family road trip boston to maine

15 Stops on a Boston to Bar Harbor Maine Coast Road Trip Itinerary

Lobsters and lighthouses. Charming towns and rocky coasts. The best way to discover the beauty and uniqueness of Vacationland is with a Boston to Bar Harbor road trip along the Maine Coast. I’ve driven this way many times and each time I discover something new. After so many trips to Maine, I put together this one to two-week Maine coast road trip itinerary from Beantown all the way up to Acadia.

If you are traveling from Boston to Bar Harbor, you will want to take at least a week to explore the Maine coast. Of course, you can drive straight through in under five hours, but there is so much to see on the Maine coast.

This Maine coast road trip includes some of my favorite places to go in Maine in the summer , with stops in:

• The Maine beaches region
• Maine’s midcoast including Boothbay Harbor, Rockland, and Camden
• Acadia National Park

After spending a few days around Bar Harbor, you can then take a fast way back home or continue Downeast off the beaten path to the New Brunswick border.

Where to Stop on Coastal Maine Road Trip

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Day 1-2: Maine Beaches

The first region you will encounter on your Maine coast road trip will be the Maine Beaches. Of course, if you have even more time, you can always add in stops in Salem , Gloucester , Newburyport, or Portsmouth on your way up to Maine.

With a one-week itinerary, plan on spending at least two nights exploring this region. You can always break up two to three nights between two destinations to really get a sense of the differences between the various towns.

Your first stop in Maine is just across the border in Kittery. Kittery is known for its extensive shopping outlets, some of which you may not find in every outlet mall. But I don’t come to Maine to shop, at least not at brand-name outlets.

My first stop is usually at Bob’s Clam Hut , just north of the Kittery outlets on Route 1. While Bob’s is a popular tourist stop, they actually have some of the best lobster rolls and fried clams around. The lines are long for a reason. And yes, the lines are loonnngg. Don’t be surprised to find the parking lot full and the wait for food an hour long in high season.

On my recent trip, I decided to skip Bob’s and try something new so I went where the locals hang out and tried the quieter Chauncey Creek Lobster Pier. You can watch the lobster boats coming in while eating fresh seafood right on Chauncey Creek. But I’ll be honest with you, I still prefer Bob’s.

For a scenic stop, you can also check out Fort McClary, a historic fort in Kittery Point where you can walk along the battlements and get a view of two lighthouses in the distance. There are picnic grounds here for a scenic lunch.

Fort Foster is another great spot for spending a day outdoors, with excellent views of the entrance to Portsmouth Harbor and Whaleback Light, Portsmouth Harbor Light, and Fort Constitution. But you do need to a pay $20 per car parking fee.

Your next stop in the Maine Beaches, about 15 minutes up the coast, should be York Harbor and the York Beaches. Foodies will want to make a pitstop at the Stonewall Kitchen factory store on Route 1 in York. Here you will find all the delicious Stonewall Kitchen sauces, dressings, and other food products, as well as cooking classes and the culinary school, and a cafe.

York Harbor is a quaint oceanfront area with a few rocky beaches that are connected by the York Cliff Walk. If you are looking to stay overnight in this area, the York Harbor Inn is perfectly located right across from the town park and the entrance to the Cliff Walk . The Stage Neck Inn is another great choice.

The York Beaches, both Long Sands and Short Sands Beach are great for surfing, but the accommodations around the beaches are primarily seaside motels. This is also where you will find a majority of the gift shops, restaurants, and souvenir shops. Nearby you have family attractions like York’s Wild Kingdom, mini golf, and more. If you are looking for a quaint downtown and nice sand beaches, head a little further north to Ogunquit.

Cape Neddick

Before you get to Ogunquit, be sure to stop in Cape Neddick, just five minutes further, at the Nubble Lighthouse . Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door (bring cash!) or Dunne’s Ice Cream down the street.

From here, follow Shore Road 15 minutes north into Ogunquit. If you are looking to stay in this area and are ready for a splurge, overnight at the luxurious Cliff House Maine .

