors, let’s get into planning the perfect New England fall foliage road trip!

Best time to visit New England for leaf peeping

The best time to see peak fall foliage in New England is typically from the last week of September through the first two weeks of October. However, this can vary slightly depending on the year and the region. 

Generally speaking, the northernmost parts of New England will see the leaves change color first, and then it gradually rolls down into the southernmost parts. For example, you will see the leaves changing color in Upstate Vermont much sooner before you see them changing in Rhode Island.

Due to this, it’s practically impossible to experience the peak fall colors everywhere over the course of 2 weeks. Chances are that during these 2 weeks in New England you will either come across areas that are still a bit green, or that are already past their peak colors or even lost their leaves.

To get more specific information, it’s a good idea to check out the New England Fall Foliage Prediction Map .

This is updated regularly and shows where the foliage is currently at its best and where it is expected to peak in the coming week. I found that this map is pretty accurate but do keep in mind that conditions can always change and affect the timing.

My own 2-week New England fall road trip took place between 2-17 October in 2021. With this timing, Boston and Woodstock were both still a bit green but once we reached Stowe and continued onwards, we caught the peak colors everywhere else.

So if you can, you might want to consider aiming for a similar date range but do keep your eyes on the foliage predictions.

How to get to New England

Boston, Massachusetts, is the best place to start this particular New England fall foliage road trip itinerary.

Boston is served by Boston Logan International Airport (BOS) and is well-connected to other US airports as well as destinations further afield. You can fly directly to Boston from many European destinations. One in Boston, you can rent a car and hit the road. 

Once you arrive in Boston to start this fall road trip in New England, my tip is to compare car rental prices in Downtown Boston with those available at the airport. Sometimes they work out cheaper than renting at the airport.

This itinerary starts and ends in Boston so you will rent a vehicle and return it to the same place. 

However, if you have more time on your hands, you might also consider starting your trip in New York and heading northward from there. That way you can also explore the Big Apple! Remember to consult my travel guides to New York before you go. 

Where to stay during your New England fall road trip

As you can see, predicting when the peak fall colors will occur in advance is pretty difficult, which makes planning a bit harder. You don’t want to book your accommodation too far in advance because the leaves might not be at their best yet. But if you wait too long, all the good accommodation will be gone.

Generally, you have two options when it comes to planning your accommodation. Either you can book everything in advance and hope that you timed your trip right, or you can wing it and book things as you go.

The first option has the advantage of snagging up some good deals because the best places book out months in advance. It also gives you a bit more peace of mind knowing that everything is sorted.

The second option is a bit riskier but can also be more rewarding. It gives you the flexibility to change your plans on the fly and chase the fall colors wherever they might be.

If you do choose to wing it, my advice is to have a few accommodation options in mind for each night but don’t book anything until you know for sure that you will be staying there. That way, if everything is booked up you still have a Plan B and C to fall back on.

One more tip for booking your accommodation: If you run into issues finding a hotel in your desired town/city, I suggest looking further out. Change to a map view on the booking platform you use, set the filters to a 30-mile radius of each location, and you should find that you have better luck. 

Seeing as you will be traveling with your own rental car anyway, it shouldn’t interfere too much with this New England fall trip itinerary.

Another thing to keep in mind is that accommodation in New England can be quite expensive, especially in popular leaf-peeping towns. If you’re on a budget, I recommend staying in slightly less touristy towns and driving into the more popular ones for the day. This is what we did and it worked out great!

Another option is to stay at campgrounds. Camping is a great way to save money and it also gets you closer to nature. Just make sure to book your campsite in advance because they fill up quickly during peak season!

Recommended places to stay during your fall road trip

If you follow this New England fall road trip itinerary then I recommend staying in the following cities and towns:

• Boston: either 1 night or 2 nights depending on how your inbound flight works
• Woodstock VT: 2 nights
• Stowe VT: 3 nights
• Colebrook NH: 2 night
• Lincoln NH: 1 night
• Bar Harbor ME: 3 nights
• Salem MA: 1 night

As you progress through the itinerary you will see all my specific recommended hotels as per budget, mid-range, and luxury categories. 

Overview of Your New England Fall Foliage Road Trip Itinerary

Breakdown of your 2 weeks in new england.

Before we dive into all the juicy information, here is a quick overview of all the places you will visit during your New England fall road trip.

• Day 1: Boston (I recommend arriving on Day 0 so that you can settle and then look forward to spending an entire day in the city)
• Day 2: Drive from Boston to Woodstock, VT
• Day 3: Woodstock, VT
• Day 4: Woodstock, VT and drive to Stowe, VT
• Day 5-6: Stowe, VT
• Day 7: Hike the Mount Pisgah Trail North and drive to Colebrook, NH

Day 8: Dixville Notch

• Day 9: Franconia Notch
• Day 10: Scenic drive to Acadia NP via Kancamagus Highway and Conway 
• Day 11-12: Acadia National Park
• Day 13: Portland, Maine
• Day 14: Salem, MA and drive back to Boston 

Map for your New England fall road trip

Below you can find a customized map that includes all the locations you’re going to visit on this New England fall road trip itinerary. I marked the different parts of the road trip with different colors so you can easily see which places you’re going to visit each day.

If you open up this post on your phone and you click on the bracket in the upper right corner of the map, it will automatically save this map to your Google Maps app so you can always have it with you. Super convenient, right?

New England Fall Road Trip Itinerary for 2 Weeks

Now, let’s get into the finer details of your great adventure! This New England fall foliage road trip itinerary is broken down into each of the days and is packed with advice on what to see in each spot as well as tips on where to eat and where to stay.

This suggested itinerary starts and ends in Boston and all the drive distances and time estimates are included. 

Day 1: Boston

Welcome to Boston! Boston is one of the most popular cities for national and international tourists visiting the US. There’s lots to see and do but fortunately, you can get a decent overview with only one full day in Boston.

However, if you start your fall road trip in New England a day or two early then you can spend a little longer exploring the city. Alternatively, since your road trip will also end here, you can decide to add a few more days to the end as well.

As Boston is served by public transport and many of the main tourist attractions are within walking distance, you will not need to hire a car just yet. You can pick it up when you leave on day 2 of this itinerary.

Best things to do in Boston 

As a major city, there’s no shortage of things to do in Boston. You will need to do your research and decide how to spend your limited time in the city.

Below you can find some of the best things to do in Boston you can’t miss but if you prefer having a step-by-step itinerary, check out my guide on how to spend one day in Boston .

Walk the Freedom Trail

The Freedom Trail is the number one attraction in Boston.

This 2.5-mile (4 km) trail connects 16 of Boston’s historic landmarks that each relate to happenings from the American Revolution. Sites include Faneuil Hall, the Boston Massacre Site, the Old State House, the Benjamin Franklin Statue, and the King’s Chapel.

You can walk the Freedom Trail independently and enjoy checking out the buildings. The Freedom Trail website provides background information on each site.

Alternatively, you might rather join a guided tour if you want to hear all about the history from a local expert.

Subject to whether you complete the trail alone or join the tour, you should budget between 1-3 hours for this activity. 

Explore the North End

Boston’s North End is the oldest neighborhood in the city. It’s called ‘Little Italy’ due to the expansive Italian restaurants and bakeries. You will also see historic sites that include the 1680 Paul Revere House, Copp’s Hill Burying Ground, and the Old North Church.

The North End fits in nicely with your plans to walk the Freedom Trail as it contains some of the landmarks. Take the time to stroll around the area, through Langone Park, and along the waterfront.

Visit the Institute of Contemporary Art

The Institute of Contemporary Art is a must for artistically minded travelers!

Dedicated to all threads of visual arts, performance, film, video, and literature, the collection is vast and diverse. It will provide endless hours of chat for your New England fall foliage road trip once you leave the city behind. 

General admission is $20 and you are recommended to book tickets online in advance. The museum is open from 10 am-5 pm on Tuesdays, Wednesdays, Saturdays, and Sundays and 10 am – 9 pm on Thursdays and Fridays. It’s closed on Mondays. 

In case you need another reason to visit, this contemporary art venue offers exceptional views of the harbor.

Tour the Boston Tea Party Ships & Museum

This fascinating museum tour invites you to experience the political protest of 1773 against the British Parliament’s Tea Act. These events led to the American Revolution. 

The Boston Tea Party Ships & Museum tour is fully immersive and lets you relive battles and events with live actors, 3D holograms, and replica ships. At the start of the tour, you will receive a handbill from one of the colonists which will explain what part you’ll play. 

As the tour is popular, you will need to book ahead to secure your place. And, of course, there is a tearoom on site!

Where to eat in Boston

Boston has an exemplary food scene that’s blessed with a variety of international restaurants as well as local, regional, and national dishes. 

Seafood is BIG in Boston and if you like shellfish you should try at least one lobster roll during your New England fall road trip. These are like hot dogs but with lobster meat! Clam chowder is another specialty.

These are my recommendations for where to eat in Boston.

• Mike’s Pastry : Definitely swing by this North End bakery that specializes in the tastiest cannoli outside of Italy. It’s always busy so try to get there early. 
• Quincy Mar ket : This covered market contains boutiques as well as a vast array of food options. You can choose from Boston favorites or international food. It’s a top pick for lunch as well as sightseeing even if you eat elsewhere. 
• Saltie Girl : This chic restaurant in Back Bay focuses on raw dishes and seafood. Everything is artistically presented and sustainably minded. Plus, they have fabulous cocktails. 

Where to stay in Boston 

Because you are only spending a couple of nights in Boston, it’s best to stay in central accommodation. Actually, despite being a prominent city, Boston isn’t so large in comparison to other US cities. 

In terms of where to stay in Boston , Downtown Boston is always convenient and has the best selection of budget-friendly accommodation. If it’s your first time visiting or you are planning a shorter stay as per this itinerary then this is ideal. 

Back Bay, the North End, and the South End are all fantastic options for sightseeing, culture, and overall experience too. However, accommodation prices tend to be costlier. 

Here are my recommendations for where to stay in Boston.

LUXURY – The Eliot Suite Hotel

This luxury hotel located in the exciting Back Bay neighborhood is furnished with opulent rooms that have all the trimmings of a 5-star hotel. The sushi bar is a great shout if you fancy dining in one night.

MID-RANGE – Battery Wharf Hotel

Conveniently sited in the North End on the waterfront, some rooms at this mid-range hotel have harbor views. All units are spacious with desks and large windows while private bathrooms have either a shower or a bathtub. 

BUDGET – Moxy Boston Downtown

This budget-friendly hotel in Downtown Boston features themed rooms with stylish private bathrooms. Breakfast is a reasonable add-on and the hotel features reception staff around the clock.

Day 2: Drive from Boston to Woodstock VT

Driving time: 2 hours and 20 minutes (140 miles/225 km) direct from Downtown Boston or 5 hours and 15 minutes (237 miles/381 km) via the scenic route to Woodstock VT

You will need to check out your hotel today and make a decision about what to do with the second day of your New England fall road trip.

Option A, you can spend most of the day continuing to explore Boston and then drive directly to Woodstock in the afternoon or evening. 

Option B, you can turn the drive into a scenic road trip and visit a couple of sights. If you choose to stop off at all the places listed below, this will equate to 5 hours 15 minutes of driving time plus you’ll need to allow time at each place. 

In this case, I would recommend leaving your hotel as early as possible.

Madame Sherri Forest

Driving time: 2 hours 18 minutes (110 miles/177 km) from Boston

If you choose to take the scenic route to Woodstock VT, your first stop will be Madame Sherri Forest. This 513-acre plot of woodland once belonged to a notorious French-American socialite in the early 1900s.

Madame Antoinette Sherri was known for her eccentric parties that were attended by the rich and famous.

Unfortunately, her castle burned to the ground in 1962 but today you can still see the remnants of what once was. The arched stone staircase is the most iconic feature and makes for a great photo opportunity.

The forest is a great place for a short hike and it’s especially beautiful in the fall when the leaves start to change color. But even if not, it’s a beautiful introduction to New England’s natural scenery.

Once you’ve parked up you can follow the Wantastiquet Trail into the forest and see as much of the reserve as you have time for.

The full Wantastiquet Trail is 2.4 miles (3.7 km) and it’s easy and well-marked. You’ll pass through historic ruins and a lake, and enjoy vantage points over the forest. 

Southern Vermont Natural History Museum 

Driving time: 35 minutes (19 miles/31 km) from the Madame Sherri Forest 

The Southern Vermont Natural History Museum displays taxidermy of 250 species but it also has a sanctuary for injured birds under rehabilitation.

There is a modest admission charge of $5 to visit which goes directly towards the maintenance and care of the live animals.

There is an amazing foliage viewpoint right next to the sanctuary too that you can visit for free. This stretches out atop the Hogback Mountain Conservation Area and is a photographic addition to your New England fall road trip.

Driving time: 30 minutes (23.5 miles/38 km) from the Southern Vermont Natural History Museum

The small town of Bennington is one of the best places to visit in Vermont in the fall . It’s located in the southwest of the state and counts as one of the two shire towns. 

As you’re headed to Woodstock for the night, you won’t have too much time to explore. But you can wander along Main Street and grab a coffee and a snack or swing by the farmers market if your visit falls on a Saturday. 

You can also walk or drive to the Bennington Battle Monument with the option to take the elevator to the top and peer back at Massachusetts).

Hildene, The Lincoln Family Home

Driving time: 30 minutes (22 miles/35.5 km) from Bennington 

Hildene, The Lincoln Family Home is the former summer residence of Robert Todd Lincoln and his wife Mary Harlan Lincoln. It’s located a short drive out of Manchester and a fascinating attraction to include on your New England foliage road trip itinerary.

Robert and Mary oversaw the construction of this Georgian Revival mansion in 1905 and it served as the exclusive home to Lincoln’s descendants until 1975.

This handsome manor estate is open to the public for tours. You can tour the interiors of the building, the landscaped gardens, trails, goat dairy, and the greenhouse. 

Tickets may be purchased on the premises only; there is no option to pre-book your ticket in advance. Once you have a ticket you can roam at leisure but there are also options to take guided tours at select times. Admission is $23. 

Note that the grounds close at 4.30 pm so if you do want to visit Hildene, make sure you head there before exploring the town itself. 

Manchester 

Driving time: 5 minutes (1.7 miles/2.7 km) from Hildene 

Manchester is the other shire town alongside Bennington. Take a mooch along Main Street and don’t miss the picturesque white steeple church. 

There are a number of art destinations if time permits, such as the Southern Vermont Arts Center. If you time your New England foliage road trip right then this open-air sculpture gallery will look even more incredible than usual with its autumnal backdrop.

As with Bennington, Manchester has a reputation for great food so you could always eat dinner in town before completing the final leg of today’s drive. Main Street has an eclectic mix of taverns, upscale restaurants, and food trucks. 

Arriving in Woodstock

Driving time: 1 hour 20 minutes (57.3 miles/92.2 km) from Manchester to Woodstock

After a long day, it ’s time to settle in for your first night in Woodstock VT. Since you ’re looking at an almost 1.5-hour drive from Manchester to Woodstock, chances are it will be already dark outside when you arrive.

So settle in, grab dinner if you haven ’t already in Manchester, and have a good night ’s sleep!

Where to stay in Woodstock

Woodstock is a small town and it’s very popular during the fall season. Remember to book ahead to secure a hotel in the town center or plan to stay a little further out. As I mentioned before, I recommend booking 2 nights in this area.

In case Woodstock is fully booked out, you can take a look at accommodations in Quechee , Killington , or even Rutland .

Although Rutland is a 45-minute drive from Woodstock, this was the closest place where we found a room when booking our accommodation (we booked around 2-3 weeks before our trip).

We personally stayed at Days Inn by Wyndham Rutland/Killington Area , nothing fancy but it was perfect for a good night ’s sleep.

If you book well ahead of time and want to stay in Woodstock itself, take a look at these hotels depending on your budget.

LUXURY – Woodstock Inn & Resort

Located on the Village Green, this 5-star resort is convenient for the downtown sights and restaurants. The building exterior is practically palatial and sets the tone for what awaits you inside. Rooms are fitted with immaculate bathrooms while there is a garden to enjoy.  

MID-RANGE – 506 On the River Inn Woodstock

This central hotel comes with an indoor pool, sauna, gym, and restaurant. All rooms come with a balcony with options to reserve a river view. A daily buffet breakfast is included in the rate. 

BUDGET – The Birch Grove

This budget-friendly hotel provides a daily vegetarian continental breakfast. Rooms are homely and feature a seating area and excellent natural light. The hotel is located a short drive out of town and benefits from being surrounded by forest and mountain vistas.

Day 3: Woodstock

Spend the whole of your third day exploring Woodstock and the surrounding area. Woodstock is a photogenic town that is exquisite throughout the year but really shines during the fall season when the colors turn.

It’s the quintessential small rural town for your New England foliage road trip itinerary. There are countless amazing things to do in Woodstock VT , below you can see my top recommendations.

Explore Woodstock The Green 

Start your day with breakfast at Mon Vert Cafe on Central Street and witness how the town springs to life.

The breakfast menu is based on organic ingredients and you can choose from the likes of eggs, French toast, avocado on toast, and sandwiches.

Don ’t forget to wash it all down with a great cup of coffee! Mon Vert Cafe has a nice patio if it’s warm enough but there’s also space inside.

After breakfast, take a stroll along Central Street and The Green and note the historic buildings in this charming town.

Take a photo of Jenne Road Farm

Driving time: 15 minutes (8.5 miles/13.5 km) from Woodstock

Hop into your rental and drive 15 minutes south to Jenne Road Farm. This Instagrammable farm is privately owned but tourists are welcome to briefly stop to take a photo and perhaps make a purchase of their homemade maple syrup.

This is one of the best fall foliage drives in New England as you’ll see the scarlet-colored barns against the various shades of orange, red, and yellow.

Drive through the Taftsville Covered Bridge

Driving time: 20 minutes (12 miles/19 km) from Jenne Road Farm

The Taftsville Covered Bridge is just one of many historic covered bridges in Vermont . They were built during the 19th and 20th centuries to lessen the impact of flooding, provide shelter, and assist with the herding of livestock. 

The Taftsville Covered Bridge passes over the Ottauquechee River and was built in 1836. In fact, it’s one of the oldest bridges in the region. 

You can drive through the bridge but it’s also a good idea to park and wander down to the riverside to see the waterfall. 

The Taftsville Covered Bridge is a 20-minute drive from Jenne Road Farm. 

Explore the sights of Quechee 

Driving time: 5 minutes (3.5 miles/5.6 km) from Taftsville Covered Bridge to Quechee Covered Bridge, then 12 minutes (7.1 miles/11.5 km) from Quechee back to Woodstock

Quechee is a small village in Vermont where you can stop and have a stroll along Main Street. The Quechee Covered Bridge passes over the Ottauquechee River and marks the entrance to the town. 

This bridge is actually very young: it was only built in 1970 and renovated in 2012. It’s a wide, functional bridge with two lanes for traffic and a separate walkway for pedestrians.

Do park up and savor the experience of walking through and checking out views of the waterfall.

You can also pay a visit to the Quechee Gorge in the Quechee State Park. The gorge is known as the “Little” Grand Canyon of Vermont and I’m sure you’ll see how it earned that name!

The gorge was formed by glaciers during the last Ice Age and has a depth of 165 feet (50 meters). 

There is a fantastic viewing platform at the Quechee Gorge Bridge. Meanwhile, the Quechee Gorge Visitor’s Center is worth a trip during your New England fall road trip in order to understand the local history. 

Day 4: Woodstock and Drive to Stowe

This is your second day in the Woodstock area before relocating to Stowe for a couple of nights. You can check out of your hotel and visit the other places of interest near Woodstock before hitting the road for the short drive to Stowe. 

Sleepy Hollow Farm

Driving time: 7 minutes (2.8 miles/4.5 km) from Woodstock

Sleepy Hollow Farm is another private farmstead in the Woodstock area that is considered one of the best fall drives in New England. The red outhouses are set against a rich backdrop of Vermont hills and forestry. 

Although the farm is private and not open to the public, it is accepted that tourists can drive along Cloudland Road and stop to take a photo of the farm.

The drive from Woodstock takes 15 minutes, and be advised that it’s a very famous photo spot. You should aim to arrive early to avoid having to wait in a long line of cars!

2023 UPDATE: Unfortunately, access to Cloudland Road will be limited to locals only starting from 23 September to 15 October, so if you’re visiting during this period, you won’t be able to see the farm in person.

Sugarbush Farm

Driving time: 15 minutes (4.8 miles/7.7 km) from Sleepy Hollow Farm

Your second farm of the day is one for the foodies: Sugarbush Farm is responsible for some of the tastiest cheeses and maple syrup varieties in Vermont!

This 500-acre farm is owned by the Luce family and is open to the public. You can wander around the farm grounds, follow a designated nature walk in the forest, and pop your head into workshops.

This is great if you’re curious to see how the products are made. You will also learn about how maple syrup is sourced from the land.

There is no fee to visit Sugarbush Farm. However, it’s a kind gesture to make a purchase from the farm shop to support this family-owned business. 

Sugarbush Farm is located a 15-minute drive from Sleepy Hollow Farm.

Billings Farm & Museum

Driving time: 10 minutes (4.5 miles/7.2 km) from Sugarbush Farm

Billings Farm & Museum is located in central Woodstock. As well as being a working Jersey dairy farm, it has a great community ethos and hosts lots of events, and schedules educational programs with schools in the area.

There is an admission charge of $17 to enter and explore the barns, pastures, and kitchens. You can also take a look at the 1890s farm manager’s lodge and check out the collection of tractors.

You could choose to have lunch at the farm cafe or back in town before driving to Stowe. 

Arriving to Stowe

Driving time: 1 hour 15 minutes (72 miles/115 km) from Billings Farm to Stowe

After having lunch either at Billings Farm or in Woodstock, get back into your car and drive straight to Stowe. You ’re looking at a 1 hour 15-minute scenic drive.

Where to stay in Stowe 

You will need to book accommodation for 3 nights in Stowe, making this the longest temporary base during your New England fall foliage road trip. 

As you’re staying for 3 nights, you might prefer to stay in self-catered accommodation while in Stowe. There are so many grocers, independent stores, and farmers’ markets where you can stock up on groceries for a couple of nights.

One thing to note though is that accommodation in Stowe is quite limited and pretty pricy, especially during the fall season.

In case you want to book something further out, you should check out Waterbury (15-minute drive from Stowe), Montpelier (30-minute drive from Stowe), or Burlington (40-minute drive from Stowe). We personally stayed in Days Inn by Wyndham Colchester Burlington .

If your heart is set on staying in Stowe (which is a very good choice by the way!), here are my top picks for different budgets.

LUXURY – Trapp Family Lodge

Bringing a sense of Austria to your New England fall trip itinerary, rooms at the Trapp Family Lodge offer mountain views. The lodge is convenient for wine and beer drinkers – the Wine Cellar and von Trapp Brewing are located on the premises.

MID-RANGE – Sun & Ski Inn and Suites

Spacious rooms come with private bathrooms and a coffee maker. All guests have access to the indoor swimming pool, bowling alley, and mini golf course. Breakfast is included in the rate.

BUDGET – Timberholm Inn

This family-run bed and breakfast overlooks the Green Mountains and is 5 minutes by car to central Stowe. Rooms offer views of the gardens, mountains, or forest and there is a communal lounge with a fireplace and a vast supply of books. Breakfast is included in the rate.

Day 5-6: Stowe

If you loved Woodstock then you will love the next stop on your New England fall road trip as well!

Stowe is another small Vermont town with a cozy vibe and tons of remarkable nature sights and historic attractions. As there is so much to see and do in this area, it’s best to spend a whole two days exploring. 

Best things to do in Stowe 

As the area holds so many attractions, I wrote a complete guide about all the best things to do in Stowe which you can consult for the full experience.

Otherwise, here are some of the most popular things you can take your pick from and devise your own perfect 2-day itinerary.  

Explore Main Street

Stowe Main Street is the epicenter of the town. It’s lined with pretty historic townhouses and churches. There is also the Vermont Ski and Snowboard Museum and The Current art gallery if you want to squeeze in a culture dose.

Naturally, Main Street is humming with cafes and boutiques so if you want to pick up souvenirs or treat yourself to a long brunch: this is the place!

Drive through Smugglers ’ Notch

One of the best things to do in Stowe, Vermont is to take a drive through Smugglers’ Notch. This narrow passageway was once used by smugglers to transport their goods into the United States from Canada.

Nowadays it’s a popular scenic route and it’s especially beautiful in the fall when the leaves are changing color. The road winds its way through the mountains and there are plenty of pull-offs where you can stop and take in the view.

There are also a few hiking trails in the area if you want to stretch your legs. The Notch Visitor Center is a great place to start your exploration of Smugglers’ Notch and it has a range of maps and information about the area.

Visit the covered bridges

If you enjoyed seeing the covered bridges near Woodstock then you can continue your investigation while in Stowe.

There are several options that are nearby. In fact, the Giles W. Dewey Memorial Bridge is right in town so you needn’t use the car for this one! 

This bridge was only built in the early 21st century, in honor of a local farmer and philanthropist who passed away in 2000. Uniquely, the Giles W. Dewey Memorial Bridge only covers a pedestrian walkway rather than the road. 

The Gold Brook Covered Bridge passes over the namesake brook. But, it’s more commonly known as Emily’s Bridge. Emily was a young woman from a poor family who fell in love with a wealthy local man during the 1850s.

After he failed to show up and elope as the lovers planned, the woman leaped from this bridge and ended her life. Local fables suggest that her spirit haunts the bridge. 

Grist Mill Covered Bridge is also referred to as the Scott Covered Bridge, the Bryant Covered Bridge, and the Canyon Covered Bridge. It’s beautifully photogenic, especially during this time of year when the structure is devoured by the foliage. Passing through the bridge is one of the best fall drives in New England.

Chase a waterfall

If you love to chase waterfalls while traveling, then you have a couple of options to add to your list while in Stowe. 

One option is Sterling Gorge Falls which is a 15-minute drive north of Stowe. Access is via an easy out and back path through the Green Mountains that takes around 90 minutes to complete. 

A second is the Moss Glen Falls. These falls are only a 10-minute drive northeast of Stowe Main Street and this is actually the tallest waterfall in the state of Vermont. You can hike there in 20 minutes via one trail or take a scenic route that requires 2-3 hours. 

Walk the Stowe Recreation Path  

The Stowe Recreation Path is a 5.3-mile (8.5 km) walkway that links Stowe center with the Top Notch Resort on Mountain Road.

This entire walk is paved and is suitable for walkers and cyclists of varying levels. You don’t need to be an expert hiker and it’s a family-friendly activity. 

If you time your New England foliage road trip right then you will see the forest in its seasonal spectacle!

Take a hike

In addition to the Stowe Recreation Path, there are a number of excellent hiking options around the town if you want something more challenging.

Sunset Rock is an easy hike that takes less than an hour as a round trip. You will follow a steep but short trail through the woodland to a lookout point from where you will be able to view the town and Mount Mansfield. 

Smugglers’ Notch State Park offers a nice spread of short walks that take 1-2 hours to complete as well as challenging trails of 3 hours or 4-6 hours. 

Last but not least, the Sunset Ridge Trail is one of the most popular hikes if you want a closer look at Mount Mansfield. With a length of 5.1 miles (8.2 km) and somewhat challenging conditions, it is considered a moderate hike and will take up the majority of one day. You will need decent hiking boots as well. 

Savor the views from the Stowe Mountain Resort

Stowe Mountain Resort opens for winter sports in late November. But you can visit at any time of year to appreciate the views from the highest mountain peak in Stowe. 

You can drive up to Mountain Road which is one of the best fall foliage drives in New England.

Once you reach the resort, subject to the dates you visit, you can ride up the rest of the way to the summit of Mount Mansfield via the Gondola Skyride . This attraction typically opens from mid-June until mid-October. 

Once at the top, you will appreciate an unbeatable view of the golden foliage.

Where to eat in Stowe

Stowe’s Main Street is great for dining but as you have your car you can also check out places on the outskirts too. These are my suggestions for where to eat in Stowe. 

• Plate : This pretty restaurant presents a fusion of California-inspired recipes using seasonal Stowe-sourced ingredients. Dishes pair to perfection with their craft cocktail menu.
• Von Trapp Brewery & Bierhall : Visit this amazing brewery for Austrian-style brews and food that you can enjoy with a 360-degree view of the scenery.
• Green Goddess Cafe : Pick up an organic breakfast smoothie or a deluxe sandwich or salad for lunch and you’ll feel nourished from head to toe!
• Ben & Jerry’s : The factory for the iconic ice cream chain is located in Stowe. You can visit for a tour and pick up a new flavor while you’re there at the Scoop Shop. 

Day 7: Mount Pisgah Trail North and Drive to Colebrook

Today you will check out of your Stowe accommodation and drive towards Colebrook NH with the option to take a hike while on the way. 

Hike the Mount Pisgah Trail North 

Driving time: 1 hour 10 minutes (52 miles/84 km) from Stowe

The Mount Pisgah Trail North is a moderate hike of 4.8 miles (7.7 km). It has an elevation gain of 1,650 feet (503 meters) and takes approximately 3-4 hours to complete.

Parts of the trail are steep and it can be slippery after recent rainfall so dress sensibly and take care. 

Tackling this hike takes you into the Willoughby State Forest. You’ll follow a path that gradually reaches an observation clearing at the summit and provides a panoramic view of the lake.

Actually, you don ’t even need to go all the way up as there are a couple of viewpoints a bit lower as well that provide stunning views too.

The colors at this time of year are out of this world: the hike is a must for your fall foliage New England road trip if you love to hike!

You can leave your car on the side of the road on Route 5A next to Willoughby Lake and then follow the trail.

If you have a bit more time after your hike, it ’s worth exploring the lake too. The South Beach is especially stunning!

Drive to Colebrook NH

Driving time: 1 hour (44 miles/70 km) from Mount Pisgah

Once you’ve finished the hike you can just drive directly to Colebrook, New Hampshire, or feel free to stop off along the way.

Your drive will pass through the town of Brighton which sits on the banks of Island Pond and the Brighton State Park.

Check out Jesse’s Little Kitchen if you fancy a post-hike pizza binge or Hobo’s Cafe which offers a spread of brunches, grills, and comfort meals. 

Where to stay in Colebrook

Colebrook is a small town with a limited supply of accommodation options during your New England fall road trip. These are my picks for where to stay in Colebrook.

We personally managed to snag up a room at Colebrook C.C. & Motel and it was the perfect base to explore the Dixville Notch area.

If they ’re all booked out or you ’re looking for something else, check out my other recommendations below.

MID-RANGE – Mohawk Cottages

All units at Mohawk Cottages come with either one or two beds, a private bathroom, and a kitchenette. Pets are welcome and the location is perfect for getting into town and exploring the nearby sights.

BUDGET – Ladd Pond Cabins and Campground

This campsite offers a mix of self-contained cabins and lodges with basic kitchen facilities. The grounds are peaceful and give you the chance to soak up the sublime nature. You can even swim in the pond or borrow a kayak. 

You will spend today exploring the area around Colebrook and then return to the same hotel. Here is the itinerary for the day!

Breakfast at Mostly Muffins

Mostly Muffins is a breakfast-only cafe in the heart of Colebrook on Parsons Street. They open at 6 am on weekdays and 7 am on Saturdays (closed on Sundays) in case you want to wake up super early!

Muffins are available in a variety of flavors and you can grab one to go or eat in at the rustic cafe. They also serve amazing lattes – if you love sweet drinks, you have to try their maple latte!

If you would rather dine with a scenic view, ask for a takeaway and drive 5-minutes to Beaver Brook Falls. The scenery is absolutely mindblowing and there are lovely picnic tables where you can sit down and eat your breakfast while admiring the views.

Table Rock Hike

Driving time: 15 minutes (10 miles/16 km) from Colebrook

The Table Rock Hike is a short but moderately challenging hike in the Dixville Notch State Park. This 1.5 miles (2.4 km) out and back route has an elevation gain of 750 feet (229 meters) and takes around 1 hour to complete. 

The trail is easy to follow but it can be prone to mud and slippery leaves so you will need to wear hiking boots. Especially the last part is challenging but nothing you can ’t handle with some caution.

Once you reach the top, you will be rewarded with views stretching out over the dense foliage of the state park and Lake Gloriette.

One thing to note though is that you will be standing at the edge of a cliff with a huge drop so make sure to be extra careful.

It’s a truly phenomenal addition to your New England fall road trip itinerary but you’ll need a head for heights. If you have fear of heights, this hike might not be the best option for you.

The trailhead for the Table Rock Hike is located on NH-26.

Lake Gloriette

After completing the Table Rock hike, it ’s worth taking a stroll around the shores of Lake Gloriette as well. It ’s absolutely breathtaking with all the fall colors and if you are lucky and the conditions are great, you can even see some insane reflections on the surface of the water.

You might be wondering: what is the building across the lake that looks like a fairytale castle? That ’s The Balsams resort, a grandiose hotel and ski resort. Unfortunately, it has been closed ever since 2011 for development purposes and it will remain closed until further notice.

Huntington Falls

Driving time: 2 minutes (1 miles/1.6 km) from Table Rock Trailhead

Huntingdon Falls is a gorgeous waterfall located in the woodlands. Once you park up on NH-26 at the Dixville Notch Wayside parking area, you’ll see a smaller waterfall first. This one is visible from the parking lot.

But a short walk through the forest brings you to a second fall that tumbles down from the ravine. The walk is a mere 0.4 miles (0.6 km) and it’s easy and takes less than 20 minutes to reach the second waterfall. 

The waterfall is only a few minutes drive from the Table Rock Hike trailhead. 

Dinner at Black Bear Tavern

Driving time: 15 minutes (12 miles/19 km) back to Colebrook

Once you’re back in Colebrook, my recommendation for dinner is the Black Bear Tavern .

If the weather is comfortable, you can sit out on the terrace and enjoy a sundowner before eating. In addition to wines, beers, and spirits, the tavern has a great spread of signature cocktails. 

The food is high-quality American pub fare with the likes of burgers, grills, and shareable sides.  

In a nutshell, it’s exactly what you need in between a few days of hiking.

Day 9: Franconia Notch and drive to Lincoln

You will check out of your Colebrook accommodation this morning and head towards Lincoln NH with some scenic stops on the way in Franconia Notch State Park. 

Hike to Artist ’s Bluff 

Driving time: 1 hour 20 minutes (65 miles/105 km) from Colebrook

Artist’s Bluff is a 0.5-mile (0.8 km) loop trail that rewards you with magical views of Franconia Notch State Park from the lookout. It’s stunning year-round but particularly special when visited during a fall road trip in New England.

The trail is quite steep and can be a bit slippery but it’s super short – it took us a solid 10-minute to get to the top. Definitely one of the most rewarding hikes I ’ve ever done!

I recommend leaving the car in the Cannon Mountain Rv Park as this is the closest one to the trailhead. The start of the trail is on Profile Road, you will see a wooden sign pointing you in the right direction.

You will come across a fork during your climb – make sure to keep right and follow the sign to Artist Bluff! The other trail is going up to Bald Mountain which is an amazing hike as well but definitely longer.

Once you get to the top, you can enjoy the view of Echo Lake and the surrounding mountains. It was one of my favorite viewpoints during our New England fall road trip!

Flume Gorge 

Driving time: 10 minutes (6.5 miles/10.5 km) from Artist ’s Bluff

Flume Gorge is located just outside of Lincoln, New Hampshire and it’s one of the most popular attractions in the White Mountains region.

The Flume Gorge is a natural chasm that was created by glaciers centuries ago. The walls of the gorge rise to a height of 70 feet (21 m) in some places and it’s home to a number of waterfalls.

You can explore this stunning natural attraction by following a 2-mile (3.2 km) nature trail through the gorge. The walk is super easy and it’s suitable for all fitness levels.

The entire loop takes around 1.5 hours to complete and the park usually closes at 4 pm so you need to be mindful of your timing.

Online reservations cost $18 while buying on-site is $21. In the fall season, tickets sell out pretty quickly and typically they don’t accept walk-ins so it ’s best to arrive with a reservation.

Lincoln NH 

Driving time: 10 minutes (5 miles/8 km) from Flume Gorge

Another night, another cute New England town to call home! Once you’re ready, you can head to your hotel in Lincoln, NH. I recommend booking one night here because tomorrow you ’re going on another adventure!

Where to stay in Lincoln

These are my picks for where to stay in Lincoln NH with different budgets in mind.