Ogunquit is very popular with travelers and many of the hotels and motels are not located right on the beach. So if the beach is your priority and you want to stay overnight, be sure to check and see if your accommodations are truly beachfront. The town itself is quaint and upscale, but also touristy. You will find a mix of fine dining options along with your typical tourist clam shacks and seafood restaurants. Ogunquit makes a nice place for a day trip.

We like to stop into Perkins Cove , the small shopping and dining area on the harbor. I’ve eaten at Barnacle Billy’s in Perkins Cove and it was fine, but there are probably better options in the area. In Perkins Cove, you can take in the view of the incoming fishing boats from the Footbridge, or take a 1.25-mile stroll along Marginal Way, past stately inns and rocky beaches.

Kennebunkport

If you haven’t stopped yet, you will want to bed down for your first night in the popular town of Kennebunkport , just another 25 minutes further north. There are many options near downtown Dock Square, but I would recommend a stay at The Inn at English Meadows . This lovely mid-18000’s Greek Revival-style inn is located in Kennebunk’s Lower Village, just a half-mile walk to downtown Dock Square. Perfect for romantic getaways , this bed and breakfast has been tastefully renovated to offer historic charm with modern luxuries such as Frette fine linens, toiletries by Malin+Goetz, and comfortable Vera Wang beds.

There are some accommodations that can fit a family, but families may prefer a resort such as Nonantum Resort , just south of town and on the water, even if not on the beach.

In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack. We also like to head out of town to Cape Porpoise Chowder House , which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. I’d highly recommend a scenic drive around Cape Arundel, although it will cause some serious house envy!

If you are looking for beach time, Gooch’s Beach is wide and long and great for families, but street parking is limited so get there early. You can also try nearby Goose Rocks Beach or Colony Beach.

Old Orchard Beach

Thirty minutes north of Kennebunkport is another popular beach town. Families love Old Orchard Beach not only because it has a gorgeous, flat, wide beach, but kids also love the rides at Palace Playland and the arcade games at the pier. This section of the Maine beaches feels almost out of place given the rest of the Maine coast, almost as if someone plucked it off the Jersey shore and plopped it in Maine.

My daughter also loves going to Funtown Splashtown , an amusement park/water park, nearby. But if the boardwalk vibe isn’t your jam, you might want to skip over Old Orchard Beach and try Scarborough Beach State Park instead.

Day 3-4: Portland

I would recommend spending one to two nights in the Portland and Casco Bay region, 25 minutes north of Old Orchard Beach. On your way into town, be sure to stop at Portlandhead Light in Cape Elizabeth. It is a great place to scramble on the rocks, walk along the coast, and enjoy those lighthouse views.

We love staying in the Old Port area at the Press Hotel , AC Hotel Portland , Courtyard Marriott, Hilton Garden Inn, or Cambria Old Port. Downtown Portland is a foodie city, with many great restaurants to try. You can also take a tour on the Beer Bus or stop at one of the many breweries nearby. My favorite one to tour and visit is Allagash Brewing Company. For some great lobster with a view, go to Luke’s Lobster on the wharf.

You can hop on a ferry boat and explore some of the islands in Casco Bay, or sign up for a lobster boat tour, where you can learn all about lobstering and help pull up the traps. Best of all, you can eat what you catch! If you don’t want to stay in town, you can also enjoy a car-free couple of nights at the Inn at Diamond Cove on Great Diamond Island.

Read more: weekend in Portland Maine

Freeport (day trip from Portland)

From Portland, you can also take a day trip to Freeport, about 20 minutes north of Portland. Famous for being the headquarters of L.L. Bean , it has become a shopping mecca. In addition to the large company store and L.L. Bean outlet, many other designer outlets and outdoor outfitters have set up shop in town.

You can also stop in for a tasting at Maine Beer Company and sample some of their IPAs. If you are looking for a great lobster roll nearby, head down to the water at Harraseeket Lunch and Lobster Company .

Day 5-6: Maine’s Mid Coast

After your time in Portland, it is time to move on to Maine’s midcoast. This area has miles of coastline, hundreds of islands, and countless charming coves to explore. Picture an open hand pointed down with outstretched fingers and you can imagine the many peninsulas that jut out into Casco Bay and the Atlantic Ocean.

It is good to base yourself in this region for at least two to three nights, broken up between two or more destinations. Although many vacationers might decide to spend a week on Orrs Island and be quite content.

Your mid-coast exploration can start off in the town of Brunswick, a 30-minute drive from Portland, with a walk across the Androscoggin Swinging Bridge . This pedestrian bridge connects Topsham and Brunswick, offering beautiful views of the Androscoggin River. After, take a stroll through downtown Brunswick, home to Bowdoin College.

Harriet Beecher Stowe, the author of Uncle Tom’s Cabin and member of the Underground Railroad, lived and worked in town and her house is now a designated National Historic Landmark. If you need a good lobster roll in this area, head to Cameron’s Lobster House.

From Brunswick, head south on Route 123 to the tip of the peninsula for lunch at Erica’s Seafood . This little hidden gem offers seafood fresh off the boat that you can enjoy at picnic tables overlooking the harbor. From there, turn towards Route 24, which leads down through Sebascodegan Island to the town of Harpswell, Orr’s Island, and Bailey’s Island.

You will get to the end of the line when the road reaches the ocean at Land’s End gift shop. Backtrack a little to the Giant’s Stairs Trail . You can park at the All Saints by-the-Sea Episcopal Chapel and walk along the path that runs parallel to the rocks that make up the Giant’s Stairs. When I went, I was hoping for something more like Giant’s Causeway in Northern Ireland. The rock formations aren’t that unique but it is still a cool view and fun place to explore.

If you have more time in the area, you can spend a day at Reid State Park or Popham Beach, or visit the Maine Maritime Museum in Bath. You may also want to line up for a lobster roll at Red’s Eats in Wiscassett, just don’t make my mistake, be sure to get there before they close! Give yourself about an hour to get from Giant’s Stairs to Boothbay Harbor.

Boothbay Harbor

Boothbay Harbor was one of the first places I visited in Maine, over twenty years ago! I was happy to see that it has only gotten better since my last visit, although the good old Tugboat Inn is still there! This time I stayed at the lovely Harborage Inn , which was located right on the water and just a short walk into the center of town.

In town, there are so many cute shops, from Maine Sea Bags to Sherman’s Books, along with other gift shops, galleries, and boutiques. You will also have your choice of restaurants including Mine Oyster, Kaler’s Lobster, Boathouse Bistro, Ports of Italy, and Shannon’s Unshelled.

For lunch, I would recommend eating fresh seafood outside at Boothbay Lobster Wharf . It is across the bay from town but you can easily walk across the pedestrian bridge connecting the two sides of town.

A very popular thing to do in Boothbay Harbor is to take a whale-watching tour. However, since I’ve been whale watching many times, on this trip I opted for a puffin cruise with Cap’n Fish out to a wildlife preserve on Eastern Egg Rock instead. This 2.5-hour cruise passes by lighthouses on the way, with opportunities to see dolphins or even whales.

The boat is large so it can only get so close to the island, however, the puffins often raft up in the water along the shore so you are bound to see plenty of puffins. Just bring along some good binoculars or a super zoom lens because puffins are small and you won’t get to see their cute, colorful beaks without a little assistance.

Read more: things to do in Boothbay Harbor, Maine

Damariscotta

From Boothbay Harbor, it is only 15 minutes over to Glidden Point Oyster Farm on the Damariscotta River. I was hoping to take a oysters and wine-tasting cruise with Damariscotta River Cruises , but unfortunately, they weren’t running on the day I was in town. So an oyster farm tour seemed like the next best thing!