LUXURY – RiverWalk Resort at Loon Mountain

Located in close proximity to Loon Mountain, RiverWalk Resort features a restaurant, a fitness center, and an outdoor pool. The one-bedroom suite can accommodate up to 8 people which is amazing for families or bigger groups.

MID-RANGE – Woodwards White Mountain Resort BW Signature Collection

Rooms at this recently renovated resort are equipped with a microwave, a refrigerator, and coffee-making facilities. Breakfast is included in the rate and the property features a swimming pool and spa. 

BUDGET – Riverbank Motel and Cabins

Located on the banks of the Pemigewasset River, this pleasant motel consists of simple yet comfortable studio rooms with basic kitchen facilities. Guests have access to an indoor/outdoor pool, hot tub, fitness center, tennis courts, and a games room.

Day 10: Scenic drive from Lincoln to Acadia National Park via Conway

Today will be all about road tripping, as you will drive all the way to Acadia National Park from Lincoln! You will drive through one of the most beloved mountain roads, Kancamagus Highways, where you can stop to see different attractions.

The whole driving time is 4.5 hours (245 miles/395 km) without any stops or traffic jams so essentially, you ’ll spend the whole day in transit. I recommend leaving as early as you can as the Kancamagus Highway is known for its insane traffic, especially during fall!

Breakfast at Flapjacks 

Today has many stops so head to Flapjacks on Main Street for a decent breakfast before you leave. They are legendary for pancakes (aka flapjacks, as they call them) with a good offering of sweet and savory variations that will power you up for the day ahead.

Flapjacks is really popular among locals and visitors as well so it ’s not uncommon to see lines in front of the restaurant. As I mentioned before, I suggest starting the day early! They usually open at 7 am.

Kancamagus Highway 

Driving time: 45 minutes (35 miles/56 km) to Conway from Lincoln via the Kancamagus Highway (excluding stops and traffic)

The Kancamagus Highway is one of the best fall drives in New England. It’s technically a 50-minute drive without stops from Lincoln to Conway but I would budget at least 3 hours so that you can stop at the amazing attractions as you pass through the White Mountains. 

I’ve written a complete guide about the Kancamagus Highway fall foliage drive with every possible information you could ever need to plan your drive. However, if you’re in a rush, you can check out the most famous attractions below.

Hancock Overlook

Hancock Overlook is a viewpoint that lets you take in the mountains towering above a blanket of autumnal foliage. It’s a quick stop but extremely worth stopping for if you catch the season just right. 

Sabbaday Falls

Pull over at the Sabbaday Falls Observation Site parking lot and from there it’s a very small hike to see this magical waterfall among the woodlands.

It takes around 15 minutes each way if you want to see the falls. 

Rocky Gorge Scenic Area

Stop at the Rocky Gorge parking lot then you can walk to this scenic lookout at the side of the Swift River.

You’ll see a waterfall coming down the side of the huge boulders and rocks with trees surrounding the area. Again, the walk only takes around 15 minutes each way.

Lower Falls

The Lower Falls is another pretty waterfall on the course of the Swift River. These are viewable after a short stroll from the Lower Falls parking lot on the Kancamagus Highway.

Albany Covered Bridge

One final covered bridge to star on your New England foliage road trip itinerary! This one passes over the Swift River toward the end of the Kancamagus Highway.

It was built in 1858 and renovated in 1970. There should be enough space to pull over and pop out to get a closer look and snap a few photos. 

Conway, New Hampshire

Conway is a small town located in eastern New Hampshire that marks the end of Kancamagus Highway.

This quaint town is the perfect place to stop for a bite to eat if you’re feeling hungry. One of the best-rated restaurants in Conway is Sweet Maple Cafe , which serves up amazing breakfast dishes, sandwiches, and salads. They do close at 2 pm so make sure you get there early!

Alternatively, you can stop at Fire 21 Pizza for a quick and tasty slice of pizza. This place is located right on Main Street and it’s the perfect spot to refuel after a day of exploring.

In terms of sightseeing, there are two covered bridges in Conway that are worth checking out: Swift River Covered Bridge and Saco River Covered Bridge.

Both bridges are located close to downtown and they’re easy to find. They’re also popular spots for photographers, so make sure you bring your camera!

Drive to Acadia National Park 

Driving time: 4 hours (211 miles/340 km) to Bar Harbor from Conway

After exploring Kancamagus Highway and stopping for a quick food break in Conway, you need to get back to your car as there is a long drive ahead of you.

The drive from Conway to Bar Harbor is a solid 4-hours which is one of the longest routes you ’ll have to tackle on this New England fall road trip.

Where to stay in Acadia National Park

Acadia National Park is located on an island that is connected to the mainland via road. You can stay in the park at one of the designated campgrounds if you want an immersive nature experience. Alternatively, there are hotels and guesthouses dotted around the island.

However, the best place to stay for the course of your visit is Bar Harbor. This is the main town within Acadia NP and has the widest variety of accommodation options as well as restaurants, shops, and amenities.

As you will likely stay for two nights, you can either stay at the same hotel for both nights of your fall road trip in New England. Or, you could stay at two different places and experience different parts of the park.

Your third option is to only stay one night at Acadia NP and then drive to Portland after your second day on the island. You can then stay the night in Portland.

If you want to know more about the best areas to stay in Acadia, check out my in-depth article about where to stay in Acadia .

You can check out the full list of the best hotels in Acadia National Park for every budget , or if you’re in a rush, take a look at my top picks below.

LUXURY – Bar Harbor Inn and Spa

Located on Mount Desert Island, this Bar Harbor hotel is only 6 miles away from the Jordan Pond in Acadia National Park. The oceanfront hotel offers an on-site restaurant and guests can dine with views of the ocean.

MID-RANGE – Saltair Inn Waterfront B&B

This evocative guesthouse grants access to a private beach area and a terrace. Rooms are lavishly appointed with some coming with clawfoot bathtubs. An American breakfast is included in the rate.

BUDGET – Bar Harbor Manor

This clean and comfortable property is conveniently located in Bar Harbor. Rooms are homely and generously proportioned. Staff are extremely hospitable and will be able to provide any pointers on exploring the national park.

Days 11-12: Acadia National Park

Acadia National Park is located on Mount Desert Island and comprises 47,000 acres of coniferous forest, rocky beaches, and glacier-carved granite peaks.

You will note Cadillac Mountain – the highest point on the East Coast. 

As you have a car already, you can explore the park with your own vehicle. But, if you fancy taking a break from driving, you could always consider using the bus. 

The Island Explorer is a complimentary bus service that departs from Bar Harbor and links with the tourist spots and hiking trails within the park.

In addition to being free, the bus means that you will not encounter parking issues. Spaces are limited in Acadia, and since it ’s one of the most popular East Coast National Parks , sometimes it’s impossible to score a spot.

Particularly at this time of year because the Park Loop Road easily constitutes one of the best fall foliage drives in New England.

Read Next: Acadia National Park in the Fall: Practical Info & Tips for Visiting

Best things to do in Acadia National Park

Once you’ve decided how you’re going to get around, here are the best things to do in Acadia. In case you prefer a step-by-step itinerary, you can refer to my in-depth guide on how to spend 2 days in Acadia National Park .

Walk (or drive) Ocean Path

Ocean Path is a scenic route that connects Sand Beach with Otter Point. 

The trail is 2 miles (3.2 km) and an easy, flat walk. On the way, you will encounter Thunder Hole – a chasm where waves crash and create the sound of thunder. You should expect to complete the out-and-back trail in less than 2 hours.

If you would rather save time for other hikes, you can drive Ocean Path in your vehicle and enjoy the ocean views along the way.

Hike to the Beehive Lookout 

Naturally, there are dozens of hiking trails in Acadia NP that you can enjoy during the two days of your New England fall foliage road trip. 

The Beehive Lookout is one of the best places for views in the entire park. However, you should note that the Beehive Trail is an extremely challenging hike that is intended only for advanced hikers with climbing experience and no issues with heights. It requires you to shimmy along a vertical cliff.

However, you can decide to follow the Bowl Trail instead, which departs from the same trailhead as the Beehive Trail. If you take a shortcut through the forest, you will end up at the Beehive Lookout without having to do the hard climb!

Follow the Jordan Pond Path

If you have time for another hike, the Jordan Pond Path is a lovely choice. At 3.1 miles (5 km) and with flat terrain, the hike can be completed in 1-1.5 hours and is not challenging. 

If you want to extend the hike then you can merge this route with another hike: the Bubbles Trail. The Bubbles is the name given to the two mountains, North Bubble and South Bubble. You’ll spot them as you walk around the lake but summiting them yields an incredible 360-degree view of the area. 

This results in a moderate 7.4 km (4.6 miles) loop hike beginning and culminating at the Jordan Pond Path trailhead. This option does have some pretty steep sections as you venture up through the forest but it’s worth it for the views.

Catch the sunset at Cadillac Mountain 

Cadillac Mountain is 1,530 feet (466 meters) tall and is the highest peak on the East Coast of the US. You can drive to the summit via Cadillac Summit Road and see incredible views over Jordan Pond and the surrounding ranges.

However, you must reserve your drive in advance. This is to prevent overcrowding and carries a small conservation fee of $6 per vehicle. 

30% of the allocated spaces are bookable 90 days ahead of the date. Meanwhile, the remaining 70% are released at 10 am two days ahead of your intended date. You’ll need to be super organized in advance or super crafty at the last minute!

Sunrise and sunset are the most popular times but it’s usually easier to secure a reservation for Golden Hour.

Take a boat tour 

A boat tour is a perfect way to see some wildlife during your New England fall road trip.

Tours depart until late October from Bar Harbor and you will stand a chance of spotting eagles, porpoises, seals, whales, and other marine creatures. 

The 2-hour Sightseeing & Nature Cruise with Acadian Boat Tours is one of the most comprehensive options. On the other hand, the 3.5-hour variation takes you to see the puffins which is always going to be a win!

Where to eat in Acadia

Hiking requires a solid base of energy! Here are my recommendations for where to eat in Acadia NP. 

• Cafe This Way : This Bar Harbor cafe opens bright and early at 6.30 am and is a great spot for breakfast before road tripping around the national park. Eggs, pancakes, French toast, and organic granola will keep you full all day. 
• 2 Cats Bar Harbor : Another amazing breakfast place to fuel up for the day! They prepare bagels, French toast, pancakes, and nutritious homemade granola alongside bottomless coffee and freshly squeezed juices.
• Atlantic Brewing Midtown : Sample locally brewed beer with a hot dog or pretzel at this funky brewery. There’s a terrace which is perfect for catching the last of the sunshine. 
• Jordan Pond House : This attractive restaurant offers views of Jordan Pond and the mountains. Order catch of the day and don’t miss their popovers. 
• Side Street Cafe : This ambient eatery focuses on burgers, clam chowder, and lobster-based dishes. 

Day 13: Portland 

Driving time: 3 hours (175 miles/282 km) from Bar Harbor to Portland

Today you will be visiting one of the prettiest places along the East Coast: Portland, Maine!

Portland is the most populous city in Maine and it’s a worthy addition to your New England fall road trip. This historic city is located on a peninsula and it’s known for its working waterfront, as well as its beautiful lighthouses.

Spending one day in Portland Maine will give you the chance to visit the highlights, however, since it ’s quite far away from Bar Harbor and you still have to drive to Salem afterward, this might feel like too much driving/not enough time to explore the city.

Therefore, an alternative option is to drive to Portland from Acadia NP the previous evening and spend the night there. You can take a look and see which option you prefer and customize the fall foliage New England road trip as you see fit. 

Best things to do in Portland

Portland, Maine is known for its historic downtown area and its influx of lighthouses, many of which remain in use. Here are the best things to do when spending one day in Portland. 

Wander around the Old Port

Old Port is Portland’s historic district and features cobblestone streets and beautifully preserved buildings. The waterfront bustles with restaurants, cafes, fish markets, and shops.

This is a great place to stretch your legs after the long drive from today’s leg of the New England fall road trip while tucking into a lobster roll. 

Visit the Portland Observatory

The Portland Observatory was built in 1807 and originally served as a communication station for the port. It is the only wooden signal towel that still exists in the area. 

After various renovation work during the 20th century and the turn of the 21st century, the Observatory was added to the National Register of Historic Places.

You can go inside the observatory during the summer season until mid-October. Guided tours run on Thursdays, Fridays, Saturdays, Sundays, and Mondays while Tuesdays and Wednesdays switch to self-guided tours. 

You can book your tickets online in advance; admission is $10. 

Tick off the prettiest lighthouses in Portland

As a testament to the importance of Portland Harbor during the 18th and 19th centuries, you can find many beautiful lighthouses in Portland .

With one day in the city, you can check out a couple of them during your New England foliage road trip. If so, expect this to take up most of the afternoon. 

Bug Light sits across the bay from the Old Port in Bug Light Park. Officially it’s called the Portland Breakwater Lighthouse but it earned its nickname due to how petite it is. 

Spring Point Ledge Lighthouse is a short drive from Bug Light and you can visit it in conjunction with Fort Preble. This lighthouse sits on a rocky promenade and you can walk out to the end to get a closer look at the building.  

Portland Head Light is the most iconic of the famous Maine lighthouses. It’s located in Fort Williams Park, Cape Elizabeth – 5 miles (8 km) south of Downtown Portland. You can drive there in 15 minutes from the town center and then continue with your drive south to Salem. 

Look across the bay and you might be able to spot Ram Island Ledge Light Station!

Where to eat in Portland

Portland is a great place to sample local seafood and shellfish specialties. But if you’re not keen on fish, there are plenty of other options.

These are my recommendations for where to eat in Portland for lunch or before heading to your hotel in Salem.

• DiMillo’s on the Water : This nautical-themed restaurant offers harbor and ocean views and a menu that celebrates the best seafood and shellfish dishes that Portland is known for. 
• Flatbread Company : For those who aren’t a fan of seafood, turn your attention to this waterside pizzeria. Pizzas are prepared with a wood burner and use organic ingredients and homemade sauces. There are plenty of options for gluten and dairy-free diners. 
• Central Provisions : Lip-smacking small plates, awesome cocktails, and an unbeatable atmosphere! Menus change seasonally and produce is locally sourced.
• Holy Donut : If you’re not that hungry or you’re looking for something sweet, check out Holy Donut. These legendary donuts are made using a potato base and come in a variety of innovative flavors including maple bacon, dark chocolate sea salt, honey lavender, and even cannoli.

Drive to Salem, Massachusetts

Driving time: 1 hour 30 minutes (97 miles/156 km) from Portland to Salem

After spending the day (or at least a couple of hours) in Portland, get back to your car and drive 1.5 hours to your final stop on this New England itinerary: Salem, MA.

Where to stay in Salem

A final reminder about how quickly accommodation in New England gets booked up in the fall season. Of all the places, Salem is one of the busiest especially as you inch closer to Halloween when the town has heaps going on.

Salem offers a wonderful mix of historic hotels and cozy inns that are right in the town center. These are my top picks for where to stay in Salem.

LUXURY – Northey Street House

This historic hotel consists of sublime rooms and a garden for guests to enjoy. It’s located within walking distance of downtown and includes breakfast in the rate. There is a small kitchenette for guests to share.

MID-RANGE – The Merchant

Uniquely decorated with a nod to the heritage of the town and building, this central hotel will appeal to those who appreciate old-worldly charms with a modern twist. Breakfast is included in your stay.

BUDGET – Hawthorne Hotel

Said to be one of the most haunted hotels in town, there’s no spookier place to stay in Salem Massachusetts in the fall! Period features and a characterful dining room with an open fire make this the perfect home away from home.

Day 14: Salem

It’s the last day of your fall foliage New England road trip! You’ll spend the day in Salem before heading back to Boston to complete the itinerary. Unless you want to spend a few extra nights in Salem!

Everyone’s heard of Salem and knows roughly about the history of the Salem Witch Trials. However, until you visit the town for yourself, it’s impossible to truly grasp the extent of the events that occurred in 1692.

These events are traced back to January 1692 when both the daughter and niece of Puritan Reverend Samuel Parris of Salem Village were taken ill. William Griggs, the village doctor, diagnosed the young women with bewitchment.

Thus, the trials began with accusations being cast at the women and men of Salem. 19 of the accused lost their lives to hanging while one man was pressed to death and countless other victims died in prison.

Modern-day Salem is a charming small town that recounts the events and honors those who lost their lives to the hysteria with the Salem Witch Trials Memorial.

Best things to do in Salem

There are lots of spooky things to do in Salem in the fall season. But, there is also a large choice of historic and outdoor attractions as well. Here are the best things to do in Salem.

See what’s on at Salem Haunted Happenings 

Salem Haunted Happenings is an annual celebration of Halloween and fall that has taken place since 1982.

The program runs across the whole month of October and has events like parades, spooky movie screenings, costume balls, performances, and bespoke ghost tours.

You can find out what’s on this year by consulting the Haunted Happenings website or by downloading the free app.

Visit the Hocus Pocus filming locations

The family Halloween movie of 1993 starring Bette Midler and Sarah Jessica Parker was set and filmed in Salem. You can visit a number of Hocus Pocus filming locations while in town either independently or as part of a guided tour.

The Salem “Hocus Pocus” Movie Locations Walking Tour only occurs during the fall season. So, seeing as you’re planning a New England fall trip itinerary, you can seize the opportunity. 

Check out the Peabody Essex Museum

For an entirely different change of pace, visit the Peabody Essex Museum (PEM). This gallery explores American and Asian art, architecture, and design and places an emphasis on cultural understanding and the importance of innovation.

You can visit the permanent collection and check what the latest special exhibition is. 

Besides the vast art on display, PEM features a garden and a cafe space in a beautiful modern atrium that’s filled with light. Admission to PEM is $20.

Tour witchy museums

It goes without saying that most of the attractions in Salem are witch-themed. Choose to visit the Witch Dungeon Museum where actors will walk you through the happenings of the 1692 Salem Witch Trials before inviting you to explore the dungeon artifacts. 

Meanwhile, the Salem Witch Museum is a sculpture exhibit with a voiceover of the events as well as an exploration of modern-day witchcraft.

The Witch House at Salem served as the home of Judge Jonathan Corwin who presided over the Salem Witch Trial. Built in 1675, the house hosted some of the preliminary questionings.

Nowadays it contains objects and artifacts from the time of the Witch Trials and gives you a sense of how the wealthy lived during the 17th century. 

If you’re traveling with kids for this New England fall road trip, then do check out the Halloween Museum of Salem .

Where to eat in Salem

Downtown Salem offers a mix of quirky cafes, global eats, and friendly taverns with comforting American fare. Here are my suggestions for where to eat in Salem.

• Bella Verona : This cozy trattoria whips up authentic Italian fare that will convince you that you’re in the Tuscan hills. Save space for dessert – their homemade cannoli are top-notch. 
• Wolf Next Door Coffee : This cute cafe specializes in breakfast sandwiches and muffins, pies, baked goods, and excellent coffee. They cater well to vegans and vegetarians.
• Mercy Tavern : A laid-back gastropub that focuses on New England comfort food and international favorites. Menus change frequently but you can expect the likes of burgers, mac ‘n’ cheese, and fish tacos. 

Drive back to Boston

Driving time: 30 minutes (22 miles/35.4 km) to Boston 

After touring all the spooky places in Salem, all that ’ s left to do from your New England fall road trip itinerary is to drive back to Boston and return your rental.

In case you have some more time on your hands, it ’s worth sticking around for a couple more days in Boston but even if you don ’t, I think you had an action-filled road trip that you will remember for a long time!

Planning a trip to New England?

Then you might want to take a look at all our other travel guides about New England. I promise, they are just as awesome as this article was!

• Vermont in the Fall: Travel Tips & Best Places to Visit
• 16 Incredible Things to Do in Woodstock VT
• 17 Amazing Things to Do in Stowe, Vermont
• 17 Incredible Covered Bridges in Vermont You Need to Visit
• 81 Amazing Vermont Quotes & Captions for Instagram

New Hampshire:

• Kancamagus Highway Fall Foliage Drive: 9 Best Attractions & Tips for Visiting

Massachusetts:

• How to Spend One Day in Boston: Itinerary & Best Things to Do
• 13 Best Day Trips from Boston You Can’t Miss
• Where to Stay in Boston: 8 Best Areas & Hotels
• 133 Best Boston Captions for Instagram (Quotes, Puns & More)
• 19 Spooky Things to Do in Salem MA in October
• How to Spend One Day in Acadia National Park
• The Perfect 2 Days in Acadia National Park Itinerary
• Acadia National Park in the Fall: Practical Info & Tips for Visiting
• How to Spend One Day in Portland, Maine
• 5 Prettiest Lighthouses in Portland Maine You Can’t Miss

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Two Week New England Road Trip Itinerary: Massachusetts, Rhode Island, Connecticut

This 14-day New England road trip through Massachusetts, Rhode Island, and Connecticut is full of American history. Learn about the Revolutionary War, experience the life of the Pilgrims, the 1692 Salem Witch Trials, and the wealth of the Gilded Age. You will also visit America’s favorite beach town and have the opportunity to take a ride across Cape Cod’s sand dunes before relaxing on an island (or two). Do not miss the once-in-a-lifetime experience to be kissed by a Beluga Whale at the Mystic Aquarium!

You are excited to begin your road trip through New England and want to know the best time of year to visit, where to stay, must-see attractions, and what to eat while there. Researching the best things to do on a road trip through New England while working full time is overwhelming and you don’t have hours to spend on the internet. Save time and plan an unforgettable trip full of top activities with this ultimate New England road trip itinerary through Massachusetts, Rhode Island, and Connecticut.

Read 10 Day Road Trip Through Maine, New Hampshire, and Vermont

New England Road Trip Planner

When is the best time to visit new england.

New England experiences all four seasons. The best time to visit New England for great weather and fewer crowds is in the spring (May to June) or fall (September to October). Spring temperatures range from highs in the 50s to 70s degrees F and the blooming of cherry blossoms. Summer temperatures range in the 80s, so this is a perfect time to visit the beach. However, it is the high season so book early and expect high prices. Fall temperatures from mid-September to early October are often in the 70s. Fall brings the changing of the leaves mid to late October. Winter is cold. Expect December, January, and February high temperatures of 37- 42 and low temperatures in the 20s. Snow is possible from November through April; January is typically the snowiest month of the year. The Boston Marathon, St Patrick’s Day, and Independence Day are popular times to visit Boston. Halloween is a very popular time to visit Salem and the islands and beach cities are busy during the summer months.

What is the Best Way to Travel in New England?

This New England itinerary utilizes planes, trains, buses, ferries, and a rental car. Save precious PTO by flying from your home to Boston Massachusetts. Use the Metro to explore the sights in Boston. Take a day trip to Salem Massachusetts by train, Salem is a walkable city. Then jump on a ferry from Boston to Provincetown, Provincetown is also a walkable city. You will then ride a bus to cross the Cape Cod National Seashore to catch ferries to Nantucket and Martha’s Vineyard returning to Woods Hole. In Woods Hole, you will rent a car for the remainder of the trip. Return the rental car to Boston Logan International Airport and fly home from Boston. This trip requires a lot of planning, but don’t worry, the specific of each step is described below.

How Long Do You Need to See New England?

The New England region is located in the Northeastern section of the US. It includes the states of Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. This itinerary is a fast-paced 14 days in Massachusetts, Rhode Island, and Connecticut. If you have more PTO, begin in Portland Maine. Spend 10 days exploring Maine, New Hampshire, and Vermont . Instead of departing in Portland, drive South and reverse the following itinerary.

How Expensive is New England?

According to Budget Your Trip , the average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

What to Pack for a New England Road Trip

New England experiences all four seasons. In the winter pack sweaters, a heavy coat, gloves, and a scarf. Expect snow; bring heavy socks and winter boots. Rain is common in the Spring, be sure to pack an umbrella and jacket. Summer is great weather to visit the beach, be sure to bring a bathing suit. Thunderstorms may occur in the summer, bring an umbrella to be prepared. Late Fall is “sweater weather” and a jacket is needed in the evening.

New England Road Trip Highlights

Boston Massachusetts | Freedom Trial | Boston Tea Party | Beacon Hill | Salem Massachusetts Witch Trials | House of Seven Gables | Cape Cod | Provincetown Massachusetts | US National Seashore | Nantucket Massachusetts | Martha’s Vineyard Massachusetts | Providence Rhode Island | Newport Rhode Island | Gilded Age Mansions | Mystic Connecticut | Mystic Aquarium | Plymouth Massachusetts | Plymouth Rock | Plimoth Plantation

Day by Day Guide for a Road Trip to New England (14 days, 13 nights)

ROUTE AT A GLANCE: Boston Massachusetts – Salem Massachusetts – Provincetown Massachusetts – Nantucket Massachusetts – Martha’s Vineyard Massachusetts – Providence Rhode Island – Newport Rhode Island – Mystic Connecticut – Plymouth Massachusetts – Boston Massachusetts HOW MANY DAYS: 14 days

Day 1, 2, and 3: Arrive in Boston Massachusetts

Boston is an amazing city full of American history. In fact, there are 58 National Historic Landmarks and almost 300 historic sites. In addition, you will find public gardens, brownstones, brick sidewalks, gas lamps, food halls, and breweries . Spend the next two days exploring the city and eating all the amazing foods Boston is known for: Boston baked beans, Boston chowder, Boston cream pie, lobster rolls, fried clams, and apple cider donuts. Be sure to walk the Freedom Trail and visit the Boston Tea Party Museum.

Fly into Boston Logan International Airport. The Silver Line provides free bus transportation into the city, and there are marked stops directly outside of each airport terminal. Yotel is a good mid-range hotel option in the Seaport Area. The hotel is 10 steps from the courthouse stop on the Silver Line and close to attractions, restaurants, and Cisco Brewers. Be sure to enjoy a seafood dinner at the Union Oyster House, America’s oldest restaurant.

Read Things to Do in Boston Massachusetts

Day 4: Salem Massachusetts

Salem is famous for the 1692 Salem Witch Trials. Ride the Salem trolley for a city overview, follow the Salem Heritage Trail, visit the House of Seven Gables or the Mayflower ship, tour the Witch House, attend a witch trial reenactment, have your palm read, attend a séance or learn to cast spells. Start the day early, there are so many things to do in Salem it is hard to decide how to spend your one day !

Head to Boston’s North Station and take the 30 min train ride to Salem on the Newburyport/Rockport Line.  Salem is a walkable city. It is a 10-minute walk on Washington Street from the Salem Train Depot to the attractions on Essex Street.

Read One Day in Salem Massachusetts

Day 5: Provincetown Massachusetts

Provincetown sits at the northernmost tip of Cape Cod on the U.S. National Seashore. The city has been called America’s favorite beach town. You will find the Pilgrim Monument, US National Seashore, sand dunes, dune shacks, lighthouses, beaches, shopping, cabaret, lobster rolls, and fried clams. Be sure to take a dune tour of the Cape Cod National Seashore and dune shacks. Provincetown Massachusetts is a fun destination, don’t miss my one-day itinerary to use your time wisely!

Check out of the Boston hotel and take the 9 am Boston Harbor Cruise direct ferry from Boston to Provincetown Massachusetts. Grab a coffee and a muffin before arriving at 66 Long Wharf early for an 8 am check-in. The ferry ride is 1.5 hours and docks at MacMillan Pier in the heart of Provincetown at 10:30 am. Be sure to photograph the Boston skyline while the ferry departs and the Long Point Light Station as approaching MacMillan Pier. Tip: Book the 11 am sand dune tour with Art’s. It is a 5-minute walk from the ferry and they will store your suitcase for you.

Read  Day Trip to Provincetown Massachusetts

Day 6: Nantucket Massachusetts

Nantucket is an island in Massachusetts full of history and listed as a National Historic Landmark. Nantucket is the perfect Cape Cod Island to rejuvenate and have a little fun. You will find crushed shell walkways, cobblestoned streets, bicycles with wicker baskets, a bluff walk full of shaker homes covered in roses, tall seagrass beaches, a wharf full of yachts, Main Street boutiques, and more. You only have one day in Nantucket , plan it well!

Check out of the Provincetown hotel and take the Plymouth and Brockton bus from behind the Chamber of Commerce on the Macmillian Pier to the Hyannis Transportation Center. The bus leaves at 6:30 am and arrives at the center at 8 am. Jump on the shuttle to the HyLine Ferry to Nantucket. Arrive at the ferry at 8:45 for a 9:30 departure, and grab another cup of coffee and a snack. Arrive in Nantucket at 10:30 and check into your hotel or bed and breakfast.

Read Nantucket Day Trip Itinerary

Day 7 and 8: Martha’s Vineyard Massachusetts

Martha’s Vineyard is an island in Massachusetts best known as the filming location for the movie Jaws. This island is the perfect Cape Cod spot to relax. You will find beaches, gingerbread cottages, old Captain Homes, Alpacas, lobster ice cream, lighthouses, copper lanterns, fishing boats, and, of course, Jaws (at least the famous bridge).

Check out of the Nantucket accommodation and walk to Straight Wharf for a 9:30 arrival. Take the Hyline Ferry to Martha’s Vineyard Oak Bluffs departing at 10:30 and arriving at 11:40. Check into the hotel and head to Circuit Avenue for lunch (and lobster ice cream) before checking out the Gingerbread Houses. On the second day, purchase an all-day bus pass to visit Edgartown, the Big Bridge made famous in Jaws, and see the alpacas.

Read Martha’s Vineyard Day Trip Itinerary

Day 9: Providence Rhode Island

Providence Rhode Island is full of history and worth a quick overnight stop. You will find the country’s first indoor shopping mall, First Baptist Church, colonial houses, a canal walk, gondola rides, the Superman building, street art, and coffee milk. Be sure to attend the WaterFire Celebration.

Check out of your Martha’s Vineyard hotel and walk back to the Oak Bluffs terminal for a 7 am arrival. No reservation is required, go straight to the terminal and purchase your ticket to Woods Hole. Depart Oak Bluffs at 7:30 am and arrive in Woods Hole at 8:15. Pick up your rental car needed for the remainder of this trip from the Falmouth Steamship Terminal and drive to Providence.

Read Things to Do in Providence Rhode Island

Day 10 and 11: Newport Rhode Island

Newport Rhode Island is famous for its Gilded Age mansions and America’s Cup competition. You will find mansion tours, a gorgeous harbor full of yachts, a cliff walk, lighthouses, Easton’s Beach, Bowen’s Wharf, Bannister Wharf, Thames Street, and many sailboats. Plan to visit two mansions a day, and purchase a discounted pass from the Preservation Society here.

Read 48 Hours in Newport Rhode Island

Day 12: Mystic Connecticut

Mystic Connecticut was made famous by Julia Robert’s first major role in the movie Mystic Pizza. You will find a historic seaside town, Mystic Seaport Village living museum, the Mystic Aquarium, and Beluga Whales, movable bridges, souvenir shops, apple cider donuts, lobster rolls, and more. Consider booking a Beluga Whale experience at the Mystic Aquarium and be sure to eat a slice of Mystic pizza.

Read One Day in Mystic Connecticut

Day 13: Plymouth Massachuttes

Plymouth Massachusetts has been called America’s hometown. You will find the famous Plymouth Rock, the Mayflower, Pilgrims, cranberry bogs, lobster rolls, breweries, distilleries, and wineries. Be sure not to miss learning how the first Pilgrims lived at Plimoth Plantation living history museum.

Read Things to Do in Plymouth Massachusetts

Day 14: Return Flight from Boston Massachuttes

Return to Boston and drop the rental car off at Boston Logan International Airport. Return to the city and check into your hotel for one final night. Do last-minute sightseeing missed the first few days of the trip and stop at Faneuil Hall Marketplace for a final lobster roll or bowl of Boston Clam Chowder.

Be sure to check the Massachusetts , Rhode Island , and Connecticut Office of Tourism for upcoming festivals, special events, and what’s happening during your stay.

Bookmark and Pin Two Week New England Road Trip Travel Guide

Best Booking Resources for a New England Road Trip

New england travel guide.

Download an ebook, phrasebook, map, or bundle directly from Lonely Planet , or pick up a New England Travel Guide from Amazon.com to browse on the plane.

Book Your Accommodation in New England Now

Spending the night? Search Booking.com and VRBO in one place to find to perfect property!

New England Attractions and Day Tours

The best attractions sell out! Don’t chance it, get your tickets now and relax when you arrive.

Travel Essentials

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Have a great vacation!

I have visited Boston and I did really enjoy the city but I didn’t get to see these other places close by. I would love to do this road trip as I have heard of many of these places and they do look beautiful. I love the Gingerbread Houses and would love to see provincetown. I can’t wait for my next road trip around the USA and to include these places.

I was able to watch the salmon and it was great!

This looks like a perfect 2 week trip to New England. Good idea to explore Boston and Salem by public transport and use a rental car to get from one place to another at other times. Actually we have been thinking about a similar road trip to New England for a while now – so I am going to save your post for reference! Thanks!

My nephew stays in Boston and we are planning a trip end of the year to be with him. Hence this post is a great insight into New England. Love road trips and the beautiful photographs that you have posted here gets me excited formy trip.

I really enjoyed this guide Sherri. I’ve never visited this side of America before and it’s so interesting. I think because I like the history and the probably read about Nantucket and Boston too. Plymouth looks so pretty and has a lot of history!

New England is a tourist spot with activities galore. Right from exploring the Boston tea party museum, the impeccable Ginger bread houses at Martha’s vineyard, the famous lobster rolls, breweries, cranberry bogs, sailboat wharfs and learning how the first pilgrims lived in Plymouth plantation, New England is rich with heritage.

That is a complete guide on New England – from how to get there to best time to go and what places to visit. I am all for Salem – would love to experience the witch era here. And Nantucket looks interesting too. As for Martha’s vineyard – have read so much about it in various novels. Time I get to it.

We definitely need to plan a New England road trip. So many great stops on this trip we have not yet visited. But I would definitely plan to visit when the crowds were smaller. Some great reasons to pick up both Rhode Island and Connecticut.

This sounds like a great road trip and one that might be ideal in the fall with the changing of the leaves. I like that it is a mix of city with Boston to the charming small town of Providence Rhode Island and then to be close the water in Nantucket.

I love this part of the US and we visited it extensively when our son lived in Connecticut. It’s indeed loaded with American history, beautiful architecture and scenic places. My favorite were the mansions in Newport Rhode Island. Wow! I’d love a summer house like that! This was a very nice 14 day road trip itinerary.

Great idea to include all the details of an itinerary here including exactly how to get from one place to the next! You’re right that most people don’t have the time or want to take the time to plan all the details. Your photos made me want to go back I loved exploring Boston and also visiting the Plimouth Plantation many years ago.

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Road Trip New England: See Six States In Two Weeks

A road trip to New England is perfect for any season, with plenty of activities to indulge in.

Quick Links

Day 1 & 2: boston, massachusetts, day 3–5: maine road trip, day 6 to 7: white mountains and mount washington in new hampshire, day 8-9: southern vermont road trip, day 10: the berkshires, northwestern connecticut, day 11: newport, rhode island, day 12 to 14: drive to cape cod.

Bestowed with towering mountains, quaint architecture, picturesque seaside towns, and, of course, the wonderful fall foliage when the once lush green trees turn into vibrant colors, New England is hands down a unique travel destination where one can take an epic road trip with friends and family. Right in the northeastern part of the USA, New England is made up of six diverse states, including Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island.

This beautiful region of North America was named by Captain John Smith, who explored its shores in 1618 for some London merchants. It was a strategic region in the 18th century when the revolution for independence from Great Britain took place to establish the new nation of the United States of America. While there are many historical places to visit, New England is also endowed with scenic landscapes perfect for exploring on a road trip in 14 days.

One of the most convenient places to start the New England road trip is Boston, which is the biggest city in the region. Its main airport, Boston Logan International, is very accessible, and one can easily find a vehicle to rent for the trip.

Those who enjoy a little bit of a historical tour can visit the 2.5-mile Freedom Trail to learn about revolutionary history. The trail encompasses 16 key locations marked largely with brick that lead through the North End to the Bunker Hill Monument, known as the first stage of the American War of Independence .

For a lunch break, consider taking a food tour at Boston’s Italian North End, praised for being a food lover’s paradise, where one can find a range of restaurants specializing in Italian dishes.

On the next day, take a leisurely ride on a swan boat at the Boston Public Garden, designed by Frederick Law Olmsted. The garden is made up of over 600 varieties of trees and gorgeous flowers. Soak up the fresh air and enjoy the peaceful setting. Then spend the afternoon taking a stroll down the cobblestone streets in historic neighborhoods such as Louisburg Square and Chestnut Street to take some nice photos. Along the way, visit quaint shops, cafés, and restaurants.

• Bunker Hill Monument Opening Hours: 10:00 am - 04;30 pm (Friday and Saturday); 10;00 am - 04:30 pm (Sunday) and close on Monday to Thursday.

Related: A Guide To New England's Most Festive Holiday Events

After a four-hour drive from Boston, check out Maine, where one can expect to enjoy scenic road trips leading to wonderful attractions, including seafood restaurants or lobster shacks, which this place is known for.

Maine is also popular among leaf peepers for its scenic fall drives . And in summer, one can think of its sandy beaches, such as the one found in Ogunquit ( which is a perfect Portland alternative) , to take a boat trip or enjoy a sunset cruise. There are many activities, such as whale-watching or visiting Perkins Cove, a small fishing village.

Another recommendation is to visit Cape Elizabeth, a place loaded with history, adventures, and a sublime coastline. Take a tour of the iconic lighthouses, including the Cape Elizabeth Lighthouse, also known as the "Two Lights," and located at the southernmost entrance to Casco Bay. The lighthouse is a good example of Gothic Revival architecture. Nearby is Two Lights State Park. Ram Island Ledge Lighthouse is another option to consider when visiting Maine. These places are perfect for taking a lunch break while enjoying the crashing waves.

• Tip: Check out Acadia National Park if time permits. Those planning to catch the sunrise on Cadilac Mountain try to head there early to see the first sunlight.

When it comes to New Hampshire, one can think of winding forest roads leading to the White Mountains, charming little towns filled with immigrants' heritage, and rugged coastlines. There are a lot of things to do in New Hampshire. Take Highway 112 to enjoy the breathtaking views of the landscape and scenic stops, where one can enjoy a short hike through winding rivers. Head to the White Mountains Visitors Center at Exit 32 off I-93 in North Woodstock to get free brochures and maps.

For the next day, those who wish to get more adventurous can consider hiking Mount Washington, the highest peak in the Northeastern United States, reaching 6,288.2 ft. Right at the summit, one can bask in the incredible view of New York’s Adirondack Mountains.

• White Mountains Visitors Center : 200 NH-112, North Woodstock, NH 03262, United States
• Hours of operation: 8:00 a.m.–5:00 p.m.

Discover the authentic villages, art galleries, and farm-to-table restaurants in the beautiful valley when taking the Kancamagus Scenic Byway to Woodstock. The scenic drive is best known for the fall foliage season and is a designated American Scenic Byway for its history (think historical Indian land and the legacy left behind by the railroad workers), aesthetic beauty, and culture.

• Tip: Check out the 1880s pink sandstone Norman Williams Public Library and Billings Fram & Museum in Woodstock.

Explore the other side of the Berkshires in northwestern Connecticut that stretches from the Upper Housatonic Valley to the Berkshires' foothills, where one can find the 21 towns of Litchfield Hills. Here, one can expect to find spellbinding waterfalls, rolling hills, and village greens listed on the National Registry of Historic Places since 1968.

The historic district exudes the charm of 18th-century New England in a bucolic setting. There are many opportunities for indulging in outdoor activities such as hiking or driving through the rolling farmland.

• Tip: There are many wineries to visit; one of the most popular is the Hopkins Vineyard.

Next, visit Newport, Rhode Island, to see the iconic Gilded Age mansions that were once used as summer retreats for America's elites. Take a historical tour of these mansions, which have now been converted into museums.

Related: A 3-Day New England Itinerary For Gilmore Girls Fans

After visiting Newport, head to Cape Cod to enjoy the breezy beaches, visit the lighthouses such as Nauset lighthouse, and spend time soaking up the fresh air. Take advantage of the laid-back setting and choose to spend the entire day relaxing at the beach.

Relish scrumptious seafood at local restaurants, and then take time to explore popular attractions such as the Heritage Museums and Gardens, Nickerson State Park, and First Cush Winery.

After spending the last days on Cape Cod, return to Boston by making stops in one or two villages.

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

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With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

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Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Find a Lincoln Airbnb or stay in North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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Your Perfect New England Road Trip Itinerary: Plan a Road Trip From Boston

May 6, 2021

Start with a road trip from Boston.  Mix lighthouses, whaling ports and clam chowder with the origins of modern America with this New England road trip itinerary. By the end, America may seem older but you’ll feel younger.  Here’s how to make it happen.

Table of Contents

The Perfect New England Road Trip From boston

New england road trip itinerary map.

A Two Week New England Road Trip Itinerary

This New England road trip itinerary follows our well-researched plans. We spent two weeks driving around Massachusetts, spending a few days in Boston and then looping through three key areas: Salem and Cape Ann to the north of Boston, historic Plymouth, Cape Cod, Martha’s Vineyard and Nantucket to the south and then inland to endless tree-lined roads in the Berkshires.

Separate stories of the people we met and the stories we uncovered will come elsewhere on the lab ( see the USA section here ), along with poetry, whimsy and the story of the invention of the first ever fried clams.

Whether you’re at the dreaming, planning or booking side of things, I present you with a nuts and bolts New England road trip itinerary to help you plan your perfect road trip from Boston.

From Massachusetts to Manhattan and Brooklyn

Another great idea is to extend your Massachusetts road trip into New York State. Brooklyn is one of the most densely populated urban areas in the world and intriguingly diverse: over 60 languages spoken in the area.

It’s also known for being an artistic hub, and a great alternative place to stay to cross the bridge and explore Manhattan. Here’s a lovely example of a boutique hotel in Brooklyn to add to your road trip plans.

Boston: Days 1-3

Spend a few days in Boston recovering from jet lag and enjoying this historic, thriving, curious, famous city often overshadowed by nearby Manhattan.

• Recommended reading: Things to do in Boston and beyond .

Salem and Cape Ann: Days 3-5

The first stop on this New England road trip itinerary has history and white picket fences written all over it.

Salem’s most famous role was as the heart of the infamous Witch Trials of 1692, brought to 20 th century audiences (and schoolrooms) through Arthur Miller’s The Crucible and a subsequent performance by Winona Ryder.

The first part of the Salem Witch Museum explores story of the original trial. But even more interesting than that is the second section. Here, the conversation moves to the idea of a “witch hunt” and the process through which society mistrusts and demonises “outsiders.”

The Salem Witch Museum really isn’t suitable for children under 8. It’s dark with screaming, animated, figures and a human-size devil, so it’s the one thing I’d recommend families take in turns or skip.

Cape Ann is a gorgeously rural, windswept place with pebbly-sand beaches that lift the soul at dawn. What’s even better? You won’t find many tourists here, at least not from outside America.

As a result, a visit to Cape Ann is all about taking in nature and local customs and really slowing down.

As so many events are weather dependent (and you rarely need to book) I’d advise you look at a map and mix and match from the following. You should be able to fit everything in within a couple of days.

Watch Sunset at Pigeon Cove

This gorgeous spot has been entertaining guests since the 1850s when William Norwood set up a tavern carriage traders. In its time, it attracted literary greats like Ralph Waldo Emerson (“Trust thyself”) and Henry David Thoreau so you can feel englightened as you dine (toddler included.)

• Book your spot at Emerson Inn here.

Spend the Day at Appleton Farms

Nine generations of Appletons have worked on Appleton farm , amid crumbling stone walls and one of the earliest American dreams. That makes it one of the oldest continuously operating farms in America.

Today, it’s part of the Trustees for Reservations Group (a kind of American National Trust.) Overall, Appleton aims to bring the wholesome, heritage parts of farming to city slickers and those who want to get involved.

It spreads over 1000 glorious acres of rolling grasslands and maple trees, like scenes from Jed Bartlet in New Hampshire in the West Wing. But it’s not just pretty for the tourists.

It’s a working farm and you can visit livestock, hike for hours or visit the historic farmhouse.

Catch the afternoon milking of the Jersey cows at 4:00, say hello to the chickens, goats and sheep at any time. And if you’re lucky, catch a cheese-making demonstration at the creamery.

Visit the Singing Beach

Manchester’s Singing Beach has a poetic name for a poetic place. The sea may not actually sing (it’s more like a whistle) but its sense of peace was one of the highlights of this New England road trip itinerary.

Go for Dinner or Cocktails at the 1606 Restaurant, the Beauport Hotel

Join the much-feted East Coast Elite in the glory days of shipping by dining at 1606 Restaurant at the Beauport Hotel. The restaurant overlooks the sea, with a luxurious nautical theme of polished wood, white walls and knotted rope. Seduced by the gentle live music, it’s easy to believe that you too could run for office one day…

Visit the Birthplace of Fried Clams

At the other end of the spectrum is Woodman’s of Essex , the self-proclaimed “home of the fried clam.”

It’s a lovely story told by lovely people. In 1916, Lawrence “Chubby” Woodman, at the suggestion (near dare?) of a friend, decided to fry some clams ahead of the national July 4 th celebrations. Five generations and over 100 years later, the clam shack is still going strong, and the legacy of the fried clam has spread across New England.

Here, you grab a seat with friends and tuck in to a range of fried fare, including the state’s iconic clambake and the fresh lobster for which New England is so well known.

Where to Stay in Cape Ann

We stayed at the Castle Manor Inn , a lovingly restored Victorian Inn just made for flowery dresses and Instagram. It’s situated inland, with soothing green gardens and that mix of grandeur and homeliness that buildings of that era exude.

While atmospheric, it’s probably not the best choice for young children as there’s no crib or soundproofing. But, if you’re travelling as a couple, it’s romantic, and if solo, a good place to chat over breakfast on the narrow terrace. And the staff couldn’t be friendlier.

Plymouth, Cape Cod and the Islands: Days 5-11

Now it’s time to visit all those places you’ve heard about in half-whispered dreams, novels, schoolrooms, history books and anything that probes into the life of J.F.K. Plymouth, Cape Cod and the islands.

Plymouth is where America began. Kinda.

It is where the pilgrims settled (they landed at Provincetown), and it remains the oldest continuously inhabited settlement in the United States founded by Europeans. Others may have got there first, but this was the only one to last.

Its history is fascinating and complex; its layout restfully small. It’s a walkable, beautiful grid of artsy coffee shops, bobbing boats and impressive, historic brick buildings.

But before you get there, allow your New England road trip itinerary to stop off at World’s End in Hingham and the cranberry bogs along the way.

World’s End

This unexpected wilderness between Boston and Plymouth offers a chance to get back in touch with nature and see views that haven’t changed for centuries.

Managed by the Trustees (the same ones who manage the Appleton farms), World’s End involves over 250 acres of tree-lined avenues, rocky shores, steep hills and wild grass.

Look one way to see Boston, its skyline painted in faint, pastel colours. Look the other to see a Nordic fishing village which turns out to be the New England coastline.While the buildings of New England may be old in US terms, this place is even older.

Linked to the retreat of the same glacier that led to Boston Harbor, the salt marshes and spoon shaped hills (or drumlins) look the same now as they did thousands and thousands of years ago.

The Trustees hold concerts here on a summer’s day, but, even if grey clouds roll in, a stride between the granite ledges, red cedars and blueberry thickets make the perfect exercise break on a road trip from Boston.

The Cranberry Bogs

Yes, when I heard about cranberry bogs I wasn’t that impressed.

Yes, when I saw a photo, I completely changed my mind.

Cranberries are big business in New England, with U.S. Farmers harvesting approximately 40,000 acres of cranberries each year. What makes this farming industry so much more interesting than the rest are the shimmer of the cranberry bogs come harvest time.

Full of bright red berries as far as the eye can see, farmers flood the bogs with enough water to cover the vines that carry the berries. They then use water reels to knock the fruit off and collect them with conveyors or pumps.

Alas, for international visitors, the season is short, running from approximately mid-September to early-November each year.

We stopped off at Mayflower Cranberries LLC (call ahead if you wish to do the same) in Plympton, Massachusetts to speak to owner Jeff LaFleur.

An amiable, passionate man, LaFleur has taken cranberry farming to the next level. His 112-acre farm  has 236 acres of active cranberry bogs and he’s also a grower-owner for Ocean Spray Cranberries. As an aside, I had assumed that this was a big, faceless, awful corporation before this visit, but it’s actually a pretty decent co-op that benefits small farms and keeps them in trade. Jeff is a fan!

In Plymouth, you can indulge in as much or as little history as you like. Unless you’re particularly keen, though, one full day is probably enough. Spend the day from Boston to Plymouth stopping off at World’s End and the cranberries, and then give yourself one full day in Plymouth itself before driving on to the Cape.

The Plimouth Plantation is a little way out of town, but everything else is easily walkable, and it’s really the best way to get a taste of the place.

Plymouth Rock is New England’s most visited rock (drawing in more than 1million visitors each year).

This historical landmark signifies the place where the Mayflower pilgrims began Plymouth Colony, which is essentially the first permanent European settlement in New England.

You’ll find Plymouth Rock in the peaceful Pilgrim Memorial State Park on the shore of Plymouth Harbor.

The Plimouth Plantation

The open-air museum that is the Plimouth Plantation really turns the traditional idea of the American thanksgiving around.

Two villages co-exist:

• the Wampanoag settlement with trailing smoke, simmering cauldrons, feathers, paints and spears.
• the pilgrim settlement, where actors have British accents and talk about their journey from Leiden in Holland where they were granted asylum before they left ”to find the new world.”

A Tale of Two Sides

From a fraught narrative, the Plantation showcases both sides of the American story without passing judgement. Leave at least a full afternoon to really make the most of it.

Where to Eat in Plymouth

• Kiskadee Coffee Company – for local art, simple snacks and, well, good coffee.
• The Water Street Café – head to this diner for an all American breakfast you’ll never forget. Order crunchy French toast and consume more calories in one sitting than you even do at Christmas. Guilty. Delicious. Fun.
• Dillon’s Local – we enjoyed this so much, we went back twice. ;-)  Cosy, yet hipster eatery with classics like New England clam chowder and more modern arugula grilled peach salad.

Where to Stay in Plymouth

We stayed at the John Carver Inn & Spa , right within walking distance of town.

It’s a curious spot, with a mix of themes and styles, but rooms are spacious and well stocked. There’s a fantastically outrageous swimming pool with a full size replica of the Mayflower (with a bit of artistic license!).

After you check out, it’s time to grab your swimwear and prepare to head to the Cape…

Cape Cod and the Islands

This is the section of a Boston road trip that takes the most planning before you go.

But, oh my, is it worth it.

There is a spirit around the Cape that is simply unique. The curling tip of land that tickles history, the roar of the waves and the sharks that circle around. The taste of the air and the stick of the salt and the sense that adventure and the open world wait just around the corner.

And truthfully? We should have planned a little better and given ourselves more time. Not because there are so many things to do (there aren’t really), but because this is a place to slow down and not really think about things to do.

• Recommended reading: how to plan a road trip by yourself

Fitting the Pieces Together For Cape Cod and the Islands

• Station yourself in Hyannis, the hub of the Cape. While not the prettiest part, that’s a bit like saying Monet’s poppies aren’t as pretty as his waterlilies. It’s also close to the ferry port, making those connections far easier.
• Don’t take your car to Nantucket.
• I know I keep mentioning this,  but it’s important. Parking is tricky there and getting the car onto the ferry is even trickier.
• I’ll write more about these areas separately, but for now, here’s the key information to help you plan your visit.

The Cape Cod National Seashore

Managed by the National Parks Service, the Cape Cod National Seashore area cuddles along the curve of the Cape, flanked only by majestic Atlantic pine, sand and the odd shark.

Arrive early as parking is limited and expensive so it makes sense to stop for a while.

Glossy, well-heeled Chatham is a delight to walk around in between its sassy book shops, art galleries and antique shops. At the “elbow” of Cape Cod, this is the point where Nantucket Sound and the Atlantic Ocean meet.

There’s easy access to a windswept sandy beach with a lighthouse that dates back to 1878. And if you’re in luck, you can catch the annual shark art festival:

Where to Eat in Cape Cod

Twenty-Eight Atlantic at Wequassett Resort  –  Fine dining with full views of the sea. Look out for the ash-roasted cod loin and Chatham shellfish company oysters.

The children’s menu also comes as a sail on a wooden boat and table lights come inside hollowed sea urchins.

Twenty-eight Atlantic enjoys the highest ratings on Cape Cod from Forbes, AAA, and Zagat and it’s easy to see why.

Where to Stay in Hyannis

We stayed at the Anchor In , a convenient spot in Hyannis with spacious, light rooms, well-informed staff and a small outdoor pool with a view of the marina. A cosy “old New World” library serves breakfast and drinks through the day as well.

How to Get From Hyannis to Nantucket

We travelled with Hy-line cruises. The journey is short (136 minutes) but leave plenty of time to board and book your ticket in advance.

There’s a small café on board and an easy chance to walk around for toddlers.

Oh, how I loved Nantucket. I Really, really loved the place.

This small island, only 30 miles across, seems to tell the story of human innovation and reinvention through a series of picturesque beaches, stylish place to stay and chic spots to eat.

Architecturally, little has changed from the 17 th century whaling hey days, all wooden slatted town houses and white columned porches.

Once it was one of the wealthiest spots in the world, thanks to its whaling industry.

Today it welcomes tourists and grapples first hand with balancing the past, the future, sustainable tourism and identity. Nearly 40% of Nantucket is protected for conservation and the island is now a National Historic District to boot.

All of which sounds far too serious for what is, essentially, a gentrified beach resort. But that’s what makes it so interesting.

Visit the   Whaling Museum to uncover a striking, poignant, provocative and unapologetic look at the realities of the whaling industry and why it was so important to the world at that time.

Finding the Beach

Brant Point is a short and easy walk from Nantucket’s centre for an iconic lighthouse shot and scuff in the sand. Watch the ferries glide in and think back to the whaling past. Don’t try to swim, though. Currents here are far too strong.

The Children’s Beach is even closer to town with a playground and kids activities on in the summer.

For further beaches and exploration, hire a bike and cycle away!

Where to Stay in Nantucket

We stayed at 76 Main Hotel. This gorgeous little bolthole forms part of a small local chain, called/run by Lark Hotels.

Stylish inside and out, rooms are small but deliciously designed.

There’s even a private firepit to help you embrace another Nantucket custom: melting marshmallows, biscuits and chocolate to build your own s’mores…

Martha’s Vineyard

After Nantucket, Martha’s Vineyard seems enormous and urban. But of course, in reality she’s only 25 miles across with a population of around 17,000.

Her villages have different character, but you’ll find a key blend of summer holidays and New England in each.

You can catch the ferry from Hyannis but we drove from Hyannis and picked up the Steamship Authority ferry from Woods Hole to make the next part of the journey a little easier.

Arrive in good time to queue with your car but again, there’s a café and room to walk around when on board. And some spectacular views as you approach the island.

What to Do in Martha’s Vineyard

A trip to Martha’s Vineyard forms an essential part of any New England road trip itinerary. Here are the highlights:

• Look out for Murdick’s Fudge
• Visit Tuck & Holand Metal Sculptors at the Vineyard Haven Gallery to meet the man who makes weather vanes for the stars (Steven Spielberg has a velociprator made on this very island.)
• Feel the salt in your lungs and the wind in your hair on Martha’s sandy beaches.
• Pay a quick visit to the pastel-pretty gingerbread cottages in Oak Bluffs.
• See the wealth of the whaling captains in Edgartown, Martha’s first colonial settlement, through their Greek revival mansions.
• Give Mad Martha’s ice cream a good licking. With a fun name like that, you may as well try one.

Where to Stay in Martha’s Vineyard

The Winnetu is the kind of place I’d love to stay at all week for one of those relax-and-forget-about-the-world holidays – with children.

It’s unusual in that it is designed with families in mind – and yet it still manages to be pleasing to the eye for adults!

Rooms have decent high chairs, cots and mini self-catering facilities but with a beautiful, New England design that appeals to adults.

The Dunes Restaurant introduced a new concept to me: adult dining with a children’s play area within the restaurant (if you don’t have kids, don’t fear, there is an adults-only section.)

The hotel’s outdoor pool is set in spacious grounds with a lifeguard and towel service and seemed surprisingly, blissfully empty for the most part. The great, green grounds led to the ocean at South Beach where it was too blustery for us to go in but seemed majestic in its beauty.

From Martha’s Vineyard to the Berkshires and Around: Days 11-14

Get ready to welcome manicured, college campus America, with a side stop into the edgier Springfield, home to the Dr. Seuss Museum and the man himself. In fact, the key draw to this region (for me) was the “Iconic Illustrators Trail” – an intriguing journey through different areas of New England, each with amazing images.

From Martha’s Vineyard to Springfield

We took the ferry from Martha’s Vineyard to Woods Hole as it shortens the driving time as compared to a return ticket to Hyannis. Check which makes the most sense for you.

Springfield was a surprising stop on this New England road trip itinerary. It broke the classic “New England” style and probably deserved a little more exploration.

Local boy Dr. Seuss (real name Theodor Geisel, ) grew up here amid the thriving inner-city medley of life with newly arrived immigrants from around the world. And The Amazing World of Dr. Seuss Museum shows how that background developed into a world-famous career through personal artefacts, photographs and handwritten notes.

However, the real scene-stealer is the whimsical area downstairs, where characters like the Lorax greet you in life-size form. It is aimed at and perfect for children.

Where to Stay in Springfield

We stayed at the Tower Square Hotel , a tall, slick city affair with a suite that had a separate kitchen that would have been a godsend if we’d still been weaning (it was still pretty good as we could have some family time after baby lab went to sleep in our room.)

There’s a pool with a sporty feel on one floor and an all-American breakfast available in the basement. Concierge parking and a 24-hour reception desk marked a return to city life after the blue-and-white laid-back feel of the islands.

Where to Eat in Springfield

Adolfo’s, just around the corner from the Tower Square Hotel , offers tasty, unpretentious Italian food with a local twist. Look out for the owner’s legacy on the walls…

Springfield to Amherst

What’s the reason to stop off in Amherst? Why, the Hungry Caterpillar Museum .

Of course, its real name is the Eric Carle Museum of Picture Book Art and it celebrates the work of illustrators across the world. The library arranges books by illustrator rather than author and there’s a huge room dedicated to getting arty and involved with crafts.

Local Flavours in Amherst

Just down the road is the Atkins Farms Country Market , a supermarket come delicatessen come restaurant that showcases the local farming produce. And it’s amazingly tasty.

Perfect for stocking up for picnics or dropping in for a bite to eat.

From Amherst to Northampton

This short journey only takes 20 minutes. Check in and enjoy the evening. There’s more exploring to do tomorrow.

Where to Stay in Northampton

We stayed at  The Hotel Northampton . Looking for a taste of American history? This is it.

Eleanor Roosevelt, Jenny Lind, Herbert Hoover, Calvin Coolidge, Dwight Eisenhower, John F. Kennedy, and Richard Nixon all dined in the hotel’s restaurant,  Wiggins Tavern , in Northampton.

Rooms are moderate sized and blissfully quiet, with cots on request and a breakfast to make Americans proud.

There’s also a fantastic toy shop across the street, with the loveliest staff. They found us lightweight building blocks that stick together without glue. Perfect for travelling. Just as an aside ;-)

Where to Eat in Northampton

Bistro Les Gras – It’s a gorgeous sunset walk through Northampton to reach Bistro Les Gras, where locals dine for special occasions (they came, they chatted, they told us.)

Amid low lights and American-French charm, try the wild gulf shrimp and lemon tart. If you have a wriggly toddler with you, it’s easy to pop out and visit the live music opposite.

The Normal Rockwell Museum

The Norman Rockwell Museum tells not only the story of the world famous artist but also, in a way, the story of 20 th century America as well.

Photos, paintings, and the painstakingly relocated office of the man himself offer an insight into an America that laid the foundation for the one of today.

Tanglewood & Lenox

Tanglewood is a place to get your music groove on, as long as there’s something on. The 210 acres of the Tanglewood estate  were given to the Boston Symphony Orchestra in 1936 by Mary Aspinwall Tappan and the result is half stately home gardens, half rock and roll concert venue.

Even if there’s not a concert going on, you can get in and look around.

Where to Eat Near Tanglewood

Lenox is another quintessential small New England town, with boutique art shops, white fences and cute places to eat.

Tanglewood to Deerfield

The last stop before returning to the hubbub of either Boston or its international airport is the leafy, quiet village of Deerfield. Here, historic mansions rise into the sky with the trees in this 18 th century village that simply froze in time.

Where to Stay in Deerfield

Book in advance to stay at the Deerfield Inn , right in the heart of the historic part of Deerfield. Guest rooms wear period florals, lamps and bedspreads and the dark wooden writing desks seem from another age.

Deerfield to Boston

And so, this rather epic Massachusetts road trip comes to an end.

But there’s one last stop en route to the airport: Louisa May Alcott’s house .

The author of the international bestseller published in 1868, lived here with her three sisters and parents on the outskirts of the small town of Concord.

It’s a heart-fluttering stop for literature but it also shines an interesting spotlight on society in New England at the time.

How to Make It Happen

Driving is easy in Massachusetts, even if you’re used to driving on the left. Signs are clear, fuel is easily found and all the signs are in English.

America is a country built on transport, and the love of the automobile runs deep. It is more or less expected that you’ll drive everywhere and, as a result, parking is plentiful and cheap (and public transport tends to be sporadic and awkward.) It’s one of the reasons why this New England Road Trip itinerary works so well!

Explore Our Road Trip Planner & Toolkit

Designed for those who love to travel but who hate spreadsheets, our Road Trip Planner & Toolkit system shows you a bulletproof formula for getting organised in half the time. Plus, it includes the one innocent mistake that even seasoned travellers make.

The key exceptions to this are in Boston (a big, old city where walking and public transport will serve you best) and the island of Nantucket (where cars are virtually forbidden.)

Access to the beaches at Cape Cod also require hefty parking fees as the place is so popular and the villages so small.

By and large, though, Massachusetts, like so much of America, is built for a fly-drive holiday.

Where and When to Pick Up Your Car

Spend a few days in Boston, soaking up the accent, the red-brown leafy streets, the education and the arty brunches.

Then pick up your car either at the airport or at one of the centres in town. Unlike most cities, Boston Logan International is quick and easy to get to, so if you plan on flying straight out at the end of the trip, then it’s cheaper and easier to drop off at the airport and go.

Car Hire With Perks: Hertz Gold

We rented a car through Hertz . The booking and collection process was simple, but what makes the service even better is that they have an  American Road Trip Planner . It makes drafting itineraries so much easier.

It’s perhaps not a great way of calming wanderlust, but it does mean that you can quickly plan another trip; an ideal way to beat the travel blues in my opinion

If you register with  Hertz Gold Plus Rewards BEFORE you make your reservation you receive better deals, the chance to skip the queues and to use the Gold Plus Rewards counter. It’s free to register and only takes 60 seconds, so it’s worth doing.

What You Need to Plan in Advance

If you really have your heart set on something in particular then it makes sense to book it as soon as you can.

For me, though, most of the joy of travel involves a certain level of spontaneity and exploration, to follow where I want to go and (excuse the cheese) allow the essence of the place to appear at its own pace.

That said…in Massachusetts there are some things you really need to book in advance.

• Ferries and accommodation on the islands of Martha’s Vineyard and Nantucket are often in short supply, with a fixed number of nights bookings and timetables that you need to stick to.
• Leave your car behind as you head for Nantucket (leave plenty of time to find a parking space in Hyannis as it’s a bit of a scrum. Enterprising householders nearby charge a hefty fee to let you use their driveway.)
• Boston can also book up quickly and so the sooner you can nail down your accommodation and car hire there, the better.

Lock these down first then work backwards from there.

Booking Flights to Boston

Our partner for this trip, Norwegian, has increased services to Boston with a daily non stop service between London Gatwick and Boston Airport. The flights are operated by a fleet of brand new Boeing 787 Dreamliner aircraft with two cabins in premium and economy.

Fares start from £155 one way / £259 return in economy and £415 one way / £745 return in premium, including all taxes and charges.

To book visit  www.norwegian.com/uk  or call 0330 828 0854

Wifi On the Road

It would be optimistic and slightly romantic to think that mobile internet isn’t needed for a road trip. It’s near essential for navigation, for looking up nearby restaurants and opening times and great for contacting people back home.

Mobile internet can be expensive, though, not to mention a pain to set up if you have to get a SIM card at the airport.

We rented a mobile wifi device (aka a MiFi) on this trip. It’s really convenient for family trips because everyone can join a single device instead of replacing all your SIM cards. You also get to use your original phone number so you don’t have to worry about the logistics of checking two numbers or letting loved ones back home know.

Mobile Internet from Cellhire

Cellhire is a world leader in mobile communications , allowing travellers to stay connected all over the world. The USA MiFi is one of Cellhire’s most popular products. It’s well-loved for its instant data connectivity abroad, super-fast 4G speeds and its 5GB and 10GB bundles. The USA MiFi starts at as little as £50 a month.

Should I Travel to Massachusetts with Children?

Yes, a resounding, yes! People are friendly, polite, services work, healthcare is great and driving and parking is easy. This is America, after all. :)

However, while Florida and Louisiana seemed enthralled by our smallest travel companion, some (only some) areas we visited in Massachusetts seemed a little more reserved.

We were warmly welcomed at fine dining establishments, museums, on flights and in hotels but I’d just say that the difference between Massachusetts and the South was like the UK and the Med. Children are  adored  in the south, welcomed further north.

Adding More States To Your New England Road Trip Itinerary

This New England road trip itinerary focuses on Massachusetts, without apology. It’s aimed to maximise your time out exploring if you only have two weeks available, which is the standard setup for travellers from the UK.

More East Coast Road Trip Routes Along the New England States

However, there is so much more to New England than Massachusetts.  By definition, it includes six states rather than one, and so add the names Maine, Vermont, Connecticut, New Hampshire and Rhode Island to your New England list.

Typically, autumn or fall is the time to make your way through these states, “leaf peeping” as you go. The colours are extraordinary, the maple syrup refreshingly sweet. There’s also winter sports and skiing in Vermont come winter and long hikes along the east coast for summer road trips. In my opinion, it’s better to take it slow and explore one area rather than trying to cram everything in. But to give you a few more ideas, here are some other New England road trips that explore the other states.

More New England Road Trip Itineraries

• Rhode Island – the state so small, you can drive across it in an hour. However, here are some Rhode Island Road Trip Itineraries that take in lighthouses, natural wonders and small villages, as well as Block Island.
• Here’s a road trip itinerary for Maine, taking in popular spots Portland, Camden and Park Loop Road just south of Bar Harbor in the Acadia National Park.
• Waterfalls, skiing and wine routes feature in these Connecticut road trip itineraries through the Litchfield Hills and New Haven.
• Explore the great outdoors of the Green Mountain State with these road trip itineraries for Vermont.
• And last but not least, drive around New Hampshire’s  Kancamagus Highway to the White Mountain National Forest. 

Keen to travel further afield but unsure where to go? Check out our guide to choosing between Los Angeles and Miami .

Beyond the East Coast: Other American Road Trip Itineraries

New orleans, louisiana.

Let the good times roll with this fascinating and fun road trip from New Orleans. Explore the less well known parts of Louisiana and learn more about America.

Florida, West Coast Itinerary

Flit from the beach to sweeping cool art museums with this Florida west coast road trip itinerary. Discover sleepy villages and a world away from the resorts.

The Great River Road, Louisiana

Explore the grandeur and the horror of plantation life with this road trip itinerary along the Great River Road in Louisiana. Then cool off amid the marshmallow in one of New Orleans’ best swamp tours.

Plus, check out how to plan your San Francisco to Santa Barbara road trip here.

Road Trip Planning Tools and Essentials

We love, love, love a good road trip here on Inside the Travel Lab and have driven solo, as a couple, a family and with friends all over the world. It’s such a great way to get off the beaten track and to feel the sense of freedom and exploration if only for a short while.

That’s why we’ve put together a series of tools and resources to help you plan your New England road trip.

For starters, don’t miss the 53 Road Trip Essentials checklist that covers what you need to pack. Then, sign up for our free road trip training sessions, a series of three videos to help you avoid the mistakes that I’ve made.

Last, but by no means least, check out our Road Trip Planner & Toolkit. It’s a revolutionary way to organise and plan out your road trip, without spreadsheets, lost scraps of paper, headaches and overwhelm. You can check that out here.

Anything else I can help you with? Just let me know!

Disclosure – This trip was made up of some self-funded aspects and a mixture of paid/unpaid partnerships with Hertz, Visit Massachusetts, Norwegian, and Cellhire. As ever, all opinions remain my own. Otherwise, what is the point?!

If you book or buy through links on this page, we may earn a small commission at no extra cost to you. Cheers!

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2-Week New England Fall Road Trip to the Less-Traveled

March 18, 2024 August 13, 2023

A New England fall road trip is what bucket lists are made of. I don’t care where you’re from but fall just hits differently in New England. 

If you time things right, you may just be able to follow the leaves from north to south. How magical does that sound?

What I’m sharing with you here is the route we took on our own adventures throughout New England .

Some of the stops here are likely destinations you wouldn’t expect on fall foliage trips throughout New England. We had cost and efficiency in mind, but I’ll make suggestions on alternatives and offer the more popular stops where appropriate, too.

Are you ready? Let’s get peepin’ with the ultimate New England fall road trip. (I’m talking about leaf peeping, friends.)

Disclosure: Please note that the post below contains affiliate links, including links through the Amazon Services LLC Associates Program. As an Amazon Associate, I earn from qualifying purchases .  At no additional cost to you, I earn a commission if you make a purchase. I won’t recommend something I have not used/would not use myself, and any income earned supports the upkeep of this site.

How many days do you need to see New England?

There is no minimum amount of days that you need to see New England. If you only have a long weekend, you can pick and choose what intrigues you and stick to one state . A week will give you a taste of the best New England fall foliage if you time things right.

This New England fall road trip guide will take you across all six New England states over the course of two weeks. You’ll get not only the best fall foliage but delicious eats, outdoor adventuring, and even tips on where the dog is welcome if you’re bringing a furry friend.

Note: Keep in mind that this is limited to New England fall road trips, as per your search request. You’ll see some jokers including states like New York in their roundups, which is fun but inaccurate. New York isn’t part of New England, so you won’t see Lake Placid represented here. I’ll cover all of the six New England states on this road trip!

How do you spend a week in New England in the fall?

You can spend a week in New England in the fall like this:

• Day 1: Woodstock, VT
• Day 2: Stowe, Waterbury, and Montpelier, VT
• Day 3: Lyndon, VT
• Day 4: Burnham, ME
• Day 5: Acadia National Park, ME
• Day 6: Bangor, ME
• Day 7: Rockland, ME
• Days 8-9: Portland, ME
• Day 10: Portsmouth, NH
• Days 11-12: Boston, MA
• Day 13: Providence, RI
• Day 14: New Haven, CT

How to Plan a New England Road Trip

Where is the best place to start the New England road trip? The best place to start the New England road trip in Vermont, arguably the most spectacular state when it comes to fall foliage. A Vermont fall road trip itinerary all on its own would be enough to give you that fall foliage fix.

How you get there depends on where you’re starting. We were driving from the Finger Lakes region of New York to kick off our fall road trip in New England. 

We were also on a two-month journey throughout New England, with long stretches of time in areas we felt might be conducive to slowing it down and getting some actual work done. This is then a truncated version of that New England tour.

As you’ll need a car for this excursion, if you’re flying, find an airport within a few hour’s drive that’ll offer you a decent deal. Albany, New York, is a good option, as it’s only a couple of hours from Woodstock, Vermont, our first stop.

Book a car well ahead of your travel from a price aggregator like Hotwire or Priceline . I typically just book the cheapest car, especially when I’m dropping it off at a different location than where I picked it up.

Interested in a map of everything I’ll highlight for you here over the epic weeks to come? Follow the Google link below:

GIMME MY NEW ENGLAND FALL ROAD TRIP MAP!

Day 1: woodstock, vermont.

Driving from New York, we stopped in Woodstock on our way to where we’d be staying the next little while: Lyndon, Vermont. I’ll get into that in a minute, but first, Woodstock.

This one is billed as the quintessential New England town. That also means the leaf peepers will be in full effect if you’re there for fall road trips in New England.