Eighty percent of Maine’s oysters are farmed in the Damariscotta River! My tour at Glidden Point Oyster Farm explained why the river was the perfect spot for oysters and its history that goes back thousands of years to pre-Colonial times. After learning about the farming process, I stepped up to the window to order some oysters to taste on their outdoor patio. I even learned to shuck an oyster! And I was thrilled to learn that Glidden Point ships nationwide.

If you have more time to stay in the area or prefer a quieter town versus Boothbay Harbor, Damariscotta has a very cute but small downtown. Stop into the Sherman’s Maine Coast Book Shop and Sheepscot River Pottery. You can also visit the Whaleback Shell Midden State Historic Site.

You can stay at the Newcastle Inn and have dinner at King Eider’s Pub or Newcastle Publick House. Locals love Shuck Station Raw Bar and if you want to head a little out of town for some beer tasting, stop into Oxbow Brewing Company at their rural farmhouse brewery.

Pemaquid Point Lighthouse

From Damariscotta, it is a 20-minute drive down to the Pemaquid Point Lighthouse , which can be a great spot for sunset. Of course, when I went it clouded up so I didn’t stick around that long, but that’s ok because I was able to get to my next stop in Rockland a little early.

From Bristol, it is an hour’s drive to Rockland. I took Route 32 through Bremen and it worked out perfectly when I came across a park with fields of beautiful purple and pink lupines stretching down to the water. If you have time, also stop at the Marshall Point Lighthouse (you may have seen this in Forest Gump.)

Rockland is the Art Capital of Maine, a bustling town with art museums, galleries, shops, and restaurants on a working waterfront. It is also a port for Maine Windjammer ships and even small-ship cruises, so it attracts its share of day trippers as well.

It is certainly a larger and more touristy town than many of the others along the Maine coast, but I loved it and returned recently to spend some time before my Maine Windjammer Cruise on the Schooner Heritage.

Make time to visit either the Farnsworth Art Museum , which celebrates Maine’s role in American art, or the Contemporary Arts Museum downtown. If it is open, you can also stop into the Project Puffin Visitor Center to learn about all things puffin. It is a fun town to explore, check out the many murals and public art, and shop at the many boutiques (my favorite was Barefoot in Denim !)

There are so many great spots to eat in town. I had an amazing dinner at Primo, a farm-to-table Italian restaurant just a short drive from downtown. I’d also recommend Rock City Coffee and Rock Harbor Brewing.

If you have time, just south of town follow signs for the breakwater. It is about a mile walk out along the breakwater to the lighthouse at the end, but it is a fun outing on a nice day. Another day trip option is to take a ferry to Vinalhaven, which is known for its beautiful scenery, rocky coast, and granite quarries.

The best place to stay in Rockland is 250 Main Hotel . This modern, art-forward hotel has a rooftop deck overlooking the waterfront and spacious rooms.

Read more: things to do in Rockland , Maine

A 15-minute drive from Rockland, Camden is another popular town on Maine’s midcoast. There are excellent views of the Camden harbor front from the Camden Public Library, and the lawn is a great spot to enjoy a picnic or relax and soak up the view.

Downtown there are many shops and restaurants, such as The Waterfront Restaurant, Peter Otts, and Fresh and Go. If you would rather stay in Camden instead of Rockland, the Lord Camden Inn is right in the center of everything, while the Camden Maine Stay Inn will be a bit quieter and laid back.

Outside of downtown, you can enjoy scenic views from the top of Mt. Battie in Camden Hills State Park. Also, try hiking along Maiden’s Cliff or the Megunticook Ocean Lookout Trail. Unfortunately, during my visit the fog rolled in and I could barely see to drive through that area, let alone take in a scenic view.

Before you get to Bar Harbor on Mount Desert Island, you may also want to stop at the Penobscot Narrows Bridge & Observatory or visit Fort Knox State Park. That was my plan too but with the fog, it wasn’t worth it.