That’s OK. Embrace it. Crunch along some leaves. It’s a beautiful place. Woodstock highlights include:

• Downtown Woodstock: Start here to get yourself situated in Woodstock. You can stroll around to go tchotchke shopping at any of the nearby boutiques or walk off of Main Street for the most delightful architecture. Fall means spooky season, so find all of your favorite pumpkins.

• Sleepy Hollow Farm: If you want to peep at leaves against rolling pastures, head to Sleepy Hollow Farm. This is one of the most photographed rural spots in the country and has been here since the 1700s. Remind yourself of that history when you’re vying for a position with your camera.
• Sugarbrush Farm : Sample Vermont maple syrup and over a dozen different kinds of cheese at this third-generation family farm. The cheeses here come with a special wax coating to lock in all of that cheesy goodness and allow you to keep them for longer…although that sounds impossible to me.
• Marsh-Billings-Rockefeller National Historical Park: This is Vermont’s only national historical park, but it’s a beauty in the fall. Take a tour of the Marsh-Billings House and find The Pogue, a pond tucked away in Mount Tom Forest. Locals like to say it’s bottomless. Try to find out, or not.
• Middle Covered Bridge: This scenic bridge on Union Street was the first covered bridge built by the state of Vermont after 1889. It replaced an 1870s-era iron bridge that had been condemned for several years. I’m here for all the facts, people.

The small town of Lyndon was our base for Vermont, and we’d recommend it to see some excellent Vermont highlights within a short drive of town. It was also quiet and mostly void of leaf peepers, which pleased me very much. 

We’d also highly recommend it to see some excellent Vermont highlights within a short drive, including access to magical Dog Mountain for the pet owners amongst you.

Some of you may prefer to keep things efficient, and you have options for accommodations in Woodstock proper. The Woodstocker B&B would be my pick for a return visit. If you’re traveling as a couple, this one is adults-only. Guests love the fresh brioche in the mornings and warm cookies in the afternoons. It’s the little things.

Use the map below for more options:

Day 2: Stowe, Waterbury, and Montpelier, Vermont

It sounds like a lot, but I promise it can be done. All three towns are in close proximity to one another, and if you meet the crowds in Waterbury that we did, the much-talked-about whimsy of the place will die down a bit and cause you to flee elsewhere.

Start in Stowe. As soon as we left this town, I knew I had to go back. Brian loves to ski, so a repeat visit to check out Stowe Mountain Resort is certainly a possibility. I like to lounge, so a visit to Stowe during any season is a possibility for me.

If you have more time, check out my guide to Stowe . Otherwise, don’t miss these Stowe highlights:

•   Trapp Family Lodge : If you love Austria, you’ll love this property. You can hit several trails around the property for panoramic views, snack on brats at the Bierhall at von Trapp Brewing, or even stay at the lodge if you want to put down some cash.
• The Alchemist Brewery : Many beer lovers make the pilgrimage to Stowe to try Heady Topper, one of the most drinkable double IPAs you’ll find anywhere. If you’re visiting on a warm day, get yourself a can to enjoy in one of their Adirondack chairs. It’s blissful, basically.

• Gold Brook Covered Bridge: You may see this one labeled as the Stowe Hollow Bridge or Emily’s Bridge on your map apps. They’re all the same and they’re all lovely.
• Mount Mansfield: If you’re visiting up to about mid-October, you can drive to the top of Vermont’s tallest peak on the Auto Toll Road . The parking area at the summit sits at 3,850 feet, so the panoramas are lovely up there.
• Stowe Cider : I had a sour candy-infused Gummy Bears hard apple cider here that sounds like it should be a mistake, but it definitely wasn’t. Try a flight for a taste of some more unique or classic flavors. My fave was the High & Dry.

Waterbury is next and just a short drive from Stowe. It was quite thick with the leaf peepers by the time we got there mid-afternoon, but that’s what you get when you’re all cute and offering people all of the fall things.

This place has hot cider, hot cider donuts, all of the pumpkin things, and cheese. For a quickie visit, don’t miss:

•  Cabot Farmers’ Store : Sample all the Vermont cheddar you can handle and buy a novelty T-shirt while you’re at. I mean, that’s what I did, but do whatever strikes your fancy.

• Cold Hollow Cider Mill : When I was talking about all of the cider things, this is the best place in Waterbury to make that happen. If you’re traveling in a pair, have your honey stand in line for their legendary cider donuts while you browse the rest of the shop. Return when donuts are in hand.
• Craft Beer Cellar : This Waterbury beer shop is the spot if you’re looking for that one craft beer you had in New England back in the day. Their selection can’t be beat, or beaten if you’re some grammar purist.
• Prohibition Pig : Delicious meats and a good variety of craft beers are all allowed and welcome at this Waterbury eatery and brewery. Come for drinks or stay for smoked wings, brisket, or their epic whole hog group experience.
• Ben & Jerry’s : I’m not telling you to go to the grocery store and pick up some ice cream treats for your travels. This is the Ben & Jerry’s factory. It’s the only one you can tour in the country and is home to the hilarious Flavor Graveyard.

Montpelier was so close to Waterbury that we had to pop by for a visit if only to check out the state capitol. Here are some highlights in Montpelier with a few in nearby East Montpelier for good measure:

• Vermont State House : The golden dome on this capitol building is worth the price of admission. That admission is free, by the way, so if you want a guided tour you can make it happen at no charge.

• Hubbard Park: If you’re already visiting the state house, visit this 194-acre green space next. It’s a short walk just north of the capitol building to perfect picnic spaces and hiking trails if you want to stretch your legs.
• Coburn Covered Bridge: If you’re really into covered bridges, you should just move to Vermont because this state is just lousy with ’em. This one is the only surviving 19th-century covered bridge left in East Montpelier.
• Bragg Farm Sugarhouse & Gift Shop : It’s time to get a taste of pure and yummy Vermont maple syrup. This farm has been operating for eight generations. If you’d like to go on a guided tour, they’re free, but don’t leave before deciding on your favorite grade of maple syrup.
• Morse Farm Maple Sugarworks : I can’t just leave you here with just one maple syrup operation running for eight generations, can I? Here’s another. If you didn’t get enough of that sweet stuff at Bragg Farm, have yourself a few more samples at the Morse Farm.
• The Quirky Pet : Folks with pets won’t want to miss this place. It’s a pet shop essentially run by two mops and two kind humans who helped me pick out some bones and treats for Kimmy.

You have some options for accommodations tonight, but if you want to be in on the action for Day 3, stay near Lyndon just as we did. This country cottage in Lyndon is where we stayed during our own New England fall road trip. The layout was a little wild, but it was spacious and in a country setting that really fit the trip’s vibes.

If you don’t mind spending a bit more to stay in Stowe because you’ve fallen in love with the place, use the map below:

Day 3: Lyndon, Vermont

If you’re staying near Lyndon, you’re off the beaten path. Take advantage of that. Lyndon is a short drive to some pretty fantastic spots, namely Dog Mountain and Lake Willoughby.

I have a full love letter/ blog post on Dog Mountain that you can peruse at your leisure, but if you’re traveling with your pup, it’s basically a must. It’s a wonderland for dogs, and the only leash requirements are inside the gift shop.

Lake Willoughby is another must-stop if you’re already in Vermont’s Northeast Kingdom. It’s been compared to Norwegian fjords for a reason and likely won’t be one of the state’s most impressive hidden gems for long.

Fun fact: This dramatic landscape was carved out by glaciers. I’m telling you, this is one of those comparisons that tracks.

Stay another night in or around Lyndon at one of the properties I mentioned on Day 3, or return to your hotel in Stowe. If that’s the case for you, you’ll just have an extra hour of driving on Day 4.

Day 4: Burnham, Maine

You’ll have about four hours of driving today to Burnham if you stayed in or around Stowe. This will be your home base for adventures in and around Bar Harbor.

Why not just stay in Bar Harbor, you ask? Well, traveling regularly and in a regular fashion sometimes (er, usually) means you’re traveling on a budget. It’d be great to stay near Acadia National Park if you plan on visiting as we did, but you have to plan well in advance to find anything within a short drive of the park.

Note: I’m talking like, many months in advance, tacking on a few additional months for good measure if you’re visiting in the fall for that New England foliage.

It’s also expensive, especially if you’re traveling in the fall. I’m talking VERY expensive. If you’re good with that and would rather prioritize efficiency over cost, I feel you. I’ve been there, and I get that. 

We were working with more time, though, so that’s how we came to be a little further out. If you’re in Burnham as we were, take it easy today after the drive. Stroll Unity Pond or visit the Field of Dreams. 

Fun fact: No, it’s not that Field of Dreams . You’ll need to travel to Iowa for that. It’s still not bad.

I watched that movie well into adulthood, by the way, and it is creepy and weird as heck. Does anyone else concur?

Want to follow this New England road trip itinerary to the letter? We stayed at this secluded Burnham retreat during our East Coast road trip. You’ll need to drive to anything you need, but that’s the point of seclusion, right? I’d highly recommend this one.

If you planned better (and in advance), you may just want to stay in Bar Harbor. Use the map below for those:

Day 5: Acadia National Park, Maine

We were about 90 minutes outside of the park, so we hit the road early with our pup in tow to make the most of that hike. If you’re visiting with your furry friend, check out my guide to making a similar day trip to Acadia happen. I include dog-friendly trails and where they’re not allowed, too.

Whether you’re traveling with a pup or on your own, Acadia is a hikers’ paradise with some of the best views anywhere in the United States. Don’t miss these trails and attractions if you’re here for all of that:

• Bass Harbor Head Light Station, or more casually known as the Bass Harbor Head Lighthouse, isn’t the most photographed lighthouse in Maine. It’s still worth a stop if you’re early on in your lighthouse exploration. Visit this one on Mount Desert Island.

• If you’re here for the leaves and not the hikes, the Park Loop Road is 27 miles worth of scenic driving through some of the best views in the park. There are all kinds of short loop hikes that start along this path if you’re looking to stretch your legs as you drive.
• Reach Cadillac Mountain with either a steep 3.1-mile ascent to the summit or a scenic drive complete with pullouts along the way. We did the drive up and didn’t feel like we missed out on anything.
• Stroll the Ocean Path Trail to quintessential Acadia attractions like Sand Beach, Otter Cliffs, and Thunder Hole. Thunder Hole sounds more menacing than it is. It’s named for the waves that crash against the rocks here. On ideal days, the spouts can go as high as 40 feet.
• If you’re traveling with a pup as we were, the Wonderland Trail is much less crowded than the trail I just mentioned and just as fun. Make sure your pup can handle rocky areas and a little scrambling if you go that route.

Day 6: Bangor, Maine

Stephen King fans won’t want to miss this one. The town was the home of the horror author for decades until he decided to split his time between his other home in Maine and a Florida home.

You can still visit the mansion’s gates as I did, likely with other fans giggling about the wrought iron accents.

Yes, that’s a red balloon in the photo.

For a full day of fun, check out a few more Bangor highlights:

• Paul Bunyan Statue: This 31-foot-fall statue is here to tell all who visit Bangor that the town was his place of birth. That’s what locals say anyway. He’s very tall, a little bit creepy, and an easy stop while in Bangor.
• Mount Hope Garden Cemetery: If you love a good cemetery, don’t miss the second-oldest garden cemetery in the country. Oh, and it was also a filming location for Pet Sematary . (Did you know that was spelled that way?!)
• Hollywood Casino: If you want to try your luck at some card tables or whatever else people do at casinos, head to one of only two casinos in Maine at the Hollywood Casino Bangor . Can you tell I prefer spending my money elsewhere? I don’t judge you, though.
• Penobscot Narrows Bridge: You’ll need to travel about 30 minutes south of Bangor for this attraction, but if you’re a bridge nerd at all, you’ll want to see this one. Connect to the Fort Knox Historic Site and the Penobscot Narrows Bridge Observatory on the other side.

Day 7: Rockland, Maine

This is peak coastal Maine right here and the part of the state that made me consider Maine as a potential new home for us. Yes, there will be lighthouses and plenty of them. For the best of Rockland, check out these highlights:

• Rockland Harbor Trail: Embrace those maritime vibes with this stroll along Rockland Harbor. If you’re visiting in the fall as I did, expect vibrant foliage on the side that isn’t the waterfront.

• Jess’s Market : If you’re not sure where to get started for delicious seafood in town, start with this fish and lobster shop. Visiting on a chilly day? They’ll likely have chowder for you to slurp up, too.
• Marshall Point Lighthouse: This lighthouse is about a half hour south of Rockland in Port Clyde, but it’s one of the most picturesque scenes you’ll encounter in this part of the country. Oh, and it was also featured in Forrest Gump , so run right over, k?
• Owls Head Lighthouse: This stunner was built in 1825 and has since become one of the most popular lighthouses in MidCoast Maine. It’s a short 10-minute drive to this one from downtown Rockland, so I think I’m cheating even less with this one.
• Rockland Breakwater Lighthouse: If you haven’t navigated breakwater with a dog yet, this is a great place to test out your pup’s mettle. Watch your step — the breakwater is nearly a mile long here! — and head all the way up to the lighthouse for panoramic views at this safe harbor.

We stayed in Owls Head, Rockland’s neighbor, as our overnight in the area. Both are adorable and great places to stay overnight.

If you want to stay in Rockland proper, use the map below for some options:

Days 8-9: Portland, Maine

You’re only a few hours to Portland from here. Portland is Maine’s most populated city, the cultural heart of the state, and my preferred Portland. While you know how much I love coastal Oregon and the other Portland , Maine just hits differently. 

Take some time to enjoy those (hopefully) sunny autumn days in Portland and the best of the Maine city’s attractions: 

• Portland Head Light: This historic lighthouse is in Cape Elizabeth, but that’s just a 15-minute drive from downtown Portland. You’ll drive through South Portland to get to Portland Head Light, one of the state’s most photogenic spots.

• Old Port: Start in this charming historic district and fall in love with Portland just as we did. The Old Port boasts a great dining and live music scene on top of that adorable cobblestone.
• Eastern Promenade: This harbor-side stroll is 2 miles from end to end, but you can do as much as you please. This promenade comes to us courtesy of the same folks who brought us Central Park in New York and the Boston Commons.
• A Piece of the Berlin Wall: There is an actual piece of the Berlin Wall right here in Portland. Find the trio of slabs at Long Wharf, a harbor that’s worth your time with or without a visit to this literal piece of history.
• Bug Light Park: If Portland Head Light didn’t do enough for you, head to Bug Light. This one got its name for its small size, but it’s not the size that matters. It’s how a lighthouse keeper uses their…light? I don’t know. It’s cute.

Once you’re done with the sightseeing, indulge in some of Portland’s best eats. If you haven’t had at least half a dozen lobster rolls yet, grab another at Portland Lobster Company . The outdoor tented bar is a great place to grab a drink and chow down.

Here are a few more food recs as you eat your way through Portland:

• Boone’s Fish House & Oyster Room : Slurp up more oysters with your waterfront dining or opt out as I would with their chowder and delectable mussels. Yes, you’ll want to add more bread.
• Duckfat : If you’re still thinking about the fries you housed on that one trip to Brussels , make a beeline for Duckfat and their Belgian-style frites. They’re double-fried. In duck fat. You’re welcome.
• Eventide Oyster Co. : I’m honestly not the right person to ask about oysters, as I call them the boogers of the sea. Outside of their well-known oyster program, though, this eatery does it up with crab buns, lobster stews, and some bangin’ ceviche. All of that is much more up my alley.
• Terlingua Restaurant & Market : Portland has incredible seafood. If you’re craving some hot meats — get your head out of the gutter — plan to taste some Maine barbecue at this casual eatery. (It’s a blend of Caribbean, Southwest, and Mexican flavors, not an actual state-sanctioned BBQ style.)

Interested in a drink before or after to build that base? Portland’s beer scene is unmatched. Allagash Brewing Company is where you should start.

If you’re planning on crawling to your Portland accommodations, Austin Street Brewery , Rising Tide Brewing Company , and Oxbow Blending & Bottling are all a good time, too.

Stay in Portland for a couple of nights so that you’re able to spend at least a full day sightseeing and another full day eating your way through all of that delectable seafood. We stayed at the La Quinta by Wyndham Portland with our pup in Portland.

We generally love the La Quinta brand when we have our dog along because they don’t slap you with excessive fees and parking is easy. I’d recommend it anyway!

Use the map below for more options in Portland:

Day 10: Portsmouth, New Hampshire

Portsmouth is a lovely place that deserves a day of your time, especially if you’re visiting in the fall when the sun’s still shining and the leaves are crunching. For more on what we did there, visit my guide to this New Hampshire town .

If you don’t want to leave this post just yet, here are the Portsmouth highlights:

• Market Square: This is basically Portsmouth’s beating heart. It’s where you’ll find the bulk of the town’s boutique shopping, cafes, and art galleries. They do it up around Halloween with their decor, too.

• Portsmouth Book & Bar : Their motto is “Eat, drink, read, repeat,” and you can certainly make all of that happen at this wine-coffee-bookstore. Watch their website for upcoming live music, too.
• Prescott Park: Take in the views along the Piscataqua River with a stroll at Prescott Park. This is also where you’d check out the Prescott Park Arts Festival if you weren’t visiting in the fall. (Fall in Portsmouth is still the best, by the way!)
• The Warner House: This is just one of Portsmouth’s historical homes, but it was the one we chose to visit during our own Portsmouth trip. This house is over 300 years old, making it one of the oldest brick structures in New England.
• Memorial Bridge: Want to do something fun? Walk across this bridge. You’ll be in Maine on the other side. Just make sure you don’t time your stroll around the regular bridge lifting.

You’ll need somewhere to stay in or near Portsmouth. We’ve stayed at the  Ale House Inn , a historic property that once housed a brewery.  It was more than a novelty. This was a fun, comfortable stay with possible deals in the off-season.

More Ideas for a New Hampshire Fall Road Trip

Now, you may be wondering where the White Mountains and Mount Washington are in this tour of New England, particularly in the fall. Well, those mountains are thick with peepers in October. You need to book well in advance if you don’t want to spend $400/night on accommodations in and around the White Mountain National Forest.

We just couldn’t do it.

That doesn’t mean you shouldn’t. It’s still firmly on our list, and we plan on returning. Specifically, I imagine myself snapping pics overlooking Crawford Notch State Park and bopping around North Conway on the regular.

Here are a few more items on my New Hampshire bucket list:

• Franconia Notch State Park
• The Conway Scenic Railroad
• Dixville Notch State Park
• Kancamagus Highway
• Lake Winnipesaukee
• Cannon Mountain Aerial Tramway

I know. It’s a lot to return to, and I could basically have myself a New Hampshire fall road trip and still not see it all. While just driving through the state and its surrounding mountainsides was spectacular in the fall, I’m certainly not opposed to doing so in seasons that aren’t at the peak time for New Hampshire.

Days 11-12: Boston, Massachusetts

In just two more hours, you’re in Boston. If you’re flying into New England for less than the length of this itinerary, this is a great hub to choose for some excellent leaf-peeping drives from Boston, especially if you’re short on time. 

As we have so much to see, I’m only dedicating two full days to one of the best cities in Massachusetts , but you’ll certainly want to come back. 

With more time, you’ll be able to tack on a few day trips from Boston. Salem is all kinds of fun if you’re visiting around Halloween time. Want to have yourself a spooktacular time? I have a guide to visiting Salem in the fall .

Cape Cod is perfect for lovers. I don’t know. I just think about all the mayhem those Kennedys got into on the Cape.  For more, check out my post on day trips from Boston .

If you’re staying in Boston proper, you’ll have so much to do to fill your time. If you’ve never done the Freedom Trail, you can spend at least a full day doing that. On top of the historical attractions along the Freedom Trail, don’t miss:

• Boston Common: This is a great place to lounge and people-watch if your legs are tired from the Freedom Trail. It’s also the oldest park in the United States.

• Isabella Stewart Gardner Museum : Visit this art museum for the art, certainly, but stay because its courtyard is one of the loveliest places in the city. You’ll feel like you’re anywhere but Boston and that’s purposeful. This place was modeled after a Venetian palace.
• Museum of Fine Arts, Boston : This museum isn’t just a jewel of Boston’s art scene. It’s well-regarded as one of the best art museums in the United States. It boasts the only permanent exhibition of ancient coins in the U.S. and an impressive Claude Monet collection, among so much more.
• Harvard Square: You’ll have to travel a bit to get to Cambridge, but how can you not visit the home of Harvard University and practice those Good Will Hunting accents you pull out after a good brewery? Start with Harvard Square, the town’s arts and eats center.
• Boston Breweries: Speaking of good breweries, Boston has plenty of them. Trillium Brewing Company , Aeronaut Brewing Co. , and Harpoon Brewery , the local staple, are the top stops I’d recommend if you’re planning to return to the hotel a little tipsy.

We stayed in Lexington on our last visit to Boston, but I’d probably just stay in Boston proper if I was to do it again. The traffic in the city can get intense and if you’re short on time, you’ll want to be in the thick of it all.

Just book well ahead of your travel during fall foliage time, as things can get expensive in Boston.

Use the map below for options in Boston proper:

Day 13: Providence, Rhode Island

Providence is an excellent city to spend the day. For whatever reason, it hasn’t arrived as a popular fall foliage road trip destination, so you’ll compete with fewer leaf peepers while you’re there.  If you’re still not convinced, I have a post on all of the reasons you should make a trip to Providence happen.

Interested in the highlights? While in Providence, don’t miss:

• The First Baptist Church in America :  This is the oldest Baptist church in the United States. Check out the exterior at the very least unless you’d like to time a visit during a worship service.

• Trinity Brewhouse : I had a hard cider here that tasted like apple pie with this sugar rim that caused me to melt into my booth. Yes, I still think about it. I also still think about the incredible mural this place has over the bar. It’s a version of The Last Supper with dead musicians. You’ll want to see it.
• Brown University: Walk the campus or head straight to Thayer Street. This is where both locals and Brown coeds go for casual eats and some of the city’s best ethnic cuisine.
• West Side Diner : This classic diner has been operating out of a diner car on this spot since 1947. It was just known as Poirier’s Diner back then. Order yourself a patty melt and feel yourself go back in time.
• The Museum of Art, Rhode Island School of Design : You’ve probably heard of this one by its shortened name: RISD. The museum’s impressive exhibits touch on a little bit of everything, including fashion. It’s a must-see while in Providence.

If you have more time to explore Rhode Island, don’t miss Newport. It’s very different from Providence, just from a point of fanciness. I put together a guide to its mansions , one of the most popular things to do in Newport if you want an idea of how fancy things get around here.

If you only have time for one Newport mansion, by the way, make it The Breakers. The old Vanderbilt pad is the most popular for a reason.

Providence offers more budget-friendly stays than Newport as you look to book your overnight at this point. I’ve stayed at the Residence Inn Providence Downtown on stays in Providence. What it lacked in charm it made up for with charming prices.

Use the map below for some more options:

Day 14: New Haven, Connecticut

New Haven quickly became one of my favorite New England cities on our New England fall trip itinerary. That one prestigious university adds quite a bit of cultural heft to any visit there, with several of the country’s top museums all in one place. Already into it? I’ve got a New Haven guide . 

At the very least, you’ll want to eat your way through the best New Haven pizza .

Spoiler alert: It was Pepe’s for me. While Pequod’s in Chicago will always hold a special place in my heart, New Haven-style pizza is also quite special. 

If you want the quick ‘n dirty highlights on New Haven, don’t miss:

• Harkness Tower: This is a symbol of the city and a symbol of Yale University. Tours to the top are available during certain times of the year, so check that out if you want the best view of the campus.

• Yale University Art Gallery : See works from van Gogh, Monet, and Rubens without paying a dime to do so. Expect to spend a few hours at this one. It’s also my favorite rainy-day activity in New Haven.
• PEZ Visitor Center : This one is technically in Orange, but it’s close enough that I wouldn’t get upset by another travel blogger sending me outside of the city. It’s a no-brainer whether you’re traveling with kids or just PEZ-loving adults.
• Marjolaine Pastry Shop : Reward yourself for all that learning with some high-end sweets. We visited on a gloomy day, so I had to get myself a decadent hot chocolate. It was a “yes” on the whipped cream, too.
• Yale Center for British Art : Start at the gallery above, but continue with this art museum, the largest collection of British art outside of the U.K. The halls inside are impressive all on their own.

We spent a full week in New Haven because it was one of the more budget-friendly stays in New England during our fall travels. I wouldn’t recommend where we stayed, so you won’t see it here. It was the size of a shoe, not even the full shoe closet.

If you’re lucky enough to be overnighting in New Haven, check out the map below:

With More Time on a New England Road Trip

If you want to stay in New England for a bit longer, I don’t blame you. New Haven is a great base for day trips to other Connecticut fun. Julia Roberts fans won’t want to miss the place that gave us Mystic Pizza just under an hour from New Haven.

Hartford, Connecticut, is another great day trip, particularly if you’re a fan of Mark Twain. It’s home to the Mark Twain House & Museum . Their excellent tours will tell you all about the life of Twain and his family in that house from 1874-1899. 

We booked one of their living history tours. Twain’s former maid, costume and all, told us about all of the gossip she overheard while living in the house with his family. It was very entertaining and very well done.

With more time in Hartford, visit the Harriet Beecher Stowe Center and both capitol buildings. There’s the current Connecticut State Capitol and Connecticut’s Old State House. Both are worth your time.

Art fans won’t want to miss the Wadsworth Atheneum Museum of Art . It has a little bit of everything, whether you’re a fangirl for the Impressionists or were obsessed with ancient Egypt as a kid.

This is where I leave you, a full two weeks after you began your New England fall road trip. We continued traveling south for the winter from here, driving down into Delaware, Maryland, and West Virginia along the way.

You can certainly extend your time at any point during your trip. I could bop around Maine indefinitely, to be honest.

New England Fall Road Trip FAQs

Which new england state has the best fall foliage.

Vermont is the New England state with the best fall foliage. To be honest, if you can’t make it to Vermont, you’ll have vibrant colors in any of the New England states. That includes Vermont, Connecticut, Rhode Island, Massachusetts, New Hampshire, and Maine.

What is the best time to see fall foliage in New England?

The best time to see fall foliage in New England is when the leaves start changing colors. This sounds vague on purpose. The timing changes somewhat from year to year. Mid-September through the end of October is usually the best time to see New England fall colors.

The New England fall road trip itinerary you read about here happened around the start of October into the middle of the month, and the colors were spectacular.

Is New England expensive to visit?

New England can be expensive to visit, especially if you want to live off of lobster rolls for the duration of your visit. 

Visiting in the fall in particular on a New England itinerary can really test your budgeting skills. It can cost a pretty penny to stay in the most well-known towns around New England if you don’t plan far in advance. 

We booked our accommodations a few months ahead of our own trip, and it really wasn’t enough time. The highlight, though, was experiencing the smaller, less popular stops along the way.

Is a New England road trip worth it?

A New England road trip is absolutely worth it. New England is already one of the most beautiful regions in the United States. Add the vibrant hues of fall and it’s all almost overwhelming.

It’s what made me seriously consider moving to New England until I started thinking about winters , too.

Ready for Your New England Autumn Road Trip?

Your Flight:  I use a variety of tools to find cheap airfare, but if you’re looking to book during a particular period of time, especially during busy times (e.g. autumn in New England), you should use  Skyscanner . It’s a great tool for when you’re more flexible, too, as it allows you to compare travel based on length of travel, departure date, etc.

Scroll up for logistics around East Coast fall road trip travel and good starting points for a New England fall foliage road trip.

Adventurous folks may love subscribing to  Going , formerly Scott’s Cheap Flights. You’ll get all kinds of deals in your inbox throughout the year, including those targeting New England road trips.

Your Accommodations:  I usually use  Booking.com  and  Hotels.com  for our hotel needs. Both offer loyalty programs, and now offer listings that are more of the home or condo rental variety, which is great. Vrbo is my preferred Airbnb alternative. Scroll up for my top picks on accommodations throughout your New England fall road trip.

Seeking even more wallet-friendly accommodations? Try  Hostelworld . Their picks are heavily vetted and reviewed to offer you a safe experience on a budget.

Etc.:  For general travel goodies, visit my  Favorite Things  page. For more information on planning your travel, visit my  Travel Tools  page.

Love this New England fall itinerary? Pin me!

Interested in more travel over this way? Check out these posts:

• Marvel at A Christmas Story  House in Cleveland
• Stay at These Cabin Escapes in North Carolina
• Visit Virginia’s Underrated Natural Bridge State Park
• Plan a Southern Road Trip While You’re Here
• How to Spend a Weekend in Asheville, NC

Ready to see more?

Subscribe to my biweekly newsletter for hot travel tips I come across, weird stories you won’t see elsewhere and perhaps lifelong friendship.

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Agnes Groonwald

Unforgettable New England road trip

• Post last modified: March 18, 2024

Planning a road trip through New England ? Get to the heart of the United States ‘ most idyllic corner with this ultimate itinerary, where soothing nature, delightful towns and proud tradition abound. Buckle up — here are all the gems you don’t want to miss.

Disclosure: All listings are independently selected. If you buy something through our links, we may earn an affiliate commission. Learn more ›

New England route

• Start: Boston
• North Conway
• North Adams
• Stockbridge
• Finish: Boston

Begin with a salty trip up along New England’s coast, where Portland, Camden and Acadia NP are highlights. While Interstate 95 is usually quicker, consider sticking to the parallel, more scenic Route 1.

Then, the character of the itinerary changes dramatically. Head west to see the White Mountains, Green Mountains and Berkshires, with the lofty scenery peaking along the iconic Kancamagus Highway.

Back on the coast, explore Mystic, Newport and Cape Cod. Home to Cape Cod National Seashore, Cape Cod provides some of America’s best beaches, making for the perfect finish to your epic drive.

Isn’t Boston the optimal starting point for you? Feel free to start the loop at the location that suits you best.

• Total distance: 1,213 mi / 1,952 km
• Total driving time: 25 h

1. Boston, MA

Massachusetts ‘ largest city, Boston is certainly a convenient place to begin a Northeast road trip. There’s the well-connected Logan Airport and an array of rental car companies to choose from.

But — most of all — Boston is a fun city to explore before you get deeper into the New England itinerary.

If one thing to do in Boston is mandatory, it’s the Freedom Trail . Walking the 2.5-mile (4 km) path, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a memorable experience before heading north — baseball fan or not.

More info: Where to stay in Boston

2. Portland, ME

• Driving distance:  112 mi / 180 km
• Driving time:  2 h

On Maine’s southern coast, Portland offers a lot for anyone looking for a good time.

In particular, the historic Old Port — characterized by cobblestone streets, red-brick buildings, quaint wharves and fishing piers — is the crown jewel. While its facades remind you of past glory days, the district is a modern-day gold mine with eclectic boutiques, watering holes and restaurants.

Capturing at least one of the many lighthouses in the Portland area is also a must, and especially one stands out: Portland Head Light was completed in 1791, making it Maine’s oldest lighthouse.

3. Camden, ME

• Driving distance:  81 mi / 130 km
• Driving time:  1 h 45 min

Countless scenic towns hug Route 1. Camden may be the most picturesque of them all.

Picture a small town lacing an Atlantic cove (Penobscot Bay) with steep slopes (Camden Hills). If you’re short on time, stretch your legs while you browse the stores on the timeless Main Street or sit down in the Camden Amphitheater, a small oasis facing the harbor.

With more time, hike into the rising Camden Hills State Park. But if you don’t want to work for it, you can also drive up to the top of Mount Battie, brilliantly capturing the scenery.

4. Acadia NP, ME

• Driving distance:  77 mi / 124 km

Welcome to the only national park in New England, Acadia. Calling Mount Desert Island home, it encompasses some of the Atlantic’s most untamed coastline — this is one of the most beautiful places in the US .

Although you find awe-inspiring nature all over the island, the eastern half of Mount Desert Island holds most of the park’s big-ticket spots.

An unrivaled eastern highlight is Cadillac Mountain. The views of Acadia are just spectacular from Cadillac Mountain’s summit, both the tallest point of the park and the USA’s eastern seaboard.

Cadillac Mountain peaks at sunrise and sunset but is a beautiful experience throughout the day.

On Mount Desert Island’s quieter western half, another photogenic spot not to miss is Bass Harbor Head Lighthouse. Built in 1858 on the island’s southern tip, it’s not quite as old as Portland Head Light — but no less pretty.

More info: Where to stay near Acadia NP

5. North Conway, NH (White Mountains)

• Driving distance:  212 mi / 341 km
• Driving time:  4 h 15 min

New Hampshire ‘s White Mountains region is filled with great things to do, boasting both stunning natural beauty and cozy towns to relax in.

A shining example of the latter, North Conway is the perfect White Mountains gateway when you come from the east. From here, you effortlessly reach many highlights in the dense White Mountain National Forest.

Within a few miles, Diana’s Baths Cascade — a series of waterfalls dropping 75 feet (23 m) — is a spellbinding place. Another nearby stop is Cathedral Ledge Lookout, offering White Mountains vistas destined for Instagram fame.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway — one of New England’s most scenic drives — is a jaw-dropping experience. As it runs from Conway to Lincoln, it also takes you right to your next base on the itinerary.

6. Lincoln, NH (White Mountains)

• Driving distance:  41 mi / 66 km
• Driving time:  1 h

Ready for more gorgeous terrain? At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest.

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess first had trouble convincing her family about the discovery. It just sounded too magical to be true — but the rest is history.

Today, the Flume is a highlight in Franconia Notch State Park. You find a good variety of hiking trails in Franconia, letting you explore the White Mountains and its dense forests, stunning lakes and majestic peaks further.

7. Stowe, VT (Green Mountains)

• Driving distance:  85 mi / 137 km

A Vermont village with a postcard-worthy downtown area, Stowe sits at the foot of the Green Mountains.

Just strolling down Main Street in Stowe is an appreciated thing to do. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far from fresh air and beautiful views. Stowe Recreation Path provides a convenient way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. Be careful so you don’t get a brain freeze at the original Ben & Jerry’s ice cream factory in Waterbury.

Extra stop: Consider stopping in Burlington, VT, a fun city on the shore of Lake Champlain. Because it’s just 36 miles (58 km) between Stowe and Burlington, you can easily include both on your New England itinerary.

8. North Adams, MA (The Berkshires)

• Driving distance:  159 mi / 256 km
• Driving time:  3 h 15 min

It’s the rolling hills and captivating culture that define The Berkshires region. Marking its northern end, where Vermont meets Massachusetts, North Adams is a great place to start exploring.

Be inspired by evocative galleries and performances at the Massachusetts Museum of Contemporary Art, set on the Hoosic River in downtown North Adams.

Or, simply cruise onwards, letting the peaceful landscape wash over you. North Adams sits along the Mohawk Trail, one of New England’s most scenic drives, finishing in nearby Williamstown.

9. Stockbridge, MA (The Berkshires)

• Driving distance:  35 mi / 56 km

America’s favorite illustrator, Norman Rockwell called Stockbridge home for 25 years. Here, with hundreds of original works, the Norman Rockwell Museum honors and showcases his legacy.

Before Rockwell, the writer Edith Wharton lived in the Berkshires, too. Visit her historic Lenox residence, the expansive Mount Home (maybe on your way from North Adams to Stockbridge), to learn and absorb the idyllic setting.

These are cultural treasures, but don’t forget that what makes the Berkshires outstanding is the mix of culture and nature.

For hiking, a beautiful spot is October Mountain State Forest . At roughly 16,500 acres, it’s Massachusetts’ largest state forest, offering both easy and strenuous trails.

More info: Where to stay in The Berkshires

10. Mystic, CT

• Driving distance:  127 mi / 204 km
• Driving time:  2 h 15 min

On the Connecticut coast, the village of Mystic peacefully sits. Get ready to discover its proud history as a waterside community and center for shipbuilding.

By the Mystic River, Mystic Seaport Museum is one of the USA’s leading maritime museums, preserving an array of seafaring artifacts. Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws.

Compact Historic Downtown Mystic has you covered for authentic shopping, diverse eateries and charming waterfront views. Especially pay attention to the Mystic River Bascule Bridge, a still-in-use drawbridge — nowadays a rare sight.

Extra stop: An alternative to Mystic or an additional stop on the itinerary is New Haven, CT, the home to the famous Yale University.

11. Newport, RI

• Driving distance:  48 mi / 77 km

The shore of Rhode Island is an essential ingredient on your New England road trip itinerary. On Aquidneck Island, Newport is an old colonial city with attractions covering a wide spectrum.

Walking the renowned Newport Cliff Walk, 3.5 miles (5.6 km) long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and fresh salty air.

As a bonus, eye-popping mansions frame the trail.

For the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are also impressive.

More info: Accommodation in Newport, RI

12. Cape Cod, MA

• Driving distance:  120 mi / 193 km
• Driving time:  2 h 30 min

These 120 miles (193 km) take you all the way to the northern tip of Cape Cod , a peninsula separated from the mainland by the Cape Cod Canal since 1914. Be sure to make plenty of stops along the way.

Cape Cod Rail Trail, excellent for walking or biking, presents a healthy way to sightsee. Paved and extending for 25 miles (40 km) from South Yarmouth to Wellfleet, it follows the 19th-century rail lines that used to carry tourists to Cape Cod.

At the trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly never-ending beach — seals thrive in the waters here — or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach, as far north as you get, is a phenomenal beach with huge sand dunes. On a sunny day, you might ask yourself: Is this Massachusetts or Florida?

More info: Best areas in Cape Cod

13. Boston, MA

• Driving distance:  116 mi / 187 km

It’s time to round off your unforgettable New England road trip. The last leg is the drive back to where the adventure started, Boston. From the isolated Provincetown, it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself elsewhere on Cape Cod.

Where to stay when you road trip through New England

New England takes pride in its atmospheric, often historic inns. Consider making your road trip even better by booking one of our favorite places to stay on Cape Cod.

Appreciate the English Country style at the Old Harbor Inn , a luxurious bed and breakfast set in Chatham. Each of the twelve rooms is unique and the location spot-on for day trips across Cape Cod.

Or, stretch your budget by staying at the Breakwater Hotel , slightly outside Provincetown, at Cape Cod’s northern tip. Drive 5 minutes or walk 30 minutes to get to Provincetown’s heart.

New England itineraries with days

For the full New England road trip, we recommend allowing at least 3 weeks. If you have less time, it’s a good idea to break up the itinerary to focus on your favorite parts.

Ultimate itinerary (3 weeks)

• Day 1-3: Boston (2 nights)
• Day 3-5: Portland (2 nights)
• Day 5-8: Acadia NP (3 nights)
• Day 8-10: North Conway (2 nights)
• Day 10-12: Lincoln (2 nights)
• Day 12-14: Stowe (2 nights)
• Day 14-15: The Berkshires (1 night)
• Day 15-16: Mystic (1 night)
• Day 16-18: Newport (2 nights)
• Day 18-21: Cape Cod (3 nights)

2 week road trip (Atlantic coast)

• Day 1-2: Mystic (1 night)
• Day 2-4: Newport (2 nights)
• Day 4-7: Cape Cod (3 nights)
• Day 7-9: Boston (2 nights)
• Day 9-11: Portland (2 nights)
• Day 11-14: Acadia NP (3 nights)

7 day road trip (Mountain trip)

• Day 1-4: White Mountains (3 nights)
• Day 4-6: Green Mountains (2 nights)
• Day 6-7: The Berkshires (1 night)

New England road trip FAQ

This ultimate New England road trip is 1,213 miles (1,952 km) long, taking 25 hours excluding the time you need for the stops along the way.

The journey includes six states: Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

The main stops on the itinerary are Boston, Portland, Acadia NP, White Mountains, Green Mountains, The Berkshires, Mystic, Newport and Cape Cod.

For the full loop, we recommend allowing 3 weeks or more. But you can break the itinerary up and enjoy a shorter journey, too, for example, focusing on the coast or the mountains.

With 7 days, it’s as good idea to concentrate on a certain area. To see both a lively city and New England’s timeless coastal environment, a popular combo is Boston and Cape Cod.

More New England guides

• Cape Cod vacation guide
• Where to stay in Cape Cod
• Lodging near Acadia NP
• New England bucket list

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Travel Better, Cheaper, Longer

Road-Tripping New England: My Suggested Itinerary

I’ve said it before and I’ll say it again: The United States is made for road trips . With its bustling cities, rugged national parks, and delicious eats, the sheer size and diversity of this country never cease to amaze me.

I’ve road-tripped the USA five times, spending a cumulative year exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.

One region in particular that I love to drive around is New England.

Having grown up in Boston and gone to college in Western Massachusetts, I’ve spent a lot of my life in this part of the country. I’ve also road tripped around the region.

During a recent summer, I explored parts of Maine , Cape Cod, and upstate New York that I had never seen before.

And yeah, I’m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.

If you’re thinking of visiting, here’s a suggested road trip around New England to help you get a feel for the region:

Table of Contents

Days 1-3: Boston, MA

Days 4-5: portland, me, days 6-8: bar harbor, me, day 9: bangor, me, days 10-12: moosehead lake, me, days 13-14: mount washington, nh, days 15-17: burlington, vt, days 18-19: green mountain national forest, vt, days 20-22: the berkshires, ma, day 23: amherst, ma, day 24: back to boston, bonus destination: cape cod, ma.

These are some of my favorite things to do in Boston:

• Walk the Freedom Trail – This 2.5-mile (4km) route takes you through colonial Boston. Starting in the Boston Common and winding past Faneuil Hall, the Old State House, and Bunker Hill, this historical walk teaches you about life in colonial and revolutionary times. If you’d prefer a guided tour, Boston History Company runs daily tours for $31 USD that offer excellent insight into the area’s important past.
• See the Museum of Fine Arts – This museum has over 450,000 pieces of fine art, from the pre-Columbian era to Italian Impressionism. It’s one of the best collections in the country. Admission is $27 USD.
• Visit Bunker Hill Monument – The Battle of Bunker Hill in 1775 was one of the first major clashes of the Revolutionary War. While the redcoats won, the Americans wore British forces down more than was expected. The monument stands 221 feet tall; you can climb to the top to enjoy the view (it’s the best view of Boston).
• Lounge in Boston Common – This is the oldest city park in the US, dating to 1634. It was once used as communal pasture land by Puritan settlers (they also executed some “witches” here as well). Today, it’s a great place to relax, people-watch, and picnic.
• Visit Harvard – Harvard University is the first and oldest university in the country (founded in 1636, far predating the United States). The campus offers free one-hour tours through the grounds and buildings. Afterward, grab a coffee and people-watch in the alternative and artsy Harvard Square.
• Catch a game at Fenway Park – This is one of the oldest baseball parks in the country (it opened in 1912). Bostonians are die-hard Sox fans, so even if you don’t like baseball, go for the cultural experience. Tickets start around $29 USD for standing room or bleacher seats, and $39 USD for the grandstand. Guided tours of the stadium are offered year-round as well. There are various tour options, but the standard guided tour lasts 90 minutes and costs $25 USD per person.

For more suggestions on what to do in the city (and there’s plenty), check out my free guide to Boston .

Where to Stay

• HI Boston – This is my favorite hostel in the city. It’s clean, spacious, and social, and the staff are super friendly and helpful.

For more suggestions, here is my list of the best places to stay in Boston .  

• Visit Peaks Island – This small island is home to around a thousand people. Located just 20 minutes off the coast, it’s a laid-back place to eat, lounge, and check out the quaint shops. There’s also a small World War II museum here, as well as a neat umbrella cover museum (it’s more interesting than it sounds!).
• Try a Holy Donut – Holy Donuts are made from Maine potatoes (which sounds weird, but they are incredibly tasty), so they are at least somewhat healthier than your standard donut. There’s always a line, so try to get there early!
• See the lighthouses – There are several historic lighthouses worth seeing nearby, including the Portland Breakwater (which was designed to look like a Greek monument), Spring Point Ledge (which was built in 1897 and is open for tours on weekends), and Portland Head Light (which was built in 1791).
• Wander Victoria Mansion – This ornate mansion-turned-museum, built in 1860 and declared a National Historic Landmark in 1971, boasts a brownstone exterior and elaborate interior furnishings. It’s incredibly lavish, shedding light on what life was like for the well-to-do in the late 19th century. Admission is $19.25 USD.

While you’re in Portland, be sure to check out some of the city’s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.

• Black Elephant Hostel – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping.

Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.

Here are some things to see and do in and near Bar Harbor:

• Explore Acadia National Park – This gorgeous national park encompasses forests, lakes, and mountains, and covers a large swath of the Atlantic coastline. It’s incredibly popular in the summer for hiking, biking, camping, kayaking, and more. You could easily spend a couple of days just exploring the park. A 7-day vehicle pass is $35 USD and camping starts at $22 USD per night.
• Visit Abbe Museum – This museum showcases the area’s indigenous history and culture. It’s very informative and sheds important light on a history often overlooked. It’s part of the Smithsonian, so you know it’s going to be good! Admission is $10 USD.

Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie’s (delicious food all around).

• Bar Harbor Manor – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace.

My favorite places to eat are Fiddleheads (delicious food all around) and Judy’s (best diner breakfast). For a drink, head to Mason’s Brewing.

Where to Stay Bangor is a small town, so you’ll want to compare prices on Booking.com and Airbnb to see what best suits your budget.  

Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer.

For dinner or drinks, head to the Stress Free Moose Pub in Greenville.

• Leisure Life – This accommodation is basic, but it’s in a great location (in Greenville), and the staff are super helpful.

Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).

Where to Stay You can stay in nearby Gorham or Littleton. Check Booking.com and Airbnb to see what best suits your budget.  

Some of my favorite things to do here are the following:

• Wander Church Street – This pedestrian-only thoroughfare is the heart of the city. Café-hop, browse the bookstores and other shops, and take in the slow pace of life.
• Get out on the water – Spend some time out on the water and soak up the sun. Boat rentals, cruises, paddle boarding, kayaking — you can do it all here. There are also several beaches you can lounge on, with North Beach being the most popular.
• Visit Ben & Jerry’s – This is where the global ice cream brand originated. If you have more time, you can visit the nearby factory in Waterbury and see the “ice cream graveyard,” where Ben & Jerry’s commemorates its obsolete flavors.
• Indulge in craft beer – Burlington is a craft beer mecca, home to over a dozen breweries. Go bar- or brewery-hopping to taste the best the city has to offer. Local favorites include Foam Brewers, Zero Gravity, Fiddlehead Brewing Company, and the Burlington Beer Company.

Where to Stay There are no hostels here, so compare prices on Booking.com and Airbnb to see what best suits your budget.  

Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.

Since it’s a national forest, camping here is free (unless signs advise otherwise).  

Here are some things to see and do:

• Hike Mount Greylock – Standing 3,491 feet tall and located in a state park encompassing over 12,000 acres, Mount Greylock is the highest peak in Massachusetts. There are several trails that lead to the summit (including a portion of the Appalachian Trail). The hike takes around 90 minutes, and the views from the top are absolutely breathtaking — you can see for miles!
• Visit the Norman Rockwell Museum – Norman Rockwell, the prolific American painter and illustrator, spent much of his life in Stockbridge. A museum was established there to showcase his life and works, highlighting the evolution and impact of his art. Admission is $20 USD.
• Explore Natural Bridge State Park – Located in North Adams, this park is home to a natural bridge of white marble (which is over 550 million years old) as well as an old marble quarry. There’s an easy trail around the bridge and quarry, and plenty of relaxing fields and meadows to picnic in. Parking is $20 USD for out-of-state residents.

Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson’s life. There are often events and poetry readings here, so check the website to see what’s on during your visit. Guided tours last 60 minutes and cost $16 USD.

As for food, Antonio’s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I’m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.

It’s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston!  

Here are some things to see and do during your stay:

• Go whale watching – From April to October, you can see finback, minke, and humpback whales, as well as dolphins and seals. Tours cost around $67 USD.
• Hike or bike the National Seashore – Created in 1961 by JFK, this park spans over 43,000 acres. There are 11 hiking trails, as well as half a dozen cycling trials. All of them are well marked so it’s an easy way to stretch your legs and take in the beautiful landscape.
• Visit some lighthouses – There are dozens of picturesque lighthouses around Cape Cod, some of which are open to the public. Don’t miss Nauset, Nobska, and Highland lighthouses.

New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I’m proud to have grown up in this region and encourage you to explore my backyard!

Book Your Trip to the United States: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe, so you always know no stone is being left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as it has the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it, as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those 70 and over)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road, and I’m sure they will do the same for you.

Need an Affordable RV for Your Road Trip? RVshare lets you rent RVs from private individuals all around the country, saving you tons of money in the process. It’s like Airbnb for RVs.

Want More Information on the United States? Be sure to visit our robust destination guide on the USA for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  November 8, 2022

The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options!) 2024

Having traveled through the entire New England region for 15+ years, I’ve been able to get a strong understanding on the best things to do, and I’m so thrilled that I’ve finally developed my ultimate 7 Day New England Itinerary to share with you!

A 7-day itinerary to tour New England has been one of my most requested topics, and I totally understand why. It’s so hard to look at a region comprised of 6 gorgeous states, and try to figure out what’s worth your time, and what you can leave out. Well, good news – I’m taking the guess work out for you. In all my years of traveling through this region, I’ve cherry-picked what I think is the best route to take to plan the perfect road trip in 7 days.

While I think everything is pretty much worth your time in New England (I’m a bit biased!), this itinerary focuses on the best of the best, and also takes into consideration efficiency so you have as much time as possible to also enjoy your destinations.

This itinerary is also geared toward those who are visiting New England for the first time. With that, let’s get into it, shall we?

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

How Many Days Do You Need In New England?

You can easily spend anywhere from a few days to a month in New England, so this entirely depends on how much time you really have to dedicate to your trip. This post will prove that you can easily see some of the best things in this region with my 7 Day New England road trip itinerary.

But, that said, more is always more when it comes to time to travel, right? 😉 So of course, you can easily turn this itinerary into a 10-day adventure, or even two weeks. Under my 10 Day New England road trip itinerary option later in the post, you’ll see that I’ve made notes on side excursions where you can easily add in a day or two to extend your trip even further.

And of course, you can definitely see some of the best places in just 5 days, and I’ve included a 5-Day option at the very end for those who don’t have as much time (and don’t worry, it’s still pretty great!).

My motto is always, “Even if I just have one day, it’s better than not going at all,” so whatever time you have for your trip with definitely be worth it. I’m excited to cheer you on as you plan your trip 😊

Where To Start A 7 Day New England Road Trip Itinerary?

For any road trip through this region, Boston is the best place to start, especially if you’re flying in. Boston Logan International Airport typically offers the cheapest flights to this area, and is also a worthy destination to explore on its own.

Not only that, this city also incredibly convenient to most places in New England, and is centrally-located in the region, and therefore, is just the easiest starting point. For that reason, pretty much all of my itineraries on this website start in Boston because after years of experience, I’ve found this to be the absolute best option.

If you’re not flying in, however, and already live in this area, or are driving in from nearby, Boston is still a great starting point ( especially if you’ve never been!). But you can definitely adjust this itinerary to start from anywhere in New England that best suits your needs.

The only time I would suggest using a place like Portland, Maine as your starting point if if you plan to really only explore the northern areas of New England, like the rest of Maine or New Hampshire. But even in that case, Boston is still just as convenient, so it will then simply depend on personal preference at that point.

7 Day New England Road Trip Overview

Day 1: Boston – New England’s biggest and most exciting city!

Day 2: Woodstock – Vermont’s most beautiful town.

Day 2 Alternative Option : Skip Woodstock, and stay an extra day in Boston, with a day trip to Salem if you’d like.

Day 3: The White Mountains in New Hampshire – Home to breathtaking mountain views, and New England’s highest peak.

Days 4-5: Bar Harbor and Acadia National Park – One of the most charming coastal towns in New England, and the spectacular views in the park make this destination worthy of two nights.

Day 6: Drive to Portland, Maine , with optional stops along the way.

Day 6 Alternative Option : Stay the night in a smaller coastal town if that’s more your speed!

Day 7: Head back to Boston , with some great stops along the way.

Notes About This Itinerary

→ For some stops along this route, I also suggest other options to really help you create the ultimate road trip for you based on your preferences. So keep an eye out for those, and get ready to take some notes!

→ This 7 Day New England road trip itinerary also follows a true road trip style , meaning you’ll be in a different town each night of your stay (with one exception, which is Bar Harbor). You can certainly tweak that to your liking if you prefer to stay in one place for two or more nights – do what feels right for you.

→ Lastly, this itinerary was intended to show you around all the different landscapes New England has to offer, so I wanted to include a mix of urban, countryside, mountains and coastal to show you the very best of it all. I also focused on locations that are largely perfect to visit year-round, so seasonality was not factored in.

Day 1: Boston

Boston is one of my all-time favorite cities, and as mentioned, it’s the absolute best place to start your road trip – especially if you’re flying in. I love that it feels like an exciting city, but is also incredibly charming, historic and packed with character. There’s just something very cozy about it, and it’s most definitely worth spending a day exploring during your 7 day New England road trip.

An alternative option, depending on how tired you’ll be once you arrive, is to tack Boston on at the very end. In this case, you’ll want to immediately depart for Woodstock once you arrive, and then spend your last day in Boston (but follow this itinerary for everything else in order).

Here are some awesome things to consider doing on your day in Boston:

• Walk the Freedom Trail: this group tour is an excellent choice!
• Meander through my two favorite neighborhoods: Beacon Hill & the North End.
• Stroll along the waterfront areas – the Charles Esplanade is especially beautiful.
• Walk through the Public Gardens – the bridge is such a great spot for gorgeous photos.
• Eat, eat, and then eat some more. The culinary scene in Boston is incredible, and seafood here is a specialty.
• In fact, take a food tour for the inside scoop on all the best places: here are my favorite food tours in Boston .
• Grab some cannoli at Mike’s Pastry.

Hotel suggestions in Boston:

Splurge: Boston Harbor Hotel . A 5-star waterfront hotel that’s more than worth the splurge to kick start your amazing road trip through New England. The location is also convenient to a lot of attractions.

Moderate: Revere Hotel Boston Common . I stay here a lot when I visit Boston. It’s a great location that’s walkable to a lot.

Budget: HI Boston Hostel . Boston is typically an expensive city to visit unless you’re coming in the winter, and this hostel is a great option to save some money during your stay. It also has an awesome location.

Day 2: Woodstock, Vermont (2h 15m From Boston)

Why Woodstock Next? No trip to New England is complete without a stop in a charming Vermont town, and Woodstock is the best of the best when it comes to idyllic scenery and character. It’s also home to “Vermont’s most beautiful address,” which I’ll tell you about under the suggestions on where to stay.

Woodstock has a wonderful town center, where you’ll find independent shops, cafés, and restaurants, covered bridges, farms, and it’s also surrounded by beautiful rural scenery once you drive outside of town. It’s the perfect option for this itinerary if you’re hoping to get a glimpse of Vermont.

Here are some awesome things to do in Woodstock, VT:

• Meander through the most adorable village where all the shops and restaurants are. This part of town is entirely walkable, so park and enjoy!
• Visit the three covered bridges: Middle, Taftsville and Lincoln.
• Explore Billings Farm & Museum.
• Taste local maple syrups and cheeses at Sugarbush Farms.
• Take a drive to Farmhouse Pottery, just outside of the town center, which is now a famous ceramics shop – they have a studio on-site where you can watch artisans at work, or you can book a pottery session with them!

Psst! I have an entire post all about the best things to do in Woodstock, VT , if you’d like more ideas and info 😉

Where to stay in Woodstock, VT :

Luxury option : Woodstock Inn & Resort (Vermont’s most beautiful address!). It’s a splurge, but located right in town, and the perfect way to treat yourself for a 1 night stay.

Moderate: 506 On The River Inn . Very beautiful hotel that’s right on the river and feels cozy.

Budget : The Vesper . A cute little B&B with modern rooms, great prices, and walkable to the village.

Insider Tip s: Woodstock tends to be an expensive place to visit, so if you’re on a budget, the nearby town of Quechee is a great alternative, and is only about 15 minutes from Woodstock. Quechee is also very cute and I love visiting both towns when I’m in the area.

Also, if you visit in the fall during foliage, or your stay happens to be on a weekend, some of these hotels may have a 2-night minimum stay requirement, so keep that in mind.

Alternative Option: If you would prefer to spend 2 nights in Boston and skip Woodstock, you can most definitely do that. Boston is a great place for day trips to other nearby areas, including Provincetown on Cape Cod, as well as Salem. A ferry will take you from Boston to Provincetown, and to Salem, so you still won’t need to pick-up your rental car right away if you choose this option. These ferry options are seasonal, so plan accordingly.

→ Click here to check out ferries from Boston to Provincetown

→ Click here to check out ferries from Boston to Salem

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: The White Mountains, New Hampshire (1h 30m From Woodstock)

Why White Mountains Next? They’re on the way to Acadia National Park (which is the next stop!), and they’re very worth your time ( especially if you’re traveling in the fall season). The White Mountains are home to a great mix of cute towns, epic mountain views, and amazing parks or hiking and scenic drives.

While the White Mountains doesn’t necessarily offer that New England charm you’re probably expecting, I still think this region is worth visiting on your way to Acadia for the reasons mentioned above. The drives through the White Mountains National Forest, and Crawford Notch State Park is so beautiful, and offer such a well-rounded perspective of New England’s beauty, when you combine this region with all the other coastal stops on the rest of this itinerary 😉

Here are some awesome things to do in the White Mountains:

• Explore Franconia Notch State Park , and with 1 day, I suggest prioritizing Flume Gorge, which is perfect for all ages, and one of the most popular attractions in the entire state that’s worth your time.
• If you’re looking for a fun hike, the Artist Bluff Trail offers incredible views of Echo Lake.
• Ride the Cannon Mountain Aerial Tramway to the mountain’s summit for awesome views.
• Explore The Basin, which is very close to Flume Gorge, and is very quick and easy.

Where to stay in the White Mountains? I highly suggest Littleton . It’s a charming little town with awesome shops and restaurants (it’s often regarded as having one of the best Main Streets in the U.S.!), and it’s also very close to some of the top must-see things from my list above, making it super convenient and efficient for 1 day.

However, I have an entire detailed post on where to stay in the White Mountains , if you’re looking for more of a breakdown of the towns, and my hotel suggestions.

Hotel suggestions in Littleton :

Thayers Inn : Located right on Main Street in the heart of downtown, and very cozy. Keep in mind that this is a historic hotel, so they’re not able to make a lot of modern updates, so it’s not for everyone – but I really enjoyed my stay here and appreciated how it felt like I was stepping back in time!

Hampton Inn : A nice option that’s on the commercial side of town, but very close to the highway to get around quicker.

Pro Tip: You’ll drive right past Hanover, NH on your way from Woodstock, which is home to Dartmouth College, and is a really adorable little town to stop in for lunch, or to take a driving break. Right in the same area is Norwich, VT, which is home to the King Arthur Baking Company campus , and is a really fun spot to pick up some baked goods (especially breads and pastries!) and also have lunch outside on their lawn.

Here are some posts you may find helpful while you plan your time in the White Mountains:

• Things To Do In Franconia, NH
• Things To Do In Littleton, NH
• Things To Do In Lincoln, NH

Days 4-5: Acadia National Park & Bar Harbor (4h 30m From The White Mountains)

Why Acadia National Park & Bar Harbor Next? Acadia is one of the most incredible and iconic destinations in the Northeast, and definitely one of the best places to visit in New England . Even though it’s pretty far north, it’s so worth it for the stunning views. I’ve budgeted two nights here because your drive from the White Mountains to Acadia is a bit longer, and because Acadia just warrants extra time.

Also, Bar Harbor, I think, it’s such a quintessential coastal New England town filled with character. The town is small, and very walkable, and you’ll get some nice views of the bay and harbor just by walking along the town’s waterfront.

There’s also opportunities for boat tours from town, great restaurants to choose from, and of course, quick access to Acadia!

Here are some awesome things to do in Acadia National Park for a short trip:

→ Walk Ocean Path , which connects Sand Beach to the Otter Cliffs. This is the perfect scenic walk to tackle with a short amount of time because it’s easy, and offers some of the best and most iconic views of the coastline.

→ Thunder Hole is along Ocean Path, so you’ll pass right by it if you walk this trail. If you’re there on a windy day, the waves will crash so loudly that it sounds like thunder. Otherwise, it’s just a scenic overlook that’s still worth a stop.

→ If you’d like to tackle a hike, a nice one for a quick visit to the park is Great Head . This starts at Sand Beach, and is pretty easy (with some rock scrambling at the beginning), but offers incredible views along the way). After this, you can walk back across Sand Beach and do the Ocean Path for the perfect day in Acadia.

→ Lunch at the Jordan Pond Restaurant is also really fun, and a more relaxing way to spend some of your time in the park. It’s open seasonally only, so plan accordingly, and is famous for their popovers, and incredible views of the famous Bubble Rocks.

→ Sunrise at Cadillac Mountain is one of the most popular things to do, and definitely worth your time! This location is one of the first places in the U.S. to watch the sunrise, and it’s the actually first sunrise spot between October 7 through mid-March. This is another great reason to spend two nights here. Note : Reservations are now required when taking the auto road to Cadillac Mountain’s summit mid-May through October . Click here for more info!

→ Cover more ground by renting E-bikes to explore the park!

→ Click here for more info on renting E-bikes for your trip to Acadia

Psst! I have a few posts on Acadia that you may find helpful, including:

• My Perfect Acadia National Park Itinerary
• The Best Time To Visit Acadia National Park
• Visiting Bar Harbor & Acadia National Park In The Winter

Where to stay while visiting Acadia National Park? Bar Harbor! This lovely little coastal town is the gateway to Acadia, and where most people stay when exploring the park. This is another reason why I’ve given you two days because Bar Harbor is also a worthy town to explore on its town.

Hotel Suggestions in Bar Harbor :

Bar Harbor Inn & Spa : Located right on the waterfront in town, it’s a great place to stay for walkability to town, and if you’re looking for the best amenities and a nicer place to stay.

Bar Harbor Villager Motel : An awesome motel in the center of Bar Harbor’s village, with spacious and updated rooms, and walkable to everywhere in town. I like to stay here when I plan to spend most of my time hiking in the park, and just need a cozy place to crash at night.

Pro Tip : When driving from Littleton to Acadia, I suggest driving to Lincoln, NH first, and then taking Route 112 to Conway, which is the famous Kancamagus Scenic Highway. This drive takes you through the heart of the White Mountains with some really nice overlooks to stop at, and only adds 30 extra minutes to your drive (plus extra time for any stops you make).

Pro Tip : The Kancamagus Scenic Highway does not have bathrooms, gas stations or cell service, so plan accordingly!

Day 6: Portland, Maine (3h From Bar Harbor)

Why Portland Next? Not only is Portland a very cool city with lots of history and an awesome culinary scene, it’s also on the drive back toward Boston. Portland has a great mix of urban vibes and authentic fishing port scenery, so it offers the best of both worlds, too.

Here are some awesome things to do in Portland:

→ See all 3 of Portland’s lighthouses . If you only have time for one, however, make it Portland Head Lighthouse. This is one of the best lighthouses in New England, and definitely worth your time! But keep in mind that the other two lighthouses (Bug Light and Spring Point Ledge Light) are a very short drive away, so it’s easy to see all three in a few hours at most.

→ Take a tour! This culinary walking tour of the city is a great way to enjoy the best food, and this tall ships cruise around the bay is an awesome scenic option to get the most out of your visit.

→ Go beer tasting . Portland is home to some of the best breweries in New England, and the city has tons of them. I have an entire guide on my favorite breweries in Portland, Maine , if you’d like some suggestions 😉

→ Wander through Old Port , the most historic and charming part of the city.

Hotel Suggestions in Portland:

Splurge : The Press Hotel . It’s right on the water and in the center of Old Port, making this an awesome hotel to splurge on for a fancier stay in Portland.

Moderate: Cambria Hotel . Also in the Old Port district, this lovely hotel has modern rooms and a great location.

Budget: Black Elephant Hostel . Portland tends to be a pricey city to visit, and even though this is the only hostel in the city, it’s incredibly well-regarded, and will be significantly less expensive than a hotel.

Pro Tip : If you would rather spend your first day in Portland exploring the city, you can do the lighthouses the next morning on your way back to Boston. The lighthouses are located outside of the city’s downtown in South Portland, which you’ll pass through on your drive to Boston.

Optional stop to make on the drive : There are some wonderful towns to explore on the drive from Bar Harbor to Portland, and I detail my favorites to suggest in my guide on driving from Portland, Maine to Acadia National Park . Many of these stops will add extra time to your drive, but depending on your road trip style, they may be worth it for you!

Day 6: Alternative Option: Stay In A Smaller Coastal Town Instead

If staying in a city isn’t exactly your speed, and your goal is to visit more of the smaller towns along the coastal, well I’ve got you covered. And honestly, that’s usually my preference, too 😉 While I love Portland, and think there’s some very cool things to see there, one of the best parts of New England is the charming smaller towns to explore.

My favorites to suggest for this road trip are: Boothbay Harbor, Kennebunkport, and Ogunquit.

Boothbay Harbor is a wonderful, charming little town on the water, and has a more fishing village vibe to it. Lots of awesome boat tours depart from here, too.

Kennebunkport perfect encapsulated New England coastal beauty with a wonderful town center called Dock Square, and beautiful coastline near the beaches and on Cape Porpoise.

Ogunquit is also very idyllic, and is known for having one of the best beaches in New England. I love the walkable downtown that’s also walkable to the beach. Ogunquit also has one of my favorite things to do in all of New England: the Marginal Way coastal walk.

All of these places will make a great place to spend a night on this road trip if you’d prefer a small coastal town over staying in a city like Portland.

Psst! I have detailed guides that may help you decide, which are the best things to do in Boothbay Harbor , and the best things to do in Ogunquit .

Day 7: Back To Boston With Stops Along The North Shore (2h Without Stops)

Why The North Shore Next? As you make your way back to Boston, you’ll drive down the Massachusetts North Shore, which is packed with gorgeous and charming little coastal New England towns . These towns are all pretty close to another, too, which makes it easy to stop in quite a few during your drive. These towns are actually some of my favorites in all of New England.

Here are some more towns you can choose to stop in on your drive back to Boston:

→ Portsmouth, NH – while not technically part of the North Shore, it’s along the route, and a very beautiful coastal city with awesome shopping and restaurants.

→ Newburyport, MA – Some of the best shopping in New England can be found here in Market Square and Tannery Marketplace. It’s also home to Plum Island.

→ Rockport, MA – One of my all-time favorite coastal towns because it’s so unique and loaded with character. This one is a bit of a detour off the main route, but not by much (and worth it, in my opinion).

→ Salem, MA – Most known for its Halloween celebrations, but is a very beautiful and charming city that’s awesome year-round.

→ Marblehead, MA – An underrated town that’s very beautiful and historic, and loaded with gorgeous coastline.

Where you choose to stop will largely depend on how much time you have, and I honestly think they’re all worth your time! Of them all, I think I prefer Rockport the most, as I think it has the most unique scenery,, but you can’t go wrong with any of the places I mentioned above. I’ve been to them all, and continue to visit them all regularly 😉

Here are some posts that will help you plan your drive down the North Shore:

• Best Things To Do On Cape Anne (part of the North Shore)
• Best Things To Do In Marblehead, MA
• Best Things To Do In Rockport, MA
• Best Stops To Make Driving Boston To Portland, Maine
• Best Things To Do In Newburyport & Plum Island

Alternative option : If you didn’t stop in Ogunquit or Kennebunkport the night before, these two coastal towns are also worthy of your time!

10 Day New England Road Trip Itinerary

With 10 days for your New England road trip, we can pack even more exciting places to visit into your itinerary!

I’ve broken down this 10 Day New England road trip itinerary for you below, and since many of the same stops are included, I’ve done a more abbreviated version. You’ll want to refer to the above 7 Day Itinerary for all the important information. But don’t worry! I’ve included all my pro tips for the new additions to this option, too.

Days 1-2 : Boston , with an optional day trip to Salem, Provincetown or a whale watch tour from Boston’s Harbor. Since you have the extra day, I suggest taking a day trip to one of these 3 destinations, but if you would prefer to relax and explore the city even more, you can do that, too.

Day 3 : Newport, RI .

Why Newport, RI Next? It’s only 1 hour and 30 minutes from Boston, and such a beautiful coastal town to visit in New England. Because of its location, it makes it easy to squeeze into a 10-day New England itinerary, too.

Here are some suggestions of awesome things to do in Newport, RI:

• Explore Cliff Walk.
• Tour the stunning Gilded Age mansions.
• Have lunch at Cliff House.
• Take this awesome morning mimosa boat tour in Newport!
• Explore the city by trolley, which includes The Breakers mansion!

Psst! I have a detailed guide on the a Newport, RI day trip , which is helpful for 1-night stays, too 😉

Newport, RI hotel suggestions:

Splurge: The Cliffside Inn , which is walkable to Castle Hill Lighthouse, pictured above!

Moderate: Mill Street Inn , which is in a historic building that’s walkable to a lot of places downtown, including the waterfront. They also have a great rooftop patio!

Day 4 : Woodstock, VT

Days 5 : White Mountains, New Hampshire

Day 6-7 : Acadia National Park & Bar Harbor

Day 8 : Boothbay Harbor, ME

Why Boothbay Harbor Next? As mentioned, one of my favorite little coastal towns in Maine is Boothbay Harbor because it’s loaded with charm and character, and offers so many incredible opportunities to get out onto the water with boat tours. Of all the places you can stop at on your way from Acadia to Portland, this is one of my favorites.

Here are some wonderful things to do in Boothbay Harbor:

• Take this awesome boat cruise to see seals, lighthouses and a lobster haul tour!
• Stroll through the adorable downtown area.
• Take in the views from the footbridge.
• Have a delicious lobster roll at Shannon’s Unshelled.

Hotel Suggestion in Boothbay Harbor:

The Harborage Inn on the Oceanfront is my favorite place to stay in Boothbay Harbor. The location is perfect and walkable to town, but set back enough so that it’s very peaceful. If you can, splurge on Room 8 for panorama views of the water (it seriously feels like you’re floating on water).

Day 9 : Portland, ME

Day 10 : Back to Boston, making stops along the North Shore on the way.

A lternative suggestion : If you wanted to skip Woodstock, VT for this option, you could add an extra day in the White Mountains. You could also skip Woodstock and add a night in the North Shore on your drive back to Boston. For this option, I would suggest Newburyport.

Do I still think Woodstock, VT is worth the excursion? Yes! But an extra day in the White Mountains or a night in the North Shore may appeal more to some of you, too. Do what fits your preferences the most 😊

I love Newburyport because it’s a wonderful balance between charming coastal town and historic shopping village. It pretty has much something for everyone, including a beautiful waterfront park, the nearby Plum Island for beaches and nature trails, and some of the best shopping in New England. For this particular itinerary, I think it’s a great option because it’s also the furthest north, and will break up your trip nicely.

Here are some fun things to do in Newburyport:

• Induldge in some retail therapy in Market Square and Tannery Marketplace.
• Walk the path in the Waterfront Park.
• Explore Maudslay State Park .
• Drive to Plum Island to see the beaches and the nature trails at Parker River National Wildlife Refuge.

Newburyport hotel suggestion:

Compass Rose Inn is the best place to stay in Newburyport and feels like a big, warm hug when you arrive. In a beautiful and historic home, and each room is a suite with a fireplace. It’s also walkable to town, and a complimentary breakfast is included.

5 Day New England Road Trip Itinerary

Don’t have 7 or 10 days for a New England road trip? No problem! Having put a lot of thought into the best 5 Day New England itinerary, you can easily make this a jam-packed road trip style trip, or a more relaxing getaway that allows you additional time at each destination, but doesn’t get to as many places. Not sure which is right for you? I’ve outlined both to help you decide.

As before, refer to the first 7 Day New England road trip itinerary option for more detailed information on each destination.

5 Day Road Trip Itinerary From Boston

Day 1 : Boston

Day 2 : The White Mountains, New Hampshire

Day 3-4 : Acadia National Par k

Day 5 : Drive back to Boston , stopping at the Portland Lighthouses, and 1-2 towns along the North Shore region on your way.

5 Day Relaxed Itinerary From Boston

Days 1-2 : Boston. Two days will allow you to settle in and enjoy a more relaxed pace.

Pro Tip : If you’re not flying into Boston (ie, you’re driving in), you don’t have to stay right in Boston. You can definitely stay in a cute nearby town like Salem or Gloucester, and then take a day trip to Boston for a more relaxing getaway.

Days 3-4 : Newport, RI & Mystic, CT. From Newport, Mystic, CT is only about a 1-hour drive, which makes this an easy and relaxing afternoon excursion that’s stress-free.