Day 7-8: Bar Harbor

Camden to Bar Harbor is about an hour and forty-minute drive, although you may want to stop in Ellsworth before arriving on Mount Desert Island, for a beer tasting at Fogtown Brewing Company. Instead of staying in the town of Bar Harbor, I chose to stay at Terramor Outdoor Resort about 15 minutes from Acadia National Park and Bar Harbor.

If glamping isn’t your thing, you may want to opt for the luxurious Claremont Hotel in Southwest Harbor or the charming Salt Cottages overlooking Hulls Cove. Of course if you are going all the way to Bar Harbor, you will want to spend some time downtown and walking along the Shore Path along Frenchman’s Bay. From town you can also take a whale watching cruise. Bar Harbor is also a fun town for shopping and restaurants.

If you are visiting Acadia National Park in the summer, be prepared for crowds and make reservations if you want to drive to the top of Cadillac Mountain for sunrise. (You could try this Acadia National Park sunrise hike instead!) To avoid crowds, also check out these things to do near Acadia .

A Maine coast road trip should be on everyone’s bucket list. It is hard to get tired of seeing fishing boats bobbing in a harbor, lighthouses standing tall over rocky coasts, and eating endless amounts of lobster and seafood. Hopefully, this itinerary makes it easier to plan your trip!

Read More Maine Articles

• Best places to go in Maine in the summer
• Things to do in Portland in the winter
• 7 Must-Try Outdoor Adventures in the Maine Highlands
• Maine Highlands Road Trip
• Maine Road Trip Itinerary

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: March 23, 2024

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Boston to Bar Harbor, Maine: Explore the Beauty of A Maine Coastal Road Trip

Have you always dreamed of visiting coastal Maine with your family, and now you want to make it a reality? 

We’re right there with you! Maine is one of the most beautiful places in America, and coastal Maine has long been one of the most popular summer vacation spots on the east coast . It’s filled with towering cliffs, majestic mountains, miles of pristine beaches, and plenty of opportunities to enjoy a good lobster roll. 

The best part is that you can drive from Boston to Bar Harbor in less than five hours (although we recommend taking your time!). 

With the help of our New England expert, we’ve created the ideal Boston to Maine itinerary to help you plan the perfect road trip along Maine’s coast, complete with the best attractions for everyone in your family. So what are you waiting for? Let’s hit the road! 

What is the Distance From Boston to Bar Harbor

How long do i need driving from boston to bar harbor , best time of year to drive from boston to bar harbor, kennebunkport, old orchard beach, boothbay harbor, more tips for road tripping in maine.

The shortest distance from Boston to Bar Harbor is 285 miles. The trip takes roughly four hours and thirty-five minutes direct, with the bulk of the drive being along I-95.  

Coastal Maine is filled with quaint fishing villages and photo opportunities, and our itinerary has you stopping at some of the most beautiful places along the way. 

While you can make a direct drive in a day, we encourage you to make plenty of stops along the way. You won’t regret it! 

Your drive from Boston to Bar Harbor can be as brief or as long as you’d like for it to be. While we suggest that a bulk of your days be spent in Bar Harbor, you can also take a day at each stop to savor all of the unique opportunities each town has to offer. 

You can extend your drive from Boston to Bar Harbor with:

• Stops along the Essex Coastal Scenic Byway in MA
• Add on the American Independence Byway and New Hampshire Scenic Byway, NH

We recommend taking at least 3-5 days to drive to Bar Harbor and then another 2-3 days at your final destination in order to take full advantage of this road trip to Maine. 

The best time to visit coastal Maine is late spring to early summer. However, if you want to avoid large crowds at popular tourist destinations, plan your drive to Maine between May and mid-June or after Labor Day to catch the beautiful New England fall foliage . Otherwise, aim for any time between May and September. 

While locations like Acadia National Park are open year-round, many tourist attractions are only open seasonally, including quite a few of the most popular restaurants and excursions. If you plan on driving from Boston to Bar Harbor in the fall or winter months, we suggest calling ahead to see what’s available. 