Psst! I have a detailed guide on the best things to do in Mystic, CT , if you need more ideas 😉

Day 5 : Back to Boston, with stops in either Plymouth and Scituate on the way back (or both!). These two towns are south of Boston, and more convenient to visit when driving from Newport. I love them both, and they offer lots of charm, shopping, dining and beautiful sites to see. Of the two, Scituate is smaller with fewer things to do, but very beautiful.

Alternative suggestion 1 : Stay right in Boston for all 5 days, and take day trips! Since Boston is in such a great area, it’s very easy to get around. And as mentioned before, you can take a ferry to Provincetown on Cape Cod, or over to Salem, and you won’t need a car for either of these two excursions.

Alternative suggestion 2 : Stay in Boston for 2-3 nights, and spend 2-3 nights on Cape Cod with a day trip to one of the islands (Nantucket or Martha’s Vineyard). This option will be very coastal, and provides you with some of the best beaches and coastal towns in Massachusetts.

Here are some posts that may help you if you like this option:

• Best Towns To Stay In On Cape Cod
• Best Things To Do In Provincetown, MA
• Cape Cod Day Trip Guide
• Martha’s Vineyard Day Trip Guide
• Nantucket Day Trip Guide
• Is Nantucket Or Martha’s Vineyard Better For A Day Trip?
• How To See Martha’s Vineyard Without A Car

Alternative suggestion 3 : Stay in Boston for 2 nights, and then drive to the North Shore for 2 nights, and then maybe Portland for 1 night. Just north of Boston, the North Shore region includes Salem, Marblehead, Manchester-By-The-Sea, Gloucester, Rockport, Essex and Newburyport. All of these towns are pretty close to another another, and it would be easy to pick one to stay in, and take afternoon trips to the others.

Portland is also within 1 hour and 30 minute at the most from these towns, making it easy to pop over for the day, or a night.

Best Way To Get Around New England

The best way to see New England is definitely by car. If you fly in, I suggest renting a car from the airport to begin your road trip. If you plan to spend a day or two in Boston before beginning the road trip, I would say to hold off on renting your car until you’re ready to leave Boston.

Boston has an awesome public transit system, and Uber and Lyft are readily available, so a car will be more of a hassle to park in the city.

What To Pack For A New England Road Trip

This will, of course, depend on entirely on the time of year you visit, as New England is a four-season climate. I always suggest checking the weather reports a few days before leaving to get a more accurate idea of what the weather and temperatures will be like.

I love to remind people that New England can be moody and weather can change frequently. Even in the summer, you could have chilly days, and in the winter, you might experience a warm day. Although, generally speaking, you’ll find it’s pretty much what you would expect of a four-season climate: A wet and rainy spring, a warm or hot summer, a chilly fall, and cold and snowy winter.

Here are a few suggestions and tips on packing for a New England road trip that you not have thought of:

→ A reusable water bottle to reduce single-use plastic.

→ Dramamine if you plan to do any boat tours, and you’re prone to seasickness.

→ Day pack for essentials like your water bottle, camera, sunscreen, etc.

→ Comfortable shoes for exploring towns. Keep in mind that places like Boston, Nantucket, and historic small towns often have uneven cobblestone or brick streets.

→ Hiking boots if you plan on doing any hikes.

→ In general, plan to keep your clothes fairly casual. New England can be fancy if you plan a special dinner out, but is overall pretty casual. Take a look at your specific plans and eliminate any extra fancy outfits that you likely won’t need. You probably won’t need any if you don’t plan to dine out anywhere upscale.

→ Light jackets or sweaters for mornings and evenings (even in the summer!).

→ Waterproof jacket and boots if you plan to visit in the spring or fall.

→ Don’t forget your camera! You may also want to consider an iPhone tripod with a remote shutter to elevate your travel photos from selfies to wall-worthy shots. This one on Amazon is inexpensive and perfect for the average traveler!

New England Road Trip FAQ

Is new england easy to drive around.

Very! Of course, you’ll experience traffic when you’re close to, or in, a city like Boston or Portland. In that case, it’s just like driving in any other city. But overall, New England is very easy to drive around.

One thing I like to remind people is that in the more rural places, you will likely drive on a lot of dirt roads, so just be careful of any pot holes and go slowly, especially in Vermont and New Hampshire.

Is It Safe To Take A Winter New England Road Trip?

Yes! As long as you’re comfortable driving in the snow, you’ll be totally fine. Chances are, if you’re visiting in the winter, you’re excited to check out places like New Hampshire or Vermont, and those two states are among the top 3 snowiest in the whole country. So, just know that you will experience snow, and you’ll definitely be driving in it.

But generally speaking, most places are great at plowing roads, so unless you happen to visit during one of our big nor’easter storms, driving is easy. Just practice normal precautions, and don’t drive if the snow is coming down really hard.

I have an entire guide on all my favorite New England winter getaways , if you’re looking for the best winter destinations in this region.

Is Cell Service Reliable All Over New England?

Yes and no, and it depends on where you’re going. For the most part, cell service is completely reliable, and Google Maps will be able to take you everywhere.

However, in more remote places, again like in Vermont or New Hampshire, or even along the coast at some lighthouses or in Acadia, you will lose cell service more than you think! I highly recommend offlining maps for your entire route just to be safe . I can’t tell you how many times I’ve lost service while driving in VT and NH and didn’t offline maps, only to very much regret it in the moment!

Why Is Connecticut Not Part Of Your Itineraries?

I love Connecticut! But the hard thing about it is its location. It’s so far southwest, in the exact opposite direction of Acadia National Park, and most of the other top destinations to visit. And since Acadia is one of the most amazing New England locations that everyone should see when they visit, I had to exclude Connecticut from the itinerary options only for the sake of time. I personally think Acadia, and the other places I’ve mentioned, offer much higher payoff for your driving time than destinations around Connecticut.

That’s why I was only able to squeeze in a quick afternoon trip to Mystic, CT in the 5-day option.

What About A Fall Foliage Road Trip?

I’ve got you covered! I have an entire post on the perfect New England fall road trip , which is one I’ve perfected over many years of exploring this region in the fall season. This road trip makes stops in similar places, but has more of a focus on the best places for foliage.

You May Also Enjoy Reading:

• Best Things To Do In New England
• Best Time To Visit New England
• Incredible New England Resorts & Spas
• Best Boston Hotels Near The Aquarium
• Awesome New England Gifts & Things To Buy During Your Visit
• Best Christmas Towns in New England
• Best New England Day Trips
• Summer In New England: Best Places To Go & Things To Do!
• Best Beach Towns In New England
• Things To Do In Boston In The Fall
• Gorgeous New England Islands Worth Visiting
• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary

That’s A Wrap On The Best 7 Day New England Road Trip Itinerary

Hopefully you’re now feeling ready to tackle planning your own adventure with this 7 Day New England Road Trip Itinerary! Even with 7 days, you can see so much of this gorgeous region and really cover a lot of ground. And, of course, if you have time to follow along on my 10 Day New England Road Trip Itinerary, that’s even better. But regardless of what you have time for, New England is always a good idea, and is always worth making time for. Happy planning!

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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Save this Northeast Road Trip Itinerary for later! 

• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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The Ultimate New England Road Trip Itinerary

New England has some of the most beautiful scenery in the United States. However, if you are planning on taking a New England road trip, you need to plan ahead. There is so much to see and do that it can be easy to burn through a 5-day New England road trip without having seen nearly all that you want to see.

Part of it is proper time management. You definitely cannot wing it when checking out New England vacation spots. There is so much to do on the New England coast alone that you will need to take more than a few trips to see it all.

A map of New England is just the starting point. Plan your New England coast road trip with a 7-day New England road trip itinerary. There are key points to hit the first time to see the essential things the first time around.

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How to Prepare for a New England Road Trip

It helps to have an RV Generator when planning a New England road trip itinerary, especially taking a recreational vehicle. This way, you have fuel to cook with, and you can run minor electronics off of it for a little while at a time. It makes the road trip a little more like home while on the road.

You also have two options. You can get a New England map and do it like the old days. Or you can find a digital map of New England states online anywhere. Just make sure you scout ahead because New England weather can be finicky, and you can be taken by surprise by the conditions.

Make sure that you have an idea of New England tours available when you go, too. Tons of great tours show all the historical sites in the area, allowing you to get the most of the vast history that the area has to offer.

Finally, make sure you are familiar with New England law. Some things might take you by surprise if you are not adequately prepared. Even just a quick overview is enough to give you an idea about what to expect.

There are plenty of excellent road trip options, especially for those looking for ways to spend time with their families . Here are the best options when planning your itinerary.

5 New England Road Trip Itineraries

Are you looking for a good New England road trip itinerary? Everyone who has been to the area will no doubt have their suggestions. The key is to make sure that time is managed efficiently to be seen during the trip.

There are plenty of essentials to see, but which places do you have to go to in a shorter period? Here is the itinerary that will leave you feeling great about your trip and make you want to come back a few more times to see everything else.

1. Downtown Boston

If you are planning a Boston vacation of any kind, you know that you could easily spend the entire trip in Boston. It is one of the most historical and famous cities in the United States, and there is more to do than you could imagine.

Where is Boston, you may be asking? It is the heart of New England, one of the biggest cities on the east coast, located in Massachusetts. It is a destination for millions every year and one of the most popular cities there is.

You can start around the greater Boston area, hitting up some of the most famous things like the old Boston Garden. Catching a game at Fenway Park is another must as the Red Sox are a staple of Boston and America. Or you can just tour Fenway Park.

It is also one of the most historical places in the United States, dating back to the colonial period when America was just a collection of colonies owned by Britain. It is a great place to learn much about the beginnings of the United States.

Don’t Miss These In Boston

• Boston Ghosts & Gravestones Night-Time Trolley Tour
• Boston’s North End Secret Food Walking Tour w/ Private Tour Option
• Martha’s Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

2. Maine National Parks

You have no doubt heard about Bar Harbor, Maine. But what is it? What to do in Bar Harbor, Maine, that makes it worth the visit? If you are looking for things to do in Bar Harbor, Maine, look no further than the largest national park in the country.

The national parks in Maine are worth the trip alone. It is the largest national park in the US, and the park loop road will keep you busy for far longer than you could have ever hoped. Whether you are someone who enjoys the outdoors or not, you will love these national parks. Wolfe’s Neck Woods State Park, in particular, is a favorite among locals and tourists alike.

Don’t Miss These In Maine

• 2-Hour Tall Ship Cruise from Bar Harbor
• Narrated Bus Tour of Bar Harbor and Acadia National Park

Whereas Boston is a great place to see historical sites, Maine is the place to go for those who love the outdoors. The beautiful national parks will keep you occupied for days and definitely will be something you want to see again.

3. Vermont Cities

Vermont tends to get lost in the shuffle when thinking about the destinations in New England. But cities in Vermont, particularly the small towns in Vermont, can wind up becoming significant destinations. The biggest cities in Vermont have that quaint feeling, though, which makes it feel like small-town life no matter where you are.

You can also partake in many outdoor activities. Ski-in ski-out Vermont, check out Crystal Lake Vermont for some stunning outdoor scenery, and Rocky Neck State Park is camping for a unique outdoor experience like no other.

Don’t Miss These In Don’t Miss These In Vermont

• Day Tour through Stowe,
• Vermont Snowmobile Tour ~ St Johnsbury Vermont’s

New Haven city hall is a historical destination as Vermont is also from the colonial era though it doesn’t get nearly as much love as Massachusetts. There is much and more to do in Vermont, even if they may not jump out immediately.

4. Cities in Connecticut

Like Vermont, Connecticut towns don’t get the love that they should. Connecticut National, Connecticut River Valley, and Connecticut beaches are beautiful and one of the hidden gems of the entire New England region.

The best beaches in Connecticut rival some of the best beaches in the country. Even better, they are not relatively as crowded as some of the popular ones in, say, Florida or California. That means being able to spend time quietly on the beach, enjoying the sun and the sand.

Much like Boston and Vermont, there are plenty of historical sites to see as well. There are more than a few trips worth of historical sites worth visiting in New England for those who consider themselves to be history buffs. Even if history isn’t your thing, there are more than a few sites that can get even the furthest thing from a history buff interested in the beginnings of the United States.

5. Cape Cod Town

Cape Cod weather is an attractive aspect in itself. The Cape Cod Canal is a destination for those in New England looking to take a trip but stay within the region. The National Seashore in Cape Cod is one of the most beautiful areas in the region and a must-see for locals and visitors alike.

Race Point offers some of the most beautiful, sandy beaches that you could hope to see as well. And because it is in New England, you can also get a little bit of a historical touch with the Race Point lighthouse. It is the perfect combination.

Cape Cod Town is home to some of the most beautiful natural scenery in New England. There is so much more than meets the eye, from the trails to the beach, the heritage museum, to the Pilgrim monument. It is an eye into the area’s history without being a little too “boring” like some historic areas.

Don’t Miss These In Cape Cod

• Cape Cod Sunset Private Charter
• Open-Air Pedicab Tour in Provincetown
• Whitney Plantation Audio Tour

There are plenty of things to do in Provincetown, too, from a great food scene and even the excellent Provincetown beaches. You can get the best of both worlds depending on where you go, with warm days to spend at the beach and crisp evenings to get the entire New England atmosphere.

Closing Thoughts

There is so much to see and do in New England that you can’t possibly hope to see it all in one trip. Still, with the proper itinerary, you can make the most of your 5- or 7-day New England road trip and get a ton fit into one trip.

When you have the proper itinerary, not only can you hit the essentials, but you can get an idea of what you may have missed. Besides, you will want to come back for more than a few trips to see all that New England has to offer.

Not only that, but you can also get a better idea of what weather may be like during that time of year, what to expect from road conditions, what you might spend on things like food, and more. You will become an expert on New England road trips in no time and better prepared when you inevitably go back in the future.

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Nikki Webster is a travel writer who covers how to travel while grinding a day job without breaking the bank. Nikki is always in search of off-the-beaten-track experiences and unique stays. She is particularly fond of Florida and writes extensively about the state. She flies around 60,000 miles annually and has visited 74 countries, 50 states, and six continents. You can read all about her travels at www.britonthemove.com or follow along on Facebook, Pinterest, and Instagram.

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10 Absolutely Beautiful Spots For A Coastal Road Trip In New England

S aying there's a lot of lands to go through New England would be an understatement. Covering a total of 6 states across almost 72,000 square miles in the northwestern region of the US, and being home to some of the country's most scenic drives available, make it a dream destination for nature travelers. All while still having Boston add some welcome city charm .

However, most people get drawn only by the parks and peaks without realizing the greatness of New England's coast. And, with hundreds of roads at their disposal, visitors are bound to come across many of the wonderful sceneries that litter the region. There are some spots that stand out, though, and that are a must for anyone taking a coastal road trip in New England.

Related: Road Trip New England: See Six States In Two Weeks

Essex River Valley

Being called "New England", there are bound to be places named after Old England cities. Unlike its European namesake, Connecticut's Essex is a nature-filled haven where trees adorn the land in outstanding colors, especially during spring and fall. And it just so happens that it's where the longest river in New England discharges into the Atlantic Ocean.

The River Valley section of Essex is filled with both beauty and history, as one of the main attractions to be found are two totally functional relics of 19th century America: a Steam Train and a Riverboat that take passengers along the same route they had over a hundred years ago.

Rangeley Lakes

One thing that makes Maine great is the number of seafood dishes that can leave anyone's mouth-watering , and, besides being plentiful in lobster, Maine's waters give the state a unique feeling of amplitude and peace.

Once arriving at Maine's coastal area, the first thing that will take any driver's breath away is the 6 beautiful lakes that make up the Rangeley Lakes range . Each lake is surrounded by plentiful forests that offer a changing scenery as seasons change and a huge variety of wildflowers to make each patch of land different from the other.

Mount Desert Island

Also in Maine, breaking off from Trenton's main road, Mount Desert Island is a place surrounded by water and mountains that mix inland and coastal settings in parks, gardens, and harbors that make the most out of the island's natural richness. It's the largest island in all of Maine , and it got its name after explorers marveled at the sight of mountains without a single tree on them, as if they were deserted, even though the area was covered in forests throughout the land.

Related: This Mount Washington Hotel Is New England's Most Haunted (Here's Why)

Acadia National Park

Speaking of the parks inside Mount Desert Island, one of the United States' most astounding national parks is placed mostly within the island's region. The Acadia National Park is a destination that has to be on every hiker's bucket list . Covering over 48,000 acres across several islands of Maine's southeastern coast, with the tallest mountains on the eastern seaboard and great subalpine rocky summits.

The area's lush land and diverse ecosystem make it a must to pass by when exploring the East Coast on a coastal road trip in New England, and although some parts are not entirely accessible by car, there are still great short trails that manage to encapsulate the park's marvelous scenery.

Green Mountains

Although it's the only state within New England that's not in direct contact with the coastline, Vermont holds many picturesque landscapes that make it well worth it to take a small detour from the beaches to gaze upon the state's mountainous landscape.

One of the most prominent mountain ranges, which has given Vermont the nickname of the Green Mountain State, is, obviously, the Green Mountains .

Extending over 250 miles through Vermont, in an array of peaks, lakes, and forests that make for outstanding drives and breathtaking hiking trails.

Mount Mansfield

Also within the Green Mountains range, standing at just over 4,300 feet above sea level, Mount Mansfield is the tallest peak in all of Vermont . The trails that track up to the peak of the mountain might look peaceful thanks to the grass and flowers that cover the hills, but it's actually considered an extremely difficult way up due to rock scrambles and ledges along the way. Luckily, it's enough to just be able to watch it from a distance while it towers above Vermont's landscape.

Shore Of Dreams

Thanks to the number of charming small towns on the island and the calm views available along the way, Rhode Island's most famous scenic drive has been aptly named the Shore of Dreams . Following 43 miles along Narragansett and Ocean Road through beaches, cottages, and historical landmarks from over 140 years ago. And, after spending a couple of hours driving, there's always the option of sampling Rhode Island's signature dishes right next to the shore .

Related: These Lovely Towns On The Cape Cod Coast Are All New England Charm

The Berkshires

Proving that the highland can bring as much charm and attitude as the coastline, The Berkshires is a historical and cultural piece of North America's past . Receiving its name from Berkshire County in England, the region consists of all the highlands in western Massachusetts, west of the Connecticut River. The roads journey through the land's many rivers and perfectly-preserved 18th-century architecture that make a great break between the arboreal scenery.

White Mountains

Similar to the Green Mountains in Vermont, the White Mountains are New Hampshire's crowning glory. Making part of the Appalachian system of mountains and standing at an astounding 6,300 feet above sea level, the mountains' peaks beautifully cover themselves with snow during winter, which is what gave them the name and color themselves in shades of green, red, and yellow for every other season.

Mystic Village

A small coastal village filled with 17th-century buildings and a fully functional cider mill? Yes, please. The village of Mystic might not beat Bridgeport in size or population, but it sure has more history with an intact New England charm still attached to it . Founded around 1654, Mystic is one of Connecticut's oldest standing settlements, and it has been able to maintain most of its older buildings in service, while repurposing some as the village's attraction points. If that's not enough, the Olde Misticke takes a step further and shows tourists how things were in the old days, from look to even food.

14-Day New England Road Trip Itinerary

United States

• New England

My favorite way to discover a new destination is by going on a road trip, and I had my sights set on New England. This historic region has its roots in America’s foundation and has many of its first resort towns. With its sandy beaches, colourful foliage, crystal-clear lakes, and craggy peaks, New England has immense natural beauty.

Thanks to its relatively small size, New England is one of my top picks for road trips in America. You can drive through some states in a single day, and there’s almost always a convenient place to stop. From the sea to the mountains, the scenery changes before your eyes to create an unforgettable vacation.

To get the most of your New England road trip, I devised a 14-day itinerary that takes you through seven beautiful states. Our road trip route takes us through all six of the traditional New England states, and I also added a couple of days in New York State. Between the beaches, mountains, and enchanting towns, I think this itinerary hits a little of everything.

Fill up the car, buckle up, and get ready for the ultimate New England adventure!

Starting Destination: Boston | Day 1 – Boston (MA) to Cape Cod (MA) | Day 2 – Cape Cod (MA) | Day 3 – Cape Cod (MA) to Newport (RI) | Day 4 – Newport (RI) to Litchfield (CT) | Day 5 – Litchfield (CT) to Adirondacks (NY) | Day 6 – Adirondacks (NY) | Day 7 – Adirondacks (NY) to Green Mountains (VT) | Day 8 – Green Mountains (VT) | Day 9 – Green Mountains (VT) to White Mountains (NH) | Day 10 – White Mountains (NH) | Day 11 – White Mountains (NH) | Day 12 – White Mountains (NH) to Acadia National Park (ME) | Day 13 – Acadia National Park (ME) | Day 14 – Acadia National Park (ME) to Boston (MA) | Depart Logan International Airport

Starting Destination: Boston

One of America’s most historic cities, I thought Boston was a great destination to begin my New England road trip. As the region’s biggest city, Boston beams with culture, world-renowned universities, and American Revolution monuments. In particular, the Freedom Trail stood out as a fascinating attraction to visit museums and historic sites. Boston also has fantastic eateries, great craft breweries , shopping galleries, pulsating nightclubs, performing arts theatres, and harbour cruises. It’s a bustling metropolis, and I think it’s worth spending a few days here before hitting the road.

If you’re flying into Boston, then Logan International Airport is where you’ll arrive in the city. The airport is less than five miles from downtown Boston, and there are plenty of car rental agencies to find a vehicle. Rentals from the downtown Boston area are typically more affordable than those from Logan International Airport. The fastest way from Logan to downtown Boston is through Charlestown, North End, or South Boston Waterfront via water taxi. Boston also has a subway system, and taxis are available from the airport.

I would advise you not to pick up a car rental in Boston until you’re ready to depart for your New England road trip. Driving around Boston is extremely challenging due to winding roads, unexpected one-way streets, and GPS inaccuracy. Plus, parking fees across Boston are outrageously high and not worth just a few days in the city. If you’re on a budget, then this will quickly eat into your funds for the rest of your vacation.

Trust me; that wouldn’t be any fun. However long you wish to explore Boston , don’t pick up the car until the day you leave this amazing New England metropolis.

Day 1 – Boston (MA) to Cape Cod (MA)

To kick off my 14-day adventure, I decided to drive south of Boston to the sandy shores of Cape Cod . This popular summer retreat is about 1-2 hours from Boston, depending on your exact destination on the Cape. It was tough pickings where to stay in Cape Cod due to all the charming seaside towns on the peninsula. Sandwich, Chatham, Dennis, Eastham, and Provincetown are just a handful of my top recommendations. U.S. Route 6 is the primary thoroughfare through Cape Cod and provides a scenic drive across the peninsula.

Ultimately, I decided to drive the entire peninsula through Cape Cod National Seashore and stayed at vibrant Provincetown. Regarded as an artist haven, Provincetown enchants you with its pilgrim monuments, historic homes, art galleries, lighthouses, and pristine beaches. Commercial Street is where you’ll find fabulous seafood restaurants, and sunsets on Race Point Beach offer stunning portraits. After driving nearly 120 miles from Boston, it was the perfect spot to stretch my legs and hear the ocean waves.

Just south of Provincetown, the Atlantic side of the Cape from Truro to Chatham beckons surfers. With about 1,500 miles of coastline, Massachusetts has dozens of beaches to take your surfboard and Cape Cod features much of the best surf in Massachusetts .

Day 2 – Cape Cod (MA)

Before I left Massachusetts, there was one summer activity I had to do while staying at Cape Cod. From Provincetown, I embarked on a whale watching tour to watch these majestic animals in their natural environment. There are several whale watching tour companies based around Provincetown Harbor to host your voyage. Although whale watching season is from April-October, June-September is the best time to spot marine creatures.

On your cruise, you could see Humpbacks, Finbacks, Minkes, and dolphins. From the vessel, you’ll also have the chance to take incredible photos of the beaches and lighthouses of Cape Cod National Seashore. This 3-4 hour trip topped my highlights on the New England coast.

Although I wanted to explore the sea, the area has tons of outdoor activities on land as well.   Your options include bike trails, sand dune hiking paths, and woodland nature preserves. Before packing the car, dine on more succulent seafood and famous Cape Cod ice cream. There are a lot of fun things to do in Provincetown so even if outdoor activities is not your thing you wont get bored.

A tasty way to end a delightful day in Cape Cod!

Day 3 – Cape Cod (MA) to Newport (RI)

The next place on my road trip itinerary was the smallest state in America, Rhode Island. Despite its meagre size of 1,212 sq miles, Rhode Island packs many New England gems inside its borders. I could’ve spent more time exploring Rhode Island’s colonial towns, white-sand beaches, and beautiful architecture, but other states were higher on my list.

Around 2.5 hours from Provincetown, Newport was one Rhode Island destination I wanted to check out. This elegant resort town for the rich and famous dazzles visitors with its Gilded Age mansions and a yacht-filled harbour. The 10-mile Ocean Drive showed off spectacular seaside views and lavish homes dotting the Atlantic Coast. If you’d rather spend the day lounging on the beach, check out Easton’s Beach or Third Beach. Other attractions in Newport include The Breakers, Fort Adams State Park, and the Cliff Walk.

Providence, the Rhode Island capital, lies about 45 mins north of Newport. However, I bypassed the city life and stuck with the surreal coastal views before I ventured inland.

Day 4 – Newport (RI) to Litchfield (CT)

Instead of driving north back towards Massachusetts, I decided to head westward into Connecticut. Upon leaving Newport, I made a pit stop in the charming seaside town of Narragansett to admire those Rhode Island surf beaches one last time. My advice is for Rhode Island is to run straight to the sea; it’s such a relaxing place to be and one of the perfect romantic getaways in Rhode Island as well.

Once I entered Connecticut, it was time to start making my way towards the mountains and maybe stop at one of Connecticuts wineries on the wat. If you can’t get enough coastal charm, one Connecticut destination to stop is the seaport town of Mystic. Just a 45-50 minute drive down U.S. Route 1 South from Narragansett, Mystic is a delightful spot for lunch and shopping. Dine on seafood, stop by the famous Mystic Pizza, or have ice cream beside the drawbridge.

As I continued my drive through the Connecticut countryside, I came across an underrated New England gem. Tucked away in the northwest corner of Connecticut, the Litchfield Hills prepped me for future mountain views. The area beams with rustic towns, adorable farms, and trickling waterfalls. If you drove through this area in fall, the colourful foliage would take your breath away. This quaint section of Connecticut is made for nature lovers and offered way more than I expected. And given Connecticut’s small size, I made it here from seaside Mystic in under two hours.

Day 5 – Litchfield (CT) to Adirondacks (NY)

New York isn’t one of the traditional New England states, but it has some of the best mountain views in this region of America. The Adirondacks were towards the top of my list, and I had a long drive from Connecticut. Roughly 2.5 hours from Litchfield, my final destination for the evening was Lake George.

Situated on a deep-blue lake of the same name, Lake George is a year-round Adirondack getaway. The scenic drive towards northern New York offered beautiful views of the Catskill Mountains near the Hudson River and capital Albany. Once you pass the capital, it’s a straight-forward drive on I-87 North to Lake George.

Those Adirondack views shine overlooking the lake, and it’s a delightful place to relax for the evening. Whether you decide to book a Lake George cruise or lounge on Million Dollar Beach, you can’t go wrong at this lovely resort town. Just make sure to drive Prospect Mountain Highway before it gets dark for an unbelievable Lake George vista.

Day 6 – Adirondacks (NY)

Using Lake George as my base, I decided to spend another day in northern New York and the Adirondacks. With over 6 million acres of pristine wilderness, Adirondack Park is a nature lover’s paradise. Dozens of peaks soar over 4,000 feet, thousands of lakes create aquatic adventures, and more than 100 charming towns call this beautiful region home. You could spend a lifetime in the Adirondacks and hiking in New York, and you still won’t discover every inch of its natural beauty.

For my full day here, I ventured to several of the famous lakes sparkling beneath the massif. After checking off Lake George the previous day, it was off to more Adirondack wonders. My first stop was Lake Placid to explore the village that hosted the Winter Olympics twice. Mount Van Hoevenberg hosted many of the events, and snow-topped Whiteface Mountain sits high above the lake.

Just 10 miles from Lake Placid, Saranac Lake is another beauty where the foliage glistens on the water. My final stop was the freshwater Lake Champlain that sits on the New York-Vermont border. As one of America’s largest lakes, it’s a boating and kayaking paradise. There are several gorgeous state parks here, such as Cumberland Bay State Park and Niquette Bay State Park on the Vermont side.

Day 7 – Adirondacks (NY) to Green Mountains (VT)

Since Lake Champlain straddled Vermont, it made the perfect place to spend the night and start the following day. From its dazzling shores, I began my journey to the Green Mountains of Vermont. The mountain range runs north-south across the entire state, but I stuck to the northern side for my travels. Ultimately, the mountain resort town of Stowe was where I set my GPS.

Stowe is about 2-2.5 hours from Lake Champlain, and the route requires a ferry ride. The ferry offers stunning views of the lake and adjacent mountains for a magical crossing beside your car. At just over one hour long, the ferry was the perfect time to relax for a while. Vermont’s foliage is possibly New England’s best, and fall brings leaf peepers from across the globe. Its greenery shines during spring and summer, while the winter months host a snowy wonderland.

From this adorable town, there all tons of activities to have an exciting day. The nearby mountains entice hikers who love chasing waterfalls, and the area has many fantastic eateries. Just make sure you have plenty of energy if attempting to summit Mount Mansfield, Vermont’s tallest peak.

Day 8 – Green Mountains (VT)

Vermont’s scenery was indescribable, and I had to add another day here on my New England itinerary. One of my activities for the day was making the drive down the Green Mountain Byway. Between Stowe and Waterbury, this short journey packed tons of beautiful sights. You’ll pass pristine forests, farmlands, and quaint villages as you travel along the spine of the Green Mountains. With the mountains at your fingertips, the byway is a goldmine for outdoor recreation.

For nature lovers, pit stops at Smugglers’ Notch State Park, Moss Glenn Falls, or Little River State Park are my recommendations. Once you arrive in Waterbury, spend a couple of hours walking around the historic district. I’d also advise stopping by a farmers market to pack your bag for a relaxing picnic. Vermont’s nature is sublime and makes you never want to return to big city life.

Day 9 – Green Mountains (VT) to White Mountains (NH)

After peaceful days in Vermont’s Green Mountains, it was time to drive into New Hampshire to explore the White Mountains. I did much research on this fabled mountain range and its intense hiking trails. Fortunately, it’s a short 90-mile drive from Stowe to reach my White Mountain base. The scenic route crosses through small Vermont towns before entering New Hampshire. Turn onto Vermont Route 15 East and connect to U.S. Route 2 before heading down I-93 South to the White Mountains.

When the granite cliffs came into full view, I couldn’t contain my excitement to continue my adventures. As New England’s most rugged peaks, the White Mountains attract the hardiest hikers in the region. For any readers who love hiking, make sure to place an asterisk beside this spot on your New England itinerary. My final destination for the evening was Lincoln, and I made sure to rest up for some tiring days ahead.

Day 10 – White Mountains (NH)

Prepare to lace up your hiking boots in White Mountain National Forest . Many of New England’s tallest peaks and most challenging treks are in this scenic area of New Hampshire. The Appalachian Trail cuts through the White Mountains and gives AT thru-hikers some of their most intense days. There are so many incredible trails here beyond the Appalachian trail and you can easily find the best hikes in New Hampshire here. For your base location, I think Lincoln is your best bet when exploring the White Mountains. The picturesque town of Jackson is a worthy alternative to base yourself.

For thrill-seekers, summiting a New Hampshire peak should be towards the top of your New England bucket list. At the top of the list is Mount Washington, the tallest mountain in New England. Its summit stands at 6,288 feet, and the climb is among the most dangerous in America. If you’re brave enough to attempt this feat, make all the necessary preparations. Several people have tragically died trying to climb Mount Washington due to falls or severe weather.

While Mount Washington is the life-changing experience I recommend, there are many other awesome day hikes in New Hampshire. Another scenic area of New Hampshire is Franconia Notch State Park, and it has jaw-dropping mountain vistas.

Day 11 – White Mountains (NH)

New Hampshire was my favourite New England state for hiking, and I had to stay one more day. The rugged peaks of the White Mountains offer sweeping vistas, and I wanted to see more. Honestly, I could’ve spent weeks hiking the White Mountains, but two days was okay for my road trip.

My top-rated New Hampshire hike was the Mount Lafayette and Franconia Ridge Trail Loop. The 8.6-mile loop is one of the most challenging New England treks, and it’s only for veteran hikers. You’ll climb three rugged mountain peaks and eclipse 4,000 feet of elevation gain. But the rewarding view from the Mount Lafayette summit makes up for the brutal climb.

Mount Lafayette is the Franconia Ridge’s tallest peak, but it’s my favourite view anywhere in New Hampshire. If you’re eager to add the trek to your itinerary, you may want to camp near Mount Lafayette. Luckily, Lincoln is only 11 miles south and a quick drive from the base down I-93.

Day 12 – White Mountains (NH) to Acadia National Park (ME)

After pushing myself on a couple of daring New Hampshire hikes, it was time to venture to Maine. Situated on Mount Desert Island, Acadia National Park was my destination for this final stage of my adventure. One of America’s most visited national parks, Acadia has over three million visitors per year. With its untouched coastline, pristine beaches, and sparkling lakes, Maine rewards you with nonstop beauty.

Before reaching the Maine coast, I had to drive through the state’s rugged, mountainous interior. The best route from the White Mountains to the Atlantic coast is the 34.5-mile Kancamagus Highway. Otherwise known as New Hampshire Route 112, “The Kanc” is one of my favourite scenic New England drives. From my Lincoln base, I drove the route to the town of Conway. And I was speechless every second of the journey.

The Kanc offers sensational White Mountain views, cuts through enchanting forests, and passes cascading waterfalls. If you can’t get enough of New Hampshire’s incredible hikes, there are many trails and campgrounds here. Some sites I highly advise stopping at include Sabbaday Falls, Lower Falls, the Albany Covered Bridge, and the Rocky Gorge Scenic Area. Leaf peepers will adore this American Scenic Byway for its breathtaking fall foliage.

From Conway, the remainder of the drive to Mount Desert Island takes nearly four hours with no stops. After stopping at numerous scenic viewpoints on The Kanc, I wanted to reach Acadia National Park by nightfall. Bar Harbor was my resting spot for the evening as I rested up for an adventurous day exploring Acadia National Park.

Day 13 – Acadia National Park (ME)

When I organized my New England road trip itinerary, Acadia National Park topped my list of places to see. Its rugged coastline, sandy beaches, and epic hiking trails tapped into my adventurous spirit. Honestly, a road trip through Acadia National Park isn’t enough, and I could spend weeks exploring its awe-inspiring landscapes.

For the sake of this road trip, Park Loop Road is a must-do since it takes you to many of the park’s top natural wonders. After watching the sunrise at Cadillac Mountain, drive the 27-mile route to beloved sights such as Sand Beach or Thunder Hole. For daredevils reading this, the Precipice Trail is an adventure that’ll provide an adrenaline rush. To refuel for lunch, stop by the Jordan Pond Restaurant or have a picnic at Echo Lake.

After a packed day of thrills, my favourite spot to watch the sunset is at Bass Harbor Head Lighthouse. Watching the piercing orange and purple colours light the sky by the cliffside lighthouse is a magical sight. The cozy town of Bar Harbor serves as the gateway to Acadia National Park and is where I spent the evening. You’ll find boutique hotels, charming B&Bs, and other relaxing accommodations for a restful sleep.

In case you find yourself with some extra time on your hands or maybe the whale watching at Cape Cod gave you a teste for more, Bar Harbor also has great whale watching opportunities. There are lots of places for whale watching in Maine but Bar Harbor is where I would recommend you to head out from.

Day 14 – Acadia National Park (ME) to Boston (MA)

Acadia National Park was a thrilling destination to conclude my road trip, and it was time to head back to Boston. Logan International Airport is about 260 miles from Acadia, but the ride is spectacular. A portion of the route follows the wild Maine coast and makes you want to stop every few miles. You made find this hard to believe, but Maine has more coastline than California. With its rocky coast, sandy beaches, beautiful lighthouses, Maine’s 3,478 miles of coastline are a national treasure.