Best Stops on a Boston to Bar Harbor Road Trip

It’s time to hit the road; here are the top stops from Boston to Bar Harbor we’d make time for in your itinerary:

Your first stop in Maine is the charming town of Kittery, just over the bridge from Portsmouth, New Hampshire. Founded in 1623, Kittery has no shortage of historical places to visit and natural beauty to explore. We recommend taking at least a day to take in what Kittery has to offer before continuing on with your trip up the Maine coast. 

Take a ferry boat tour of Portsmouth Harbor and the Piscataqua River, where you can take in the sights of Pepperrell Cove, Kittery Point, and Whaleback Light. Or travel on the Memorial Bridge to explore Badger’s Island before visiting Seapoint Beach and Fort McClary. 

If you’re travelling with children, spending an hour or two at the Take Flight Aerial Adventure Park is sure to burn some of that pent-up travel energy! Choose from over 65 activities to climb and even go on a zipline tour! 

Lastly, don’t forget to enjoy some much-deserved retail therapy at Kittery Premium Outlets, featuring several of the best outlet stores in New England. Then grab a bite to eat at one of Kittery’s many fine restaurants, including Robert’s Maine Grill, Chauncey Creek Lobster Pound (a local favorite), or Captain and Patty’s. If you plan on staying the night, the historic York Harbor Inn in nearby York is an excellent option. 

Just a 10-minute drive from Kittery, the town of York is actually made up of four different communities; York Village, York Harbor, York Beach, and Cape Neddick. You can easily take in the sights of “The Yorks” in a day before continuing on your Maine road trip without feeling like you missed out on anything. 

Visiting York Beach is an absolute necessity, if for no other reason than getting a sweet treat at The Goldenrod , a historic candy shop, and cafe that’s been around since 1896. Load up on snacks to take with you to Long Sands Beach, a popular swimming and sunbathing spot. 

If you’re traveling with children, Short Sands beach may just be the place to go. This quarter-mile stretch of sand is surrounded by cliffs, is near a playground in Ellis Park, and also houses Fun-O-Rama, an arcade right there on the sand! 

Pick up some delicious specialty foods and souvenirs from Stonewall Kitchen York Company Store before taking the family to York’s Wild Kingdom , New England’s only zoo AND amusement park. Your kids will love seeing kangaroos, zebras, and even African lions. You can easily spend a few hours of fun, and it’s a perfect stop to add to your Boston to Maine itinerary. 

No Maine coastal road trip would be complete without a stop in Ogunquit, another 10 minutes away from York. You can easily take at least a day to explore all that Ogunquit has to offer, including beaches, museums, performing arts, and more. 

Spend a few hours of pampering at the Cliff House Resort before taking a walk down Marginal Way, a 2.5-mile paved path that provides plenty of photo opportunities and views of the sea. Marginal Way takes you right to Perkins Cove, a picturesque fishing village on the Maine coast full of shops, restaurants, and artisans. 

Go on a whale-watching excursion with Finest Kind or simply relax at Ogunquit Beach. It was voted one of the top 25 beaches to visit in the U.S., and for a good reason. The pristine sand and foaming waves are perfect for strolling, kayaking, or just splashing in the cool water.  

There are also several can’t-miss seasonal activities in Ogunquit, like The Ogunquit Playhouse, a summer theater program. Or you can explore the Ogunquit Museum of American Art, a gorgeous location overlooking the ocean and filled with a richly varied depiction of Maine’s history. 

You must schedule in at least a day of your Maine coastal road trip to enjoy the wonders of Kennebunkport, the summer retreat of the Bush family, and a true Maine treasure. Book a stay in the historic Dock Square area at one of the Captain’s Collection . These stately ship captains’ homes have been converted into luxurious resort-style accommodations for every family. 

Next, explore Dock Square, the hub of Kennebunkport. This area is full of local boutiques and artisan shops, famous restaurants like Striper’s (a Bush family favorite), the Clam Shack, and Old Vines Wine Bar. It’s the perfect place to find one-of-a-kind treasures and souvenirs. 