The bulk of your journey is along I-95 South, and you’ll have the chance to visit several adorable towns. U.S. Route 1 South is an alternative that’s slightly closer to the coast, but you’ll increase your drive time. My advice is to stick to the interstate unless you have plenty of hours to spare. The last thing you want is to rush to return your vehicle and catch a flight. If you’re itching to stop at some Maine coastal towns, Camden is the first one I’d suggest driving from Acadia National Park. Although you’ll need to take Route 1, it’s one spectacular town where the mountains meet the sea.

Just south of Portland, Old Orchard Beach is a classic stop for beach lovers in Maine. It’s a great stop on a summer road trip with a fun-filled boardwalk, sandy shores, and New England’s only beachfront amusement park. Kennebunkport is another quaint town with gorgeous cottages, stunning beaches, and a lively harbour. Other delightful stops before you exit Maine include Ogunquit, York, and Kittery.

Depart Logan International Airport

Your New England road trip comes to an end, and it’s time to return your vehicle to Boston. If you rented your car from downtown Boston, the rental agency might let you return it at the airport. My advice is to ask the agent beforehand if airport drop off is allowed and if there’s a fee. You’ll know in advance where you’re able to return the vehicle and plan your departure accordingly.

I hope you enjoyed this 14-day New England road trip itinerary. If you have any questions or recommendations, leave a comment below!

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2-Week New England Itinerary: The Perfect Fall Foliage Road Trip

I’ve always wanted to explore the New England states, especially after I moved away from the northeast to Seattle. Fall was my favorite season as a kid. I’d crunch through the fallen leaves with my old-school film camera and try to capture the fall colors. I know Pennsylvania isn’t known for its fall foliage like other states, but it was what I knew and looked forward to year-after-year.

Below is a rough New England itinerary for a fall foliage road trip to follow if, like me, you want to visit and tick off the states in the upper righthand corner of the United States.

Flying into New York, I arrive late into JFK and pick up my rental car. From there, I drive to Stamford, CT for a quick hotel stay to sleep before the travel begins. I used points for the hotel which was just off the highway.

Driving time: JFK to La Quinta Inn & Suites Stamford – 50 minutes

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Day 1: Connecticut, Rhode Island, and Massachusetts

I was excited to visit a couple of towns with early U.S. history, like Boston. Andy chooses to sample the local coffee shops while working remotely as I go by foot to explore the cities.

Driving time: La Quinta Inn & Suites Stamford to New Haven, CT – 55 minutes

Connecticut: New Haven – a few hours

I’m a huge fan of Gilmore Girls and couldn’t pass through Connecticut without visiting Yale University. After a cup of Koffee , I wander through the campus and even was able to pass through a student only gate into a courtyard.

I marvel at the old brick buildings and buy postcards at the college bookstore. It feels like any other college town with students walking the sidewalks around a business district. Unfortunately, the Yale University Art Gallery is closed on Mondays, which was high on my list. After a couple of hours, I return to the car and meet Andy to drive to the next stop.

Driving time: New Haven, CT to Providence, RI – 1 hour and 45 minutes

Rhode Island: Providence – a few hours

As the lunch hour approached, Andy and I stop for a bite to eat. Sampling local Rhode Island beer as we eat brunch and plan where to go in Providence. After some discussion, we decide to see the Rhode Island State House. I take pictures as we walk around the outside. After, we stumble into the Roger Williams National Memorial and learn about the 1636 settlement.

Where to eat: Julian’s

Driving time: Providence, RI to Boston, MA – 1 hour

Boston – half day

After checking into the hotel, I left Andy to finish work before dinner as I planned to walk the 2.5 miles of the Freedom Trail. The one end starts at Boston Common Visitors Center, a perfect place to stop for another postcard collection. As I made my purchase, a tour guide does a last call for the 4:30 pm tour. Perfect timing! I join the 90-minute tour for $14 and learn more history than I could have walking the brick trail myself.

John wears a full costume and takes us through the history up until the Faneuil Hall Marketplace. I plan on the second half for tomorrow with a discount if I join the tour from Faneuil Hall. I decide to walk the trail more myself since rain is on the forecast for tomorrow to see Paul Revere’s house. After, the trail is under construction as dinnertime approached, so I detour back to the hotel.

Where to eat: Tip Tap Room Where to drink: Beerworks Where to stay: Courtyard by Marriott Boston Downtown

Day 2: Massachusetts and Maine

Today, Andy works in the morning while I explore Boston before heading to Maine to meet up with some family.

After an early breakfast at Boston Public Market, I pick up the Freedom Trail on the Charlestown Bridge. My first stop was the USS Constitution. I arrive 15 minutes before opening and go through security to tour the boat. U.S. stationed military personnel staff the boat and are standing up high on the sails. I walk around the boat and overhear some of the history from the staff on the ship before continuing my way before the rain starts.

I finish the Freedom Trail at Bunker Hill Monument and climb the 294 stairs to the top for views of Boston. After, I walk back towards the hotel and pass Copp’s Hill Burying Ground and Old North Church as the rain starts.

I dip into Bova’s to pick up a Boston Cream dessert and meet up with Andy at the hotel for late check out. We eat a late lunch at Regina Pizzeria before continuing the road trip to Maine.

Where to eat: Inna’s Kitchen, Bova’s, Regina Pizzeria

Driving time: Boston, MA to West Bath, ME – 2 hours and 45 minutes

Bath, ME – 1 night

We arrive at my Dad’s cousin’s house outside of Bath, Maine. Andy joins a trip to the store to pick out the fresh lobster for dinner. Jim grew up in Maine and provides tips at dinner for how to find all the meat on the lobster for my parents and me. Barb takes my mom and I to the local yarn shop and drives us through the town of Bath. The rain deters us from getting out and walking inside the shops.

Where to eat: Anywhere with seafood Where to stay: Airbnb or hotel

Day 3: To Acadia National Park, Maine

The point of the trip to New England was Acadia National Park. I go out of my way to visit national parks when possible and couldn’t wait to explore a new national park for a couple of days.

Adding to Andy and I, my parents and Barb and Jim head north to Acadia National Park. The rain continues in the morning giving us an excuse to sleep in and cook breakfast.

Instead of driving the highway, we navigate U.S. 1 through small coastal towns, stopping for lunch for a lobster roll, and realizing I continued to state each town was “cute” as we pass through.

We meet at the campsite and have some wine before going out to dinner. After, we go on our separate ways and go to bed early.

Where to eat: Hill’s Seafood Co., Rockland, ME and Cafe Dry Dock & Inn

Driving time: West Bath, ME to Seawall Campground, Acadia National Park via U.S. 1 North – 3 hours

Day 4: Acadia National Park, Maine

The second day, we cook breakfast on a campfire and then leave to Hulls Cove Visitor Center. From there, Dad, Andy, and I decide to hike up Beehive while the other explore less elevated trails.

Hiking map: Beehive to Bowl Trail

After the hike, we rejoin the others at Thunder Hole before stopping at Otter Cliffs lookout. The last stop requires a drive to the highest point of the park: Cadillac Mountain. We explore the slab rock on the summit after battling the other cars for park spots. I’d hate to see it on a weekend!

We make plans to meet at Bass Harbor Head Lighthouse around 5 pm. The lighthouse is beautiful and the sun dips behind a layer of clouds before sunset. We all return to the campground for pork chops cooked on the fire.

Where to eat: Campground Where to stay: Seawall Campground or Harbor View Motel & Cottages

Day 5: To Baxter State Park, Maine

We say goodbye to the family and continue to the next destination. Before leaving Southwest Harbor, we stop at a coffee shop to connect to Wi-Fi and download directions to Baxter State Park. On the way to inner Maine, we stop at Bangor for more hiking supplies and brunch.

We check into the park and pay the entrance fee. Abol Campground is where we’ll be camping for the night. Down by the river, I set up camp in my very first lean-to. I buy a bundle of wood from the ranger and talk to her about our hiking plans.

We cook dinner next to the fire and enjoy the crackling and warmth before heading to bed early to wake up early.

Where to eat: At campsite Where to stay: Abol Campground, Katahdin Stream, or Roaring Brook

Driving time: Seawall Campground, Acadia National Park to Abol Campground, Baxter State Park, ME – 3 hours and 20 minutes

Day 6: Baxter State Park, Maine to White Mountains, New Hampshire

After a decent chunk visiting Maine, today is the last day before heading to New Hampshire. A part of me wants to stay in Maine because I know the leaves aren’t at their peak levels but am eager to visit a new state and high point. Though, first, I have to hike to the top of Maine.

Driving time: Abol Campground to Roaring Brook Campground, Baxter State Park, ME – 45 minutes

Baxter State Park – early morning and afternoon

The second day we climb to the top of Mount Katahdin, the highest peak in Maine. The moody weather kept us hiking fast as we questioned the decision for hiking the 1-mile Knife Edge ridge section with 35+ mile wind gusts moving misty clouds over the mountain’s crest. Read more about summiting Maine’s Mount Katahdin via the Knife Edge route.

Hiking map: Helon-Taylor to Knife Edge to Chimney Pond

Where to eat: On the trail Where to drink: Baxter Brewing, stop along the drive

Driving time: Roaring Brook Campground, Baxter State Park, ME to Crawford Notch State Park, NH – 5 hours and 50 minutes

White Mountains – late evening

After the 7.25 hour hike, we change and begin to drive making a pit stop at Baxter Brewing Company outside of Augustus. Before checking into the campground, we stop in North Conway for a bite to eat. Exhausted, we arrive at camp, set up, and go to bed eagerly.

Where to eat: Muddy Moose Restaurant & Pub Where to stay: Dry River Campground – Crawford Notch State Park

Day 7: White Mountains, New Hampshire

Mount Washington has been on my list for years. Andy did a winter ascent several years ago, and I’m elated to visit New Hampshire for the first time.

Known for record-breaking winds, I anticipated a similar hike to Katahdin the day before. Andy works from a local coffee shop in Conway, and I spend the day hiking to the summit via the Huntington Ravine Trail to Tuckerman Ravine Trail loop .

Hiking Map: Huntington Ravine to Tuckerman’s Ravine Loop

Where to eat: Moat Mountain Smokehouse & Brewing Company Where to stay: Dry River Campground – Crawford Notch State Park

Driving time: Crawford Notch State Park, NH to AMC Pinkham Notch Visitor Center, NH – 1 hour and 4 minutes round trip

Day 8: Burlington, Vermont to Adirondacks, New York

Being so close to Vermont, we needed to do something notable to count it as a state visited.

Driving time: Crawford Notch State Park, NH to Burlington, VT – 2 hours and 20 minutes

Burlington, Vermont – few hours

Deciding to break up the drive, we stop in Burlington for a few hours to work remotely and grab lunch. The drive was beautiful with farms scattered along the rolling mountains. The leaves just starting to turn to their festive colors. Before leaving town, I stop at a small shop to pick up maple candies.

Next, we drive to a small town of Charlotte to board the ferry across Lake Champlain to Essex, New York.

Where to eat/drink: Zero Gravity Brewpub at American Flatbread Where to work: Fletcher Free Library

Driving time: Burlington, VT to Adirondak Loj & Heart Lake Wilderness Campground – 2 hours depending on ferry schedule

Adirondacks, New York – evening

The overcast skies make the fall foliage look dull even though they were the best I’ve seen on the trip so far. Crossing the lake, we enter New York and drive to the campground to check-in. After setting up camp and upgrading to the lean-to, we make a supply run in town to pick up food to cook and beverages.

Where to stay: Adirondak Loj at Heart Lake or Wilderness Campground at Heart Lake Where to buy local alcohol: Terry Robards Wines & Spirits

Day 9: Adirondacks, New York

With plans to rock climb and hike to see the fall foliage, I am excited to see the many lakes and rolling mountains. Now, I just need sunshine in the forecast, which did not look promising.

Unfortunately, rain decides to change the plans. I spend the day working from the public library in Lake Placid with a whopping half inch forecasted throughout the day.

Where to eat: Big Slide Brewery & Public House – probably the best food of the trip with decent beer. Where to stay: Adirondak Loj at Heart Lake or Wilderness Campground at Heart Lake Where to work: Lake Placid Public Library

Driving time: Adirondak Loj & Heart Lake Wilderness Campground to Lake Placid, NY – 32 minutes round trip

Day 10: Adirondacks, New York

Mount Marcy is the highest peak in New York state with the trailhead leaving from Heart Lake. All I had to do was roll out of my sleeping bag, put on my hiking clothes, eat a little breakfast, and start hiking. The fog lingers in the valleys and the rain from the prior day make the hike a little more adventurous. We hop from stone to stone to keep our feet dry from the water streaming down the trail. One river crossing didn’t have a high water bridge, so we remove our socks and boots to ford the high water.

Hiking map: Mount Marcy via Van Hoevenberg Trail

Driving time: Adirondak Loj & Heart Lake Wilderness Campground to Beacon, NY – 3 hours and 50 minutes

*Days 11-17 were spent visiting friends and family in various parts of Pennsylvania.

Day 11: Beacon, New York

Similar to the Adirondacks, the first planned day of climbing is canceled with flash flood warnings and up to an inch of rainfall. Time to slow down and let the weather prompt a work day, at least for Andy. I take a few hours to casually stroll through the Dia:Beacon art museum. Filled with sculptures and abstract installations, I’m happy to go solo. Museums, for me, are best experienced alone.

Where to stay: Airbnb or with friends Where to eat: Draught Industries

Day 12: Shawangunks, New York (The Gunks)

Rock climbing at the Gunks in the fall is something that has always been in the back of my mind. Even with the heavy rainfall the prior day, my local friend assured the rock dries fast. We pay the $20 per person climbing fee for a day of adventure.

Driving time: Beacon, NY to Gunks parking area – 40 minutes

Traveling to climb always has me testing out the local ratings by not pushing grades, so my first choice was a 3-pitch climb called Gelsa. The higher pitches are covered by a trickling waterfall, so we opt not to attempt it. Instead, we walk further down the wall and begin to climb the 4-pitch Yum, Yum, Yab Yum. Both climbs on the less-crowded Near Trapps area.

After climbing the route, we walk over the bridge to scope out the Trapps walls and look to climb Three Pines, also wet. It is late in the day and we decide to head to New Paltz for some after climbing brews before visiting friends and eating dinner.

Where to drink: Arrowood Outpost

Driving time: Gunks to New Paltz to Milton to Beacon – 1 hour and 10 minutes

Day 13: Beacon, New York

Fingers crossed with 40% of rain forecasted and the rain volume amount to be low, we pack the climbing gear. Do we drive 40 minutes and pay another $20 per person to maybe climb one route? The sole-crushing answer is no.

Instead, Greg, the friend we’re staying with in Beacon, introduces us to the most popular hiking trail , Breakneck Ridge, in the United States. I am skeptical as I never heard of the trail before, so how is it popular? Maybe it should be called the most populated trail. Why? Because the trailhead starts close to a major train stop from New York City in the Hudson River Valley.

The short trail navigates over rocky terrain to the point where using hands to scramble is required. Really, new hikers are swarming here? The trail consists of many benches. We make a loop out of the hike to avoid going down the wet rocks and have the trail to ourselves as the rain soaks our non-Gore-Tex layers. As we finish the hike, the rain ends and the rest of the hikers emerge.

Hiking map: Breakneck Ridge to Breakneck Bypass Trail loop

After, the three of us head to Cold Springs to warm up over a second cup of coffee and empanadas to snack. Walking through the tourist town, I can see why it is a popular weekend getaway from The City.

Unfortunately, the road trip has come to an end, and we drive to the airport to close the loop.

Where to eat: Rincón Argentino

Driving time: Beacon, NY to JFK airport – 2 hours

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The Grand Tour of New England

15 days, 14 nights

If time allows and it is your first visit to New England, a self driving road trip tour covering all six New England states will allow you a true taste of the region and all of its beauty and diversity. After leaving Boston, you will find wide open spaces, a friendly and hospitable welcome, and wonderful accommodations. Your hosts and innkeepers will serve as local sightseeing guides pointing you toward those perfect places to enjoy the scenic beauty of New England.

                                                       Explore More Road Trips & Itineraries

Day 1 — Boston, Massachusetts

Most international visitors arrive in New England at Boston’s Logan Airport . Conveniently located just three miles from downtown, Logan’s international terminal allows for a speedy transfer through customs and immigration and into the city. There are a variety of ways to get into the center of Boston , including public bus, subway and taxi.

Remember not to rent a car until you are heading out of the city — you will not need a car in America's “Walking City” and parking fees downtown are particularly expensive. Most rental car companies will allow for downtown pick up or failing that, the short journey back to Logan Airport is worth it on your day of departure from the city. Boston is the capital of Massachusetts and the unofficial capital of New England. A sophisticated and charming city, it is relatively small and walking is the best way to get around. Many international visitors feel very comfortable in Boston as it is the most 'European' of all American cities, with distinct small neighborhoods such as the North End , filled with lively Italian restaurants and cafes; the Back Bay, where wonderful shopping streets are filled with every designer shop imaginable; and Beacon Hill, with its cobbled streets and brown brick townhouses. Spend at least two nights in Boston to get the best feel for the city.

Places to stay in Boston

Day 2 — Boston

Spend the day exploring Boston’s unique history and locale. Here are some ideas to get you started:

• Walk the Freedom Trail.  A great way to easily see a lot of the city, the Freedom Trail links 16 places of historic interest throughout the city. You can begin anywhere along the route, but it is easiest to begin at Boston Common where the Visitor Center is located.
• Take A Duck Tour. The "Ducks" are amphibious vehicles that are able to travel both in water and on land. Boston Duck Tours  offer a wonderful perspective of Boston and Cambridge: see the skyline from the Charles River and hear about the unique sights of the city from your Boston driver!
• Other great ways to see the city include Trolley Tours , which allow you to hop on and off the trolley, or a cruise on Boston's beautiful harbor .
• Tour Fenway Park. Fenway is America’s oldest baseball park, home of the iconic Green Monster. Tours of Fenway Park are offered year-round, and if you visit during baseball season (April to September), you can also catch a Red Sox game.
• Consider putting aside some time to visit some of Boston's rich cultural gems, such as the JFK Library , the impressive Museum of Fine Arts , and a favorite for kids, the New England Aquarium .

Day 3 — Boston to the Maine Coast

Leave Boston today to begin your road trip and head north up the coast and into Maine . Time allowing, you should stop and visit any one of the wonderful small towns on the coast . Salem, Mass. , is known for the infamous Salem Witch Trials and is home to the amazing Peabody Essex Museum , whose collections include art and cultural artifacts from all over the world. A little farther north is the pretty artist colony of Rockport. A helpful note: most highways in New England have speed limits of 55-65 miles per hour (90-105 km/h).

The rugged state of Maine is as big as all the other New England states put together; on this tour, you will explore a little of its spectacular coast. Picturesque fishing villages are nestled together along a dramatic coastline. Don't forget to sample some of Maine's fine culinary delights — lobsters and blueberries! You may prefer to stay in the southern coastal areas, in the beautiful coastal towns of York, Kennebunkport, and Ogunquit, or continue north to Portland, a lively port town with a rich historic and cultural heritage and a budding culinary scene.

Search for accommodations in: Portland, Maine • Ogunquit • York • Kennebunkport

Day 4 — The Maine Coast

Spend the day exploring the coast of Maine: a visit to Portland with its many small galleries, shops, restaurants and museums, is a treat for city-lovers. Maine’s smaller, coastal beach towns are especially popular for their family-friendly sandy beaches, fresh seafood and relaxed atmosphere. For a quintessential Maine experience, take a lobster boat ride from Perkins Cove in Ogunquit, or stop by one of the many lighthouses along the coast, such as the Nubble Light in York or the Portland Head Light . Many fine small museums that scatter the coast, like the Wells Auto Museum and the Ogunquit Museum of American Art . Freeport, Maine, is also a good day’s stop for outlet shopping in a beautiful New England village.

Day 5 — Maine to the White Mountains of New Hampshire

Today, drive west through Maine and into New Hampshire's White Mountains region .  The drive will be longer today as there are no major highways to take you east-west in this part of New England. In New Hampshire, beautiful shimmering lakes and high mountains dominate the landscape, as the road winds through pretty villages. A paradise for hikers in the summer and a playground for skiers in the winter , the scenic White Mountains provide the perfect backdrop for outdoor recreation or quieter relaxation. A day of traveling can end on a high note with a trip to the top of Mount Washington , the tallest mountain in New England (6,289 ft / 1,917 m). In the summer, you can get to the summit on foot, by car on the 8-mile toll roador via the Cog Railway on a steam train. In the winter, the auto road can still be traveled, but only on a snowcoach tour.

Day 6 — New Hampshire

Spend the day exploring northern New Hampshire . A wonderful tour for driving follows the Kancamagus Highway between Lincoln and Conway, one of the most scenic in the USA. It also offers a chance to visit the Flume , a natural granite gorge with wooden walkways and rushing waterfalls. If souvenir shopping is on your list, New Hampshire is also tax-free and North Conway is one of the premium outlet shopping areas in the region. You can also travel a little further south into the Lakes Region of New Hampshire . Lake Winnipesaukee, the largest lake, offers everything from great sailing and fishing to relaxing water cruises on paddleboats.

Find lodging in New Hampshire

Day 7 — into vermont's green mountains.

Continuing the tour westwards, Vermont is the next stop. The Green Mountain State is known for its pristine landscape, rolling hills and the romance of small communities where white church spires poke up between the mountains. There are many lovely places to stay in Vermont, and you can choose to stay in the northern , central or southern part of the state. You will have the opportunity to experience the twisting country roads, mountain views, small towns, art galleries, country stores, locally-grown food and working farms throughout the state. One suggested stop in Vermont is the the state capital city, Montpelier. It is the smallest state capital in the country with just 8,000 residents. The town looks like one you might have seen in the movies, and is dominated by the gold-leafed dome of the Vermont State House. Continue on to Waterbury and take a unique factory tour at the Ben & Jerry's Ice Cream Factory and then onto Stowe , a charming mountain resort town nestled at the foot of Mount Mansfield.

Day 8 — Vermont

On your first full day in Vermont, make time for a visit to Burlington , Vermont's largest city. Many points in town offer beautiful views of Lake Champlain and the Adirondack Mountains in New York. Burlington’s large student population gives it a great "buzz" — nightlife, restaurants and music halls are busy year-round. A pedestrian-only shopping street, Church Street , is the heart of the city with a mix of local and high-end boutiques, restaurants and bars. Burlington is also an ideal place to sample some of Vermont’s famous craft beer. Spend the night in Burlington, or get a head start on the next day’s travel by heading south. Route 100, the “Skier’s Highway,” winds down the spine of the Green Mountains, past ski resorts, lakes, and gorgeous views, with plenty of opportunity to stop for the night in quaint Vermont towns.

Find places to stay in Vermont

Day 9 — Vermont to The Berkshires, Massachusetts

From Vermont, head south and into the lovely Berkshire Mountains of western Massachusetts . Charming Stockbridge is the heart of a region packed with culture and charm. In summer, the hills are a hot spot for musical talent, as the Tanglewood Music Center becomes home to the Boston Symphony Orchestra. Summer theater and dance performances are abundant, as is cutting-edge modern art at Mass MoCA and fine art at the world-class Clark Institute in the lovely college town of Williamstown.

Search for lodging in the Berkshires

Day 10 — to connecticut.

Continue your journey southwards and into Connecticut . Stretching east from New York City, Connecticut’s varied landscape includes wooded hills, rural farmland, rocky shores, and wide beaches. Many areas have beautifully preserved clapboard homes set amidst well maintained villages like Essex and Chester .

Travel south until you hit the coast of Connecticut, where there are many small towns that are worth exploring. Mystic is a good choice for a stop. Visit the Mystic Seaport , a living history village with working craftsmen, the world-class Mystic Aquarium or the Mashantucket Pequot Museum , which depicts Native American life in southern New England.

Search lodging in Connecticut

Day 11 — newport, rhode island.

A must on any visit to New England, Newport is as famous for its seaport history and Gilded Age mansions as its superb summer festivals. The cliff top mansions are truly magnificent homes, many built by the wealthy industrialists of the nineteenth century as a place to escape the summer heat of New York City. Beautifully preserved, you can tour 11 of these historic homes from different periods in American history. Save time to stroll along the Cliff Walk , with great views of the ocean, or to enjoy the downtown fun of Newport.

Places to stay in Newport, Rhode Island

Days 12-14 — cape cod, massachusetts.

A perfect way to end your visit to New England is to stay for a few days on beautiful Cape Cod . Base yourself in any one of the charming small towns and villages along the Cape and enjoy spectacular beaches, museums, music festivals, antique stores, sailing, great golf courses, and whale watching. Spend a couple of days in Cape Cod, enjoying the beaches, sun and sand on the high dunes and long beaches of the National Seashore . You can also explore the small towns and villages of Cape Cod, characterized by beautiful clapboard architecture, faded to a dusky grey from salty air. From spring until autumn, you can take a whale watching boat tour from many parts of New England — the feeding grounds for the humpback and finback whales are found just 30 miles (50 km) off the Massachusetts and New Hampshire coasts. These magnificent creatures played a huge role in New England's history: the whaling industry flourished here. Today, whales are protected but the history of whaling in New England can be seen at several area museums. A day trip to Martha's Vineyard or Nantucket is an option as well — ferries to the islands run year-round, though passages are more frequent in the summer months. The best way to explore the beautiful island landscapes is on a bike. Nantucket Town is a sight to see, thanks to its Georgian houses, old-fashioned street lights and brick pavements. Martha's Vineyard is closer to mainland Cape Cod, and a little larger, with several distinct and interesting towns. Both islands have great shopping, lovely sights, and the freshest seafood you can get.

Find lodging in Cape Cod, Martha's Vineyard and Nantucket

Day 14 — Cape Cod & Plymouth

History enthusiasts, don't leave New England without a trip to Plymouth, Massachusetts, and the Plimoth Patuxet (formerly the Plimoth Plantation). Plymouth is where the first Pilgrims settled back in 1620 after first landing in Provincetown. Plimoth Patuxet is a recreated Pilgrim settlement, where costumed interpreters work, eat and speak as the 17th-century colonists did while Native Americans demonstrate traditional methods of building homes and canoes.

Day 15 — Boston for Departure

Cape Cod is approximately a two hour's drive from Boston (depending on your exact location on the Cape), so depending on your flights, you may want to relax on the beaches of the Cape this morning or start the day in Boston. After a grand tour of this size, a leisurely morning is just the ticket.

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A Family Road Trip Through New England

March 1, 2022 //  by  Gwen Engler //   Leave a Comment

“Mommy, can you tell me the story of our vacation?”

Even now, six months later, this is a frequent refrain in our house. Our three-year-old, E, loves to be told stories, and one of his favorites is when we recount a play-by-play of our very first vacation together: a family road trip through New England. 

I tried to go into this trip with low expectations, since I had no idea how traveling with a 2.5-year-old and five-month-old would go. Thankfully, our vacation blew any of those expectations out of the water. We had the most wonderful time seeing a gorgeous part of the country and spending time as a family, so much so that my son still loves talking about it almost half a year later.

Today, I want to share a day-by-day breakdown of our itinerary, along with all the tips and resources you’ll need to plan your own incredible family road trip through New England! 

New England Family Road Trip: At a Glance

Day 1:  Bristol and Newport, Rhode Island Day 2:  Bristol to North Conway, New Hampshire, via Boston Day 3:  Echo Lake State Park Day 4:  The Mount Washington Cog Railway Day 5:  North Conway to Jefferson, Vermont, via the Kancamagus Highway Day 6:  Smuggler’s Notch State Park Day 7:  Burlington, Vermont

Day 1: Bristol and Newport, Rhode Island

Because we didn’t arrive in Bristol until after 1:00 AM the night before, we didn’t exactly spring out of our Airbnb on our first morning in Rhode Island. That suited us fine, as family time was the name of the game. It also allowed us to have a tasty breakfast on the lovely back patio.

M picked up takeout from Bristol Sunset Cafe , which was recommended by our hosts and certainly lived up to the hype. Their breakfast sandwiches (particularly the So Good sandwich I ordered) were delicious and the perfect start to our day.

Thus fueled up, we got ourselves together and set off for Newport.

Newport is located on an island in southern Rhode Island and is a pretty quintessential coastal New England town. It rose to prominence as a summer resort town for some of the wealthiest families in the United States (do names like Vanderbilt, Astor, and Kennedy ring any bells?) and is still home to some outrageously large and opulent mansions. The town is also a mecca for sailing enthusiasts: the National Sailing Hall of Fame is here, as were fifty years’ worth of America’s Cups. Today, it’s a beautiful seaside town with lots of offer.

As soon as we decided to add Rhode Island to our itinerary, I knew Newport would make the perfect first stop. And it was! We parked in the lot at Easton’s Beach, a long and narrow strip of sand fronting a U-shaped bay, and set off for the famous Cliff Walk . 

The Cliff Walk is a 3.5-mile National Recreation Trail along Newport’s rocky coastline. On one side you have the Atlantic; on the other you’ll pass huge Gilded Age mansions.

We didn’t quite make it to any views of mind-blowing mansions, since we started at Memorial Boulevard and only made it as far as the Forty Steps at Narrangansett Avenue, but it was still a beautiful walk. The sky was a cloudless blue and the views out over Easton Bay were just lovely.

Despite E’s little legs getting tired and having to change a blowout diaper in the grass, the Cliff Walk was really enjoyable. Perhaps even more enjoyable, though, was returning to Easton’s Beach and grabbing lunch at their snack bar . 

We had heard great things about the snack bar’s lobster rolls, so we placed an order and sat on the seawall enjoying the warm sunshine while we waited.

When our order came up, we snagged a picnic table in a nearby pavilion and tucked in. Sitting there, eating delicious lobster rolls with the sea breeze on our faces, we felt like we were truly in New England. 

By that point, the kids were ready for a bit of rest. We headed back to the Airbnb – another big departure from M’s and my standard pedal-to-the-metal operating procedure! – for a little downtime. Later that afternoon, at our hosts’ recommendation, we took a short drive into downtown Bristol for a delicious dinner at Quito’s Seafood Restaurant and Bar .

Quito’s is located right on the water in Bristol Harbor, and the sun setting over the various yachts and sailboats was just beautiful. 

The food was awesome, as well; when we asked which of their seafood soups, chowders, and bisques we should try, our server told us that the lobster bisque was – and I quote – “insane.”

I mean, that has to be your choice then, right?

Turns out he was right. The bisque was so tasty and had massive chunks of lobster meat throughout.

M and I also each had a Sicilian spinach salad and split an order of fried clams. I was in heaven. (There was chocolate milk and a whole cup of crayons to accompany his meal, so E was happy, too.)

By the time we left, the sun had disappeared below the horizon and the harbor and adjacent park were bathed in evening light.

With such a great first day under our belts, we were starting to feel confident that this whole family vacation thing could be a really great experience. Thankfully, it just kept getting better.

Tips for Bristol and Newport with Small Children:

• Although it was a very late night, we were really glad that we made the first long drive of our family road trip at night when the kids had a good chance of sleeping most of the way. It was nice to be able to just wake up in Rhode Island and get the vacation started!
• We took the stroller on the Cliff Walk but should have taken our baby carrier as well. E’s little legs got tired and it would have been easier to put him in the stroller and wear S instead of the other way around.
• Parking at Easton’s Beach is no joke; it cost us $25 for the pleasure of leaving a car there. We sucked it up and paid the price, since it was the closest we could get to the Cliff Walk and we wanted to try the lobster rolls at the snack bar, but if we didn’t have the kids along I probably would have tried to find parking elsewhere. 

If you have older kids or more time...

• Stroll the downtown area. There are lots of beautiful shops and restaurants.
• Visit some of the mansions along the Cliff Walk and beyond. Perhaps my biggest regret about our time in Newport was that it didn’t work for us to visit The Breakers in particular.
• Spend some time on Easton’s Beach.

Day 2: Bristol to North Conway, New Hampshire

Our stay at Gloria’s Getaway was so comfortable and our time in Rhode Island so enjoyable that we were reticent to leave after just one day. I had been less excited about Gloria’s compared to the other Airbnb’s we’d be visiting on this trip, mostly because it was a straightforward, homey apartment versus the mountain condo and rustic cabin we’d be staying in later. But in the end it completely won us over and was probably our favorite place that we stayed on the trip.

The whole apartment was spotlessly clean and our hostess, Mary, had added so many thoughtful touches. Not only had she handcrafted a local guide, but she was super responsive and hospitable. We felt so at home that it was hard to pack up and leave!

Thankfully, we had the promise of brunch with M’s cousin’s family outside Boston and the White Mountains waiting for us later that day. We said goodbye to Gloria’s Getaway and headed north.

Most of our morning and early afternoon were spent visiting with M’s cousin Jess and her family outside of Boston, and then we continued on toward North Conway, New Hampshire. I had planned to stop in Portsmouth, NH, to break up the drive, but the kids both passed out immediately and were still fast asleep as we approached the exit. Thus, M and I decided to press on to North Conway and were able to enjoy a quiet drive north.

North Conway is pretty little town that serves largely as a tourist base for exploring the nearby – and stunning – White Mountains. We arrived with some time to spare before we could check into our next Airbnb, so we let E blow off some energy at the Harvey Dow Gibson Playground along the main drag through town.

To his delight, we also arrived on the last day of the Mud Bowl , an annual event that benefits local charities. Seeing people playing football in ankle-deep mud and muck made such an impression on E that he was still talking about it weeks later.

At last, we made our way out of town to our Airbnb , which was a three-bedroom condo tucked away in the woods off the highway.

Our hosts had clearly done a lot of work to update the place and turn it into a cozy mountain retreat. There was plenty of living space and three bedrooms that allowed us to spread out.

We kept it low-key that night with dinner at Moat Mountain Brewing Company (the grilled chicken and portobello sandwich was *chef’s kiss*) before turning in for our first sleep in New Hampshire!

• We were fortunate to get to see family while on this trip, but we could have just as easily popped into Boston for a few hours on our way from Rhode Island to New Hampshire. At roughly a third of the way through the drive, it would make a great stopping point. (Though, to be honest, there’s so much to do in Boston that a few hours might just be a tease!)
• As I mentioned, we also had planned to spend some time in the seaside town of Portsmouth, New Hampshire, which would be a worthy alternative

Day 3: Echo Lake State Park

One of the major goals for this first family vacation of ours was to spend as much time as possible outdoors. Not only were we headed to a beautiful area of the United States, but getting outside would provide some low-cost fun while also giving E plenty of opportunities to burn off all that toddler energy. 

Our first full day in New Hampshire provided us with the perfect setting for our first hike as a family of four: Echo Lake State Park . 

Echo Lake was perfect for us because it:

• is located less than two miles off Route 302, the main road through North Conway;
• features a flat, .8-mile-long loop trail around the eponymous lake that was the perfect distance for our toddler; and
• was stunningly beautiful.

We were fortunate to have a gorgeous, blue-sky morning on the day we headed to Echo Lake. After paying our entrance fee, parking, and changing what felt like our thousandth diaper blowout of the trip thus far, we hit the trail. First, we passed through a nice picnic and recreation area, where we certainly would have enjoyed a packed lunch if we’d brought one.

It didn’t take long before we were in full view of Echo Lake and the massive rock faces that make it so scenic.

A wide stretch of sand led down to the calm, blue-green water. 

The trail looped around the lake, sometimes hugging the water’s edge but mostly leading through the forest. 

Whether by design or the work of visitors, there were also numerous offshoot paths cutting down to the water at various points along the way. E, of course, wanted to take each one for a new opportunity to toss sticks and/or stones into the lake.

At last, to E’s delight, we reached the main recreation area and allowed him to run squealing into the lake. It was a little chilly, and we hadn’t brought a swimsuit, but he had a blast splashing and swimming around in the calm, shallow water. The rest of us, meanwhile, basked in the bright sunlight and the incredible scenery.

By the time we got E dried off and changed into his spare set of clothes, we were all pretty hungry. We drove the short distance back into town, grabbed takeout from the scrumptious Stairway Cafe , and returned to our home base for naptime. Thanks to the exertion of the hike and the excitement of his impromptu swim, E slept like a log. 

Tips for Echo Lake State Park with Small Children

• On a warm day, be prepared for the kids to take a dip in the water. There are nice bathhouse facilities near the park entrance where you can change clothes and diapers.
• At the time of writing, entrance fees for the park were $4 per adult and $2 for each child aged 6-11. 
• While we drove right in, the park can fill up on nice weekends and holidays, so consider booking your entrance in advance via the state park website . 

If you have older children or more time...

• Try one of the longer and more scenic hikes. I’ve read that Cathedral Ledge (also its own state park, but hikable from Echo Lake) is particularly stunning.
• In good/warm weather, spend a few hours at the little beach.
• Take some time to walk the main drag through North Conway (White Mountain Highway, or Rt. 302). There are lots of great restaurants, shops, boutiques, and other places to explore and fill a couple of hours.
• Just outside of town, and not far from our Airbnb, is a family amusement park called StoryLand , which also has an aquarium onsite. Both were recommended to us for a return visit.

Day 4: The Mt. Washington Cog Railway

Our second day in New Hampshire just might have been the best day of E’s short life thus far. Within a 12-hour span, he got to ride a train, eat lunch overlooking a golf course, play miniature golf, and eat a giant dessert. 

I mean, what more could a 2.5-year-old golf and machinery aficionado want?

But I’m getting ahead of myself. Let’s start at the beginning, when we loaded up the car and made the 45-minute drive through the White Mountain National Forest to the Mount Washington Cog Railway . 

The Mount Washington Cog Railway is a three-mile rack-and-pinion railway that climbs all the way to the top of the tallest mountain on the US East Coast. Not only is it incredibly scenic, ascending through the tree line with views of the gorgeous White Mountains all around, but it’s a mechanical marvel and a piece of history. Although you can hike or drive up Mount Washington, there’s no doubt that the railway is the most charming and memorable way to reach the top.

Visiting the Cog Railway is one of the most popular things to do in New Hampshire, and we thought it would make a great activity for our machine-obsessed 2.5-year-old. Our train tickets were actually the only activity we booked in advance for the entire trip, and we’re very glad we did. We were able to get seats at the very front of the train, and fortuitously had chosen the left side, which seemed to be a bit more scenic than the right.

It wasn’t long after M and I got the two of us settled with a kid on each lap that the train chugged into motion and began its ascent.

I wrote a full account of our journey on the Mount Washington Cog Railway in another post, so this recap will be a bit abbreviated. But suffice it to say that this trip was well worth the price of admission for the scenery alone!

The views from the upper portions of the railway were stunning. The trees fell away to reveal green mountains rolling off into the distance, stretching all the way into Vermont and Quebec before disappearing into the horizon.

At last, we reached the summit and emerged from the train into a chilly fog. This wasn’t unusual; the summit of Mount Washington is notorious for terrible weather, and especially for wind. The highest wind speed on Earth – a whopping 231 miles per hour – was recorded here in 1934. I knew when we booked the trip that it was likely that we wouldn’t be able to see much from the top, and for a few minutes, I was right.

But then, Mount Washington’s fickle weather began to work in our favor, and the clouds began to dissipate.

The rest of our time at the summit was beautiful, with mostly blue skies, some fluffy white clouds, and unobstructed views for miles in every direction. Depending on which way we were looking, we could see all the way to Vermont, Quebec, Maine, or Massachusetts. We could even spot the thin line of the Atlantic Ocean along the eastern horizon!

After our hour at the summit, we boarded our return train for the trip back down the mountain. The journey was just as scenic as the way up, though I’m glad I couldn’t see the steep drop in front of us!

By the time we returned to Marshfield Base Station, it was well after noon and we were all pretty famished. There weren’t many open places to eat near the Mount Washington Cog Railway, but that ended up working in E’s favor. The closest place we found was The Grille at the Bretton Woods Golf Clubhouse & Nordic Center near the Omni Mount Washington Resort in Bretton Woods . The resort was incredibly picturesque: a large, white, red-roofed hotel with all the glamor of the turn of the 20th century and a backdrop of soaring mountains.

After a quick drive-by, we parked at the golf course clubhouse and had lunch on the terrace overlooking the 18th hole. E loves golf ( it’s genetic on his father’s side ), so he was in his glory eating grilled cheese and watching the golfers play. Now, when we say we’re going out for lunch, he still often asks if we’re going to eat at the golf course.

After lunch we drove back to our condo. The kids fell asleep almost as soon as the wheels began to move, so M and I got to enjoy the beautiful drive in a reverent silence. Upon our return, M took E to play mini golf at Pirate’s Cove Adventure Golf (I’m serious, the kid’s obsessed) while I did a couple loads of laundry. Later that night, we had a fantastic dinner at Tuckerman Brewing Company , where E’s kid’s meal came with an entire ice cream sandwich that our server decorated with dollops of whipped cream and a generous drizzle of chocolate syrup. 

Best. Day. Ever.

Tips for the Mount Washington Cog Railway with Small Children

• I wrote an entire post about our ride on the Cog , including lots of tips for planning your own trip. Don’t miss it!
• There are no bathrooms on the train, so make sure everyone has a last minute potty break before each leg of the trip.
• Regardless of the weather down below, make sure to bring warm clothes for the summit. 
• Spend some time in the White Mountain National Forest. There were lots of gorgeous-looking hiking trailheads and scenic viewpoints along the way to the Cog Railway.
• Take a hike around the summit of Mount Washington. The Summit Loop trail is fairly difficult but features great views. Make sure to be prepared for any weather.
• In addition to the Cog Railway, train enthusiasts shouldn’t miss the Conway Scenic Railway . These multi-hour journeys depart right from downtown North Conway and travel into the White Mountains. There is also a one-hour Conway Valley Train for small children.

Day 5: North Conway to Jeffersonville, Vermont, via the Kancamagus Highway

The next stop on our family road trip was Jeffersonville, Vermont, where we would be staying in a cabin just north of Smuggler’s Notch State Park  and the legendary town of Stowe. Instead of heading directly to our destination, we decided to take a slightly longer route that included the Kancamagus Scenic Byway .

Especially famous for its fall foliage, the Kancamagus is a 34.5 mile-long section of Route 112 that runs between the towns of Conway and Lincoln. It passes through the White Mountain National Forest and includes plenty of photo stops, hiking trails, waterfalls, picnic areas, and other recreation spots. 

We set off into a cloudy morning, but the views were still beautiful. Again, little hints of autumn colored our way.

Our first stop was the Albany Covered Bridge, about six miles down the highway. We rumbled across the bridge in the car, but then there were lots of small trails and viewpoints to explore the area on foot. It was a peaceful little spot, with the bridge spanning a slow-moving river filled with countless rocks and boulders worn smooth over the centuries.

It was also a great place for E to stretch his legs and indulge in one of his most favorite pastimes (besides golf): throwing rocks into water to see the splash.

There were hiking trails nearby, but we still had a long way to go to reach our destination in Vermont. So we continued west along the Kancamagus.

Within moments, we were stopping again, this time at the Lower Falls scenic area. Located right alongside the highway, it’s impossible to miss. There, the Swift River tumbles over huge boulders and rock formations, creating pretty waterfalls and beautiful pools perfect for swimming.

It was too cold for a dip, so I just spent a few minutes admiring the views before we continued on our way. 

Next on our list was a stop at the Sabbaday Brook Trail, which ambles an easy 0.3 miles to Sabbaday Falls. There are lots of longer or more difficult hikes along the Kancamagus, but this one seemed perfect for our little family.

The Sabbaday Trail and Falls area is a nice place to stop for a snack or meal, as there are a number of picnic tables tucked into shaded alcoves of the forest. My understanding is that it can get crowded in the summer or peak fall foliage season, but we had plenty of space to ourselves when we visited.

E got to spend some more time tossing rocks and sticks into the slow-moving stream, and later we made our way up the trail to the falls themselves. The trail was wide and easy, with a bit of incline as we neared the falls but nothing unmanageable for our two-year-old. It was nice to be surrounded by such lush greenery, with the distant rumble of the falls getting steadily closer.

It didn’t take long at all to reach the falls, which tumbled over a mishmash of rocks in a rush of white water.

A wooden walkway and stairs allowed us to get up close and personal and admire the cataract from all angles.

After giving the waterfall its due, it was time to hit the road again. If we had had older kids or more time, I would have loved to spend the whole day along the Kancamagus Highway. There were so many beautiful overlooks, tempting trails, and other fun places to explore. As it was, however, the troops were getting hungry and tired, so we pushed on.

Especially as we got into some of the higher passes through the mountains, the scenery was just stunning. Eventually, however, we emerged from the national forest and back into civilization. 

It was well into the afternoon by that point, so we stopped at the Woodstock Inn Brewery . There, we enjoyed a tasty lunch on their flower-filled patio until a thunderstorm chased us indoors. 

The rest of the drive into Vermont was quiet, as both S and E fell asleep. We buzzed along the highway before turning off to wind our way through some country roads to our destination. 

We had booked a two-bedroom cabin at Sterling Ridge Resort , a quaint, cozy place in the woods. Our cabin was right on the lake, with a welcoming front porch that looked down a small hill to a fire pit and the lake beyond. 

The inside was nothing fancy, but it was cozy and inviting and had everything we needed for a couple of days in the woods.

That night, M grabbed some food from a local market and we feasted on salad and pre-made stuffed shells at the tiny table in our cabin. I was glad that the cabin was so cozy, because I was disappointed to be leaving New Hampshire so soon. Rather like we experienced after moving on to Ireland from Scotland , we had so fallen in love with New Hampshire that we were worried Vermont wouldn’t compare. Fortunately, we still had a few great days ahead of us.

Tips for the Kancamagus Highway with Small Children

• Lower Falls is a great spot for a picnic or bathroom break, as there are facilities available. Just make sure to keep an eye on the kids and NEVER enter the water if it is high or rushing.
• Make sure to pack water and snacks, as there are no services along the highway.
• Take advantage of the many hiking trails and other scenic viewpoints along the way.
• In warm weather, go for a swim at the Lower Falls.
• The Woodstock Inn also offers accommodations if you’d like to break up the trip to Vermont to really enjoy the Kancamagus.
• Stop at the Old Man of the Mountain Profile Plaza , a beautiful waypoint that overlooks a lake and offers views of the cliffside where the famous Old Man of the Mountain – a New Hampshire treasure – once appeared.

Day 6: Smuggler's Notch State Park

After our long drive the day before, we kept things pretty low-key on our first full day in Vermont. The morning began with E and me taking a walk down to the lake, which was so calm and glassy that its surface reflected the surroundings like a mirror.

Next came a bit of self-catered breakfast, followed by a short drive south into Smuggler’s Notch State Park . The drive took us on a winding adventure through the mountains, with some hairpin turns around giant boulders. Soon enough, we arrived at the trailhead for the Bingham Falls trail . This kid-friendly trail is less than a mile in length and ends at another pretty waterfall: a proven winning combination on the trip thus far.

For the most part, the walking was easy. Our only challenge was getting E to keep putting one foot in front of the other instead of stopping to pick up every stick along the way. The forest was thick and lush, giving the sunlight a greenish hue as it filtered through the trees. 

We found a couple of viewpoints over the West Branch Little River and E again got to toss a few stones before we headed toward the falls.

The last part of the trail descended steeply in a tumble of rocky steps.  Fortunately, the trail was pretty dry so it wasn’t too slippery, but some of those steps were big for E’s little legs! 

We picked our way carefully down and were rewarded with a short waterfall shooting out through the rocks and swirling away down a boulder-filled ravine. 

There were plenty of big boulders to sit on and we had the place all to ourselves, so we set up camp and enjoyed a mid-morning snack. It was so peaceful, quiet except for the sound of rushing water and the breeze rustling the trees. I could have stayed all afternoon.

Eventually, we left Bingham Falls to return to the car. The way down challenged our knees, but the way up challenged our lungs. It was a steep climb, and E was pretty tuckered out by the time we reached the top!

Thankfully, after you summit the rocky steps, the rest of the trail is pretty easy.

In search of a lunch spot, we drove a few minutes further south toward the famous town of Stowe. We ended up at Idletyme Brewing Company , which had another pretty patio where we could soak up the September sun. Afterward, we returned to our cabin to enjoy a lazy afternoon. I couldn’t get enough of these mountain roads.

After being on the go, it was nice to take some time to just enjoy our cabin. We only left to grab a delicious dinner at Martell’s at the Red Fox – one of the few nearby restaurants – and to pick up some s’more-making supplies from the Sterling Ridge main office. When darkness fell, we built a campfire and helped E roast his first marshmallows. It was a perfect night in the mountains!

Tips for Smuggler's Notch with Small Children

• Less steady kids might need a hand descending the stone “stairs” to Bingham Falls. Be cautious after a rainfall, as I’m sure wet rocks would be pretty slippery. Sturdy shoes are a must.
• Do not swim at the falls.
• Route 108, the most direct road between Sterling Ridge Resort and Stowe, closes during the winter.
• It is highly recommended that you make a reservation at Martell’s. 
• The office at Sterling Ridge Resort is well-equipped with anything you might need for your stay, including fun stuff like the s’mores kit we purchased.
• Ride a gondola  from Stowe Mountain Resort to the top of Mount Mansfield, Vermont’s highest peak.
• Winter sports reign in this area, so if you’re visiting in the winter you shouldn’t miss all the skiing, snowboarding, and other outdoor opportunities.
• Sterling Ridge Resort has free kayaks and canoes available to take out on the lake. There are also nature trails, a game room, heated pool (seasonal), and a maple syrup operation in winter!
• Martell’s often features live music , so consider dropping by for a meal or a drink and checking out the local talent.

Day 7: Burlington

For the final day of our family road trip in New England, we headed west to Burlington. A little less than an hour from our cabin, Burlington is a university town located right on Lake Champlain. It has a fun, hip vibe and is the biggest city in the state. We had heard a lot of great things about Burlington and also thought it might provide a nice change of pace from our days in the mountains. 

We arrived mid-morning and parked near the Church Street Marketplace , a pedestrian street lined with shops, restaurants, historic buildings, and other fun attractions. 

After strolling the Marketplace, we turned toward Lake Champlain. 

I had intended for us to take a boat trip out on the lake, but hadn’t been able to find anything kid-friendly that worked for our schedules. It was cloudy and threatening rain, anyway, so we headed instead to ECHO, Leahy Center for Lake Champlain .

ECHO is a fantastic science center that aims to educate families about nature and Lake Champlain. In addition to special temporary exhibits, there are rooms devoted to the care and history of the lake, simple engineering, local marine wildlife, forces of nature, and more. 

Most exciting for little kids like ours is the treehouse area, where toddlers and young children can splash on a water table and engage in lots of imaginative play. There are boats, a market, a cafe, and even a slide!

Most of our late morning and early afternoon were spent at ECHO, with a quick jaunt up to Burlington Bay Market and Cafe for a casual lunch. E had a blast running back and forth to all the kids’ areas and was even enthralled by some of the engineering activities. 

With nap time looming, we said our farewells to ECHO and returned to the car. E had been asking to play putt-putt (mini golf) again ever since he and M played back in New Hampshire, so we found a course near Stowe and set off. The kids fell asleep almost immediately, so M and I took advantage of the quiet to do a little drive through the town of Stowe. It’s a pretty place, obviously a tourist hub, with well-kept buildings and lots of high-end shops and restaurants. 

Eventually, we continued north out of town and made it to the mini golf course. With a putter finally in his hand, E got in his eighteen holes for the day.

Afterward, we grabbed dinner at The Bench , a casual eatery with a wood-fire grill and good beer list. Then it was back to the cabin to enjoy the last night of our New England family road trip. 

Tips for Burlington with Small Children

• The woman who sold us our tickets at ECHO wisely advised us to check out the rest of the science center before visiting the treehouse area, lest the kids get so enamored that they wouldn’t want to leave. She was right!
• ECHO has a comfortable, inconspicuous nursing area just beyond the treehouse toddler space.
• Take a boat ride on Lake Champlain. Make sure to keep an eye out for Champ , the lake’s very own mythical monster.
• Spend some time shopping and enjoying the scenery (and people-watching) at Church Street Marketplace.
• Take a road trip up Route 2 to explore the scenic islands of Lake Champlain.
• Spend the day (or better yet, an overnight ) in charming nearby Stowe.

The next day we left at dawn for our eight-hour-without-stops drive back home. I was nervous for this day; not only would we be dealing with the usual post-vacation blues, but I also wasn’t sure how E and S would do spending so much time in the car. Thankfully, they both did great! 

It took us a long time to find a place to stop for breakfast (the excellent Three Squares Cafe in Vergennes, Vermont), so we got a good 1.25 hours under our belts before giving them their first break. They (and M, in the passenger seat) also took a long nap as we drove through New York, so we were more than halfway home before we had to worry about entertainment. We stopped near Albany to blow off some energy at a playground, grabbed some pre-packaged food from a rest stop service plaza for a quick lunch, and made it home in time for dinner, baths, and bed.

Our family road trip through New England – our first real vacation with kids – exceeded all of our expectations. Sure, there were diaper blowouts and some toddler whining, a couple rain showers and some long drives. But we also got to summit Mount Washington, roast marshmallows over a campfire, hike three different wooded trails, see family, eat great food, and make precious memories spending time together as a family. I’m so grateful that we had this opportunity, so relieved that it went well, and so excited for the next adventure!

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Our First Family Road Trip: 5 Things We Did Right and 4 Lessons We Learned the Hard Way 10 Toddler Road Trip Essentials 15 Road Trip Essentials for Baby

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23 Incredible Road Trips in the U.S.

Whether you’re looking for sweeping views of the pacific ocean or a multiday adventure through national parks, these road trips provide plenty of opportunities to explore the united states..

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Glacier National Park is one of many scenic places you can visit on an American road trip.

Photo by Zack Frank / Shutterstock

In a country as large as the United States, there’s no shortage of destinations and detours to explore by car . Whether your idea of the perfect American road trip entails an epic, cross-country journey or a shorter jaunt through a few of its most iconic national parks , your options are as large and varied as the country itself.

Even if you don’t have the time to drive cross-country, there are plenty of road trip routes (ranging from three days to a week or longer): classic California itineraries , New England routes that shine especially well in the fall, scenic East Coast adventures, and a variety of Midwest journeys for folks farther from the coasts.

No matter your mode of transportation—be it van, RV, motorcycle, or four-door sedan—these are 21 of the best road trips in the nation to consider.

Plan your next Route 66 trip around thirst-quenching stops.

Photo by Peek Creative Collective/Shutterstock

There are many ways to do a cross-country road trip in the USA, but these two itineraries will take you through some truly iconic American places.

1. Chicago to Los Angeles: A Whiskey Road Trip on Route 66

It doesn’t get more American than a 2,000-mile drive along the entirety of Route 66. There are endless ways to take this legendary trip (including an EV version —but to take your cross-country road trip to the next level, we recommend exploring another American pastime: whiskey.

Starting in Chicago and ending in L.A., you’ll stop by some of the leading craft distilleries in the United States, like Few Spirits in Chicago, Still 630 in St. Louis, and Red Fork Distillery in Tulsa. In between tastings, make time for detours to natural attractions, like the Grand Canyon, and quirky roadside curiosities, like Cadillac Ranch in Amarillo, Texas. Just remember to drink responsibly—this is a road trip after all.

Plan your trip

The full itinerary: Put a New Twist on Route 66—Make It an American Whiskey Road Trip

No cars are allowed on Mackinac Island, so you need to park before taking the ferry to this spot.

Photo from Shutterstock

2. Bangor, Maine, to Seattle, Washington: The Great Northern on U.S. Route 2

Covering both the U.S. and Canada, a cross-country trip along U.S. 2 is ideal for anyone who wants to experience the vast diversity and expansiveness of North America. This drive runs the entire top border of the U.S. and showcases otherworldly natural wonders like Acadia National Park in Maine, the Apostle Islands National Lakeshore in Wisconsin, and Mackinac Island in Michigan. The route also passes through Canada, taking road-trippers through Ontario into Quebec—this route may focus on nature, but you won’t want to miss a stop in Montreal or Ottawa.

You’ll also get to explore Montana and Glacier National Park ( reservations may be required ) before passing the Columbia Plateau and ending in the Pacific Northwest’s largest city, Seattle. Don’t miss spending time in the Olympic Peninsula (home to Olympic National Park) for a peek at one of the most scenic places on the West Coast.

3. Dana Point to San Francisco: Driving California’s Pacific Coast Highway

The seemingly endless views of the Pacific Ocean along Highway 1 (also known as the Pacific Coast Highway) are what road trip dreams are made of, and exactly what makes this California road trip so popular. However, with so many stops along the 655-mile stretch, we pulled together a list of the ones well worth pulling over to view. Don’t miss the perfect surfing waves in Santa Cruz, seasonal cuisine in Malibu, an afternoon a the boardwalk in Santa Monica, or a night in Big Sur as you drive between Dana Point (just south of Los Angeles) and San Francisco.

• The full itinerary: The Best Stops for a Road Trip on the Pacific Coast Highway
• The AFAR Guide to San Francisco

The seaside town of Monterey was the setting for John Steinbeck’s Cannery Row .

Photo by Denise Lett/Shutterstock

4. Big Sur to Mono County: A Literary Road Trip Through Northern California

Yes, this itinerary requires you actually put down your book to drive, but seeing some of the pivotal places that shaped American authors will be so worth it. Follow in the footsteps of writers like Jack Kerouac, Maya Angelou, and Amy Tan on this road trip that takes you through literary landmarks in Northern California, such as Caffe Trieste, a meeting place for Jack Kerouac, Allen Ginsberg, Alan Watts, and other bohemian writers and thinkers. This 12-stop itinerary is perfect if you live in the San Francisco Bay Area because you’ll be able to stay make these trips in one or two days.

The full itinerary: The California Road Trip All Book Lovers Should Take

Arizona may take its nickname from the Grand Canyon, but the state has far more natural wonders than just that one.

Courtesy of Shutterstock

5. Phoenix to the Grand Canyon: An Iconic Arizona Road Trip

This 240-mile Arizona road trip takes travelers along some of the state’s most iconic highlights, including its most famous one, the Grand Canyon. A great itinerary for first-time visitors and returning travelers alike, it offers plenty of opportunities for scenic drives, hiking, and biking—as well as tasty food along the way. Hike the 2,704-foot-tall Camelback Mountain in Scottsdale or take in the beautiful red rocks of Sedona on a hike to Cathedral Rock while exploring the Grand Canyon State.

• The full itinerary: The Classic 5-Day Arizona Road Trip
• Grand Canyon guide: The First-Timer’s Guide to the Grand Canyon
• Where to eat in Phoenix: A Chef’s Guide to the Best Restaurants
• Where to stay: The Best Hotels in Arizona ; The Best Airbnbs in Sedona

The Delicate Arch living up to its name in Utah’s Arches National Park

Photo by tusharkoley / Shutterstock

6. Zion to Grand Canyon: A National Parks Road Trip in the Southwest

If you’re looking to visit as many national parks as possible in one road trip, this southwestern itinerary is for you. This journey through Utah and Arizona lets you hike Angel’s Landing in Zion, feel tiny under Delicate Arch in Arches National Park, explore Fairyland Loop Trail in Bryce Canyon, and, of course, raft down the Colorado River in the Grand Canyon. Most visitors to the Grand Canyon remain on the rim, but take at least four days to venture within the canyon and take advantage of the trails and river rafting.

• The full itinerary: The Ideal Road Trip Through U.S. National Parks
• Utah’s 8 Best National Parks and Monuments
• 10 Best National Parks and Monuments in Arizona
• The First-Timer’s Guide to the Grand Canyon

Stop and admire the winding roads of the San Juan Skyway.

Photo by Anh Luu/Shutterstock

7. San Juan Scenic Skyway Road Trip: An Adventure Through Southwestern Colorado

This Colorado trip takes you along the 232-mile loop of the San Juan Scenic Skyway, where you will see plenty of alpine forests, mining towns, and craggy peaks. And for anyone looking to enjoy refreshments after a long day of driving, this route features many opportunities to stop at some of the best breweries in Colorado , such as Ska Brewing Co. in Durango.

• The full itinerary: The Ultimate Southwestern Colorado Road Trip
• Five Classic Colorado Road Trips To Take This Year

In small-town Buena Vista, the riverfront Surf Hotel offers front-row seats to Colorado-style adventure seekers.

Courtesy of the Surf Hotel

8. Denver to Montrose: A 420-Mile Road Trip Through Colorado

Want to explore even more of the Centennial State? Head out on this weeklong road trip where you can fish for salmon in Colorado’s largest reservoir, visit numerous small towns, like Paonia and Crawford, with thriving art scenes along the Colorado Creative Corridor , and explore Black Canyon of the Gunnison National Park, one of the least visited national parks in the nation.

• The full itinerary: Art Stars, High-Altitude Wines, and a Remote National Park: The Ultimate Colorado Road Trip
• Where to stay: The Best Hotels in Colorado
• The AFAR Guide to Denver

Portland may be Oregon’s largest city, but with a population of some 652,000 (or 2.5 million in the larger metropolitan area), it isn’t intimidatingly large.

Photo courtesy of Travel Portland

9. Portland to Astoria: An Oregon Coast Road Trip for Outdoor Lovers

If you love the outdoors, then this six-day road trip along the coast of Oregon is for you. After driving to Coos Bay from Portland, travelers will meander along Oregon’s dramatic, rocky coastline, discovering some quintessentially Pacific Northwest vistas along the way: evergreen forests, seaside dunes, and marine ecosystems. Between stops, there are ample opportunities to stretch your legs hiking, kayaking, or strolling around the region’s small towns—like the historic old town in Florence.

Of course, it wouldn’t be an Oregon road trip without a stop (or three) at a craft brewery, such as Fort George Brewery in Astoria, or cozy coffee shop, like Bread & Roses in Yachats.

• The full itinerary: An Outdoor Lover’s Road Trip on the Oregon Coast
• The AFAR Guide to Portland

The State Capitol Building in Nashville marks the end of this road (trip).

Photo by photo.ua / Shutterstock

10. Seneca Falls, New York, to Nashville, Tennessee: Follow the Path of the Women’s Suffrage Movement

Starting in New York’s Finger Lakes region and ending at the State Capitol Building in Nashville, this road trip traces the route of the national women’s suffrage movement. Highlights include stops at the Susan B. Anthony Museum & House ; Union Square in New York City, which was the site of the first suffrage march; and the Belmont-Paul Women’s Equality National Monument in Washington, D.C.

• The full itinerary: Celebrate Women’s Suffrage on an Epic, Self-Guided Road Trip
• Where to stay: The Best Hotels in Nashville
• The AFAR Guide to Nashville
• The AFAR Guide to Washington, D.C.

Asheville is one must-stop on a North Carolina road trip.

Courtesy of ExploreAsheville.com

11. Charlottesville to Asheville: A Scenic Road Trip Through Virginia and North Carolina

The Blue Ridge Parkway is one of the most scenic drives in the country. Beginning in the soft hilly meadows of the Appalachian Mountains from Shenandoah National Park down into the Blue Ridge Mountains, then into the Great Smoky Mountains, this five-day road trip is best done at a slower pace, which is perfect for admiring the dramatic outlooks and green plateaus. This eclectic itinerary features stops at an art museum, a dairy farm, and plenty of hiking trails.

• The full itinerary: The Ultimate Blue Ridge Parkway Road Trip
• Where to stay: 12 Dreamy Blue Ridge Mountain Cabins You Can Rent on Airbnb and Vrbo
• 8 U.S. National Park Road Trips to Take in Your Lifetime

Dowa:kwe dance group from Zuni Pueblo in 2019

Courtesy of Indian Pueblo Cultural Center

12. Albuquerque to Las Cruces: Discover New Mexico on This Three-Day Road Trip

This route steers you away from New Mexican tourist hot spots like Taos and Santa Fe and instead takes you on a three-day adventure with places that teach you about Pueblo history. You’ll stop at Indian Pueblo Kitchen (formerly known as Pueblo Harvest), a restaurant inside the Indian Pueblo Cultural Center that features Indigenous cuisine ; pick up peppers at Three Brothers in Hatch; and slide down the dunes in White Sands National Park.

• The full itinerary: This New Mexico Road Trip Is the Perfect Introduction to the Land of Enchantment

Historic Fort Martin Scott is one of the places travelers can visit to learn about Fredericksburg’s history.

Photo by Mark König/Unsplash

13. A Five-Day Scenic Road Trip Through Texas Hill Country

This Texas road trip starts and ends in San Antonio with stops in small towns like Bandera, Boerne, and consider a stop in Fredericksburg, which is one of AFAR’s best places to go in 2024 ). Over five days, you’ll find opportunities to stroll in a Japanese tea garden in San Antonio, relax along the Sabinal and Frio Rivers by inner tube, and eat as many tacos as you want. Seriously: You could eat tacos for every meal on this road trip and not get tired of them.

• The full itinerary: Tree Houses, Tubing, and Tacos: The Ultimate Texas Hill Country Road Trip

Mount McKinley looms large on a drive through Denali National Park.

Photo by warnsweet / Shutterstock

14. A Weeklong Road Trip Through Alaska’s Most Majestic Sights

This weeklong drive in Alaska starts and ends in Anchorage. You travel along four scenic byways; explore Wrangell–St. Elias wilderness, the largest U.S. national park; catch sight of Denali, the tallest peak in North America; and enjoy the surprisingly stellar food scene of McCarthy, a one-road town with only a couple dozen residents.

• The full itinerary: Glaciers, Mountain Peaks, and Organic Farms: The Ultimate Alaska Road Trip
• Which Alaska National Parks Should You Visit?

More than geothermal pools, Kirkham Hot Springs features a piping-hot waterfall.

Courtesy of Idaho Tourism

15. Boise to Sun Valley: Explore Idaho’s Scenic Byways

Even a short road trip can be packed with adventure, good food, and scenery, which is exactly what this trip from Boise to Sun Valley along Idaho’s Ponderosa Pine Scenic Byway offers. Although the drive only takes six hours, we recommend taking a few days to explore all the stops and detours along the way. One can’t-miss spot is the Kirkham Hot Springs , where you can stand under a waterfall that will splash you with 135-degree mineral water year-round.

• The full itinerary: The Little-Known Idaho Road Trip You Need to Drive
• Things to do: The Best Outdoorsy Things to Do in Idaho

Grand Portage State Park is the only state park jointly managed by a state and a Native American band.

Photo by Shutterstock/QZ

16. Duluth to Grand Portage State Park: A Scenic Minnesota Sampler

Although there are many appealing road trips throughout the Midwest, this 143-mile, three-hour circuit, which starts and ends in Duluth, Minnesota, is worth keeping in mind. Meandering north on MN-61 with this itinerary, you will enjoy prime views of Lake Superior and towns like Grand Marais, as well as Grand Portage State Park, home to waterfalls, hiking trails, and opportunities to learn about the Ojibwe community who occupy the land today. Once back in Duluth, enjoy a beer at Canal Park Brewing Company before checking into the waterfront Canal Park Lodge nearby.

• The AFAR Guide to Minnesota

Wind your way through colorful foliage in New Hampshire.

Photo by Shutterstock

17. Kancamagus Highway: A Quintessential New England Drive

Yes, you can take a road trip in New England at any time of the year , but this region shows off its best colors in the fall, when locals and tourists alike head out into the country to view the changing colors of the trees. Join other admirers of fall foliage on this popular, 34.5-mile road trip along New Hampshire’s Kancamagus Highway, colloquially known as the “Kanc,” for picturesque ponds, hiking trails, and scenic overlooks.

• Plan Your Fall Getaway With This Peak Foliage Prediction Map

Ogunquit is home to the small, postcard-perfect harbor of Perkins Cove.

Photo courtesy of QualityHD / Shutterstock

18. Maine’s “Lobster Trail”: Travel Route 1 Along the Coast

Traveling Route 1, affectionately known as “the lobster trail,” along Maine’s jagged coastline is an exercise in indulgence. Sample lobster dishes in all forms—buttered, steamed, on a roll, or even in a decadent mac-and-cheese.

The trip starts in the quaint small town of Ogunquit , with its rare (for the area) 3.5 miles of white-sand beach. Make your first lobster of the journey count, steamed with a side of drawn butter at Barnacle Billy’s in picturesque Perkins Cove harbor. Stop at Big Daddy’s for a cone on your way to the shipbuilding center—and summer home of George H. W. Bush—Kennebunkport. Stay at the recently redesigned 150-year-old classic White Barn Inn , and consider a sailing trip for an afternoon. With lobsters cooked in ocean water, the legendary lobster roll at the Clam Shack is a must.

• 8 Scenic East Coast Road Trips to Take This Year

Throughout North Carolina’s Piedmont region, innovative restaurants, shops, and restaurants like Leah & Louise in Charlotte, above, are creating a buzz.

Photo by Peter Taylor Photography

19. Raleigh to Charlotte: A 4-Day Trip Through North Carolina’s Reinvented Core

North Carolina’s Piedmont region extends from the coastal plain to the Blue Ridge Mountains, and includes farmland and rolling wooded hills, especially on the 1-40 stretch near Hillsborough. Starting in Raleigh, drive the short distances to Greensboro, Winston-Salem, and Charlotte to see how these cities are innovating through art, food, and a celebration of the past. Take your time—four days should do—to experience downtown arts districts, James Beard Award–winning restaurants, and civil rights museums that speak truths. Plan your trip

• A Road Trip Through North Carolina’s Reinvented Core

Scenic South Walton is part of the Emerald Coast of Florida.

20. Scenic Highway 30A: A Sunday Drive Through South Walton, Florida

Florida is full of places to cruise with the top down, but it’s hard to beat a Sunday (or any day) drive along Scenic Highway 30A through northwest Florida, home to a postcard-perfect stretch of seaside towns known as South Walton.

The roughly 28-mile route through South Walton County kisses the coast for nearly all its length, taking you through gorgeous residential Gulf-front communities like Rosemary Beach, Grayton Beach, and Blue Mountain Beach . Roll down the windows and let the emerald-hued views in.

Pull over to explore, too—maybe to admire the New Urbanism architecture in Alys Beach or to swim in the clear waters at Grayton Beach State Park . (The beach here has been lauded among the best in the world.)

• The full itinerary: The Florida Road Trip You’ve Been Missing

Stand-up paddleboarding is just one way to enjoy a Florida Keys sunset.

Shutterstock

21. The Florida Keys: An Island-Hopping Getaway

For a sunny road trip itinerary in Florida, skip Miami and head farther south. Beginning in Key Largo and ending in Key West, the Florida Keys Scenic Highway is often overlooked for more well-known routes up north, but it is well worth going out of your way to experience.

As the name suggests, this route is very scenic, so plan to spend at least a few days exploring it and numerous stops along the way. Some highlights include driving across the impressive Overseas Highway, stopping to admire art in the town of Islamorada, and enjoying the historic sites, food, and (of course) beaches in the city of Key West.

• The full itinerary: How to Road Trip in the Lesser-Known Florida Keys

Sun Studio in Memphis was the site of the famous Million Dollar recording session that brought together Elvis Presley, Jerry Lee Lewis, Carl Perkins, and Johnny Cash.

Photo by f11photo on Shutterstock

22. Memphis to Bristol, Tennessee: A Music-Driven Adventure

If you have about a week to spare and a deep appreciation for music, take a road trip from one side of Tennessee to the other, starting in Memphis and ending in Bristol. The eastbound trip spans genres, including rock ( Graceland ), blues ( Beale Street) and, of course, country (did you really go to Tennessee if you didn’t go to Dollywood ?). Nashville serves as the halfway point on your journey—so consider penciling in an extra 48 hours to fully explore the state capital’s greatest hits.

• The full itinerary: 5 Great American Road Trips For Music Fans

The stunning coastline near Cueva del Indio has been the backdrop of star-studded films.

Photo by Alexsf.gr/Shutterstock

23. Arecibo to Condado, Puerto Rico: A Lesser-Known Side of a Well-Loved Island

In the minds of many, trips to Puerto Rico bring images of stunning beaches , delicious foods , and maybe a bioluminescent bay or two . But there’s plenty of history to be found here, too, as Puerto Rico was home to an Indigenous population known as the Taino, a heritage many Puerto Ricans embrace. That history can be explored via a road trip. Starting in the northern town of Arecibo, travel south to Ponce, then back north to Condado—along the way you’ll encounter petroglyphs, Indigenous sites, and breathtaking natural spots.

• The full itinerary: A Puerto Rico Road Trip That Puts Indigenous Culture First

Additional road trip planning resources Picking the route for your road trip is only one part of your planning. From what snacks to pack to which podcasts to listen to, these additional resources will help you prepare for your next adventure:

• Best road trip snacks
• Road trip planning apps
• Podcasts and audiobooks to download
• What to pack for a road trip

This article originally appeared online in August 2020. It was most recently updated on April 4, 2024, to include current information. Additional reporting by Jessie Beck, Erika Owen, Ray Rogers, Terry Ward, and Sheryl Nance-Nash.