History buffs will enjoy the impressive sea captains’ mansions along Summer Street and local museums like the one featuring the First Family exhibit at White Columns at 8 Maine Street. The Brick Store Museum and Nott House are also worth exploring, and children will love the Seashore Trolley Museum. 

Whale watching is a popular Kennebunkport tourist attraction, one of many boat tours available along the coast. You can also rent kayaks, canoes, and bikes from several locations in town and choose your own adventure. Snap a pic of Goat Island Lighthouse from Cape Porpoise, fish for stripers on Colony Beach, or take in the breathtaking scenery at Goose Rocks Beach before continuing on your way.

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Drive another half hour and you’ll reach Old Orchard Beach, an essential stop on your Boston to Maine itinerary. Also known as OOB, this scenic spot has been voted Maine’s Best Beach year-over-year, and it’s easy to see why. Your kids will love splashing in the gentle waves, building sandcastles, and enjoying an oceanfront amusement park complete with an old-fashioned carousel. 

The Pier is a popular tourist spot and offers plenty of places to eat delicious food and enjoy cool drinks. Walk 500 feet out into the Atlantic and take in the gorgeous ocean views, live entertainment, and fireworks every Thursday night during the summer. 

There are also several opportunities to explore Old Orchard Beach on the water, whether you’re interested in lobstering tours, fishing excursions, or rafting tours. You can also navigate the Saco River and Scarborough salt marsh by canoe or kayak (if you’re feeling bold!). 

If you have children, visiting Palace Playland is an absolute must. It’s the only oceanfront amusement park in New England, and it’s full of classic rides like a Ferris wheel, roller coasters, and plenty of fun games and tasty fair food. We recommend spending a few hours there before nap time and letting the kiddos sleep on the drive to Cape Elizabeth! 

Not only is Portland the largest city in Maine, but it’s also one of the best Maine coastal towns to visit. There’s something for everyone here, so you’ll want to spend a few days taking advantage of everything that Portland has to offer. From oceanside strolls to five-star restaurants, this unique coastal city has it all. 

You’ll want to spend at least a half-day in Old Port district browsing boutiques and crafts from local artisans. The cobblestone streets and stately architecture are straight out of the early 20th century, but there is also a very modern feel to the architecture.

Experience one of the last remaining working waterfronts in the United States by walking along Commercial Street and tasting freshly caught lobster and fish at several of Portland’s seaside restaurants. 

There are so many fun and exciting things to do in Portland and nearby Cape Elizabeth, like taking a lighthouse tour ferryboat ride or visiting the nearby islands by way of the Casco Bay Ferry Lines. Then, explore Fort Williams Park and see the Portland Headlight, an iconic Maine lighthouse. Just make sure you get a dish of ice-cold gelato at Gorgeous Gelato before moving on. 

Next up on your trip from Boston to Maine is Freeport, a classic Maine tourist destination. You can easily spend at least a day in Freeport, as there are many opportunities to shop, enjoy mouthwatering seafood, and explore this historic coastal town. 

Learn the fascinating history of Freeport by taking a Red Cloak Tour, where you can choose from a selection of different tour options to fit your interests. The Maine Maritime Museum on the Kennebec River is also a treat for family members of all ages, with a range of interesting exhibits, lighthouse cruises, a fishing schooner, and even a kids’ pirate play ship! 

Stop for a sweet treat at Ben & Jerry’s ice cream before doing a little window shopping at Freeport’s many boutiques, antique stores, art galleries, and our favorite, L.L. Bean ’s massive flagship store! Then, break in those new hiking boots by walking Brimstone Hill Trail before sitting down to eat at one of Freeport’s many fabulous restaurants. We recommend Harraseeket Lunch & Lobster Co ., a family-owned Freeport favorite with the freshest lobster rolls in Maine! 

• Stopping overnight in Freeport? Check these family-friendly hotel options

Boothbay Harbor is a welcome stop on your way from Portland to Bar Harbor, and it’s a beautiful place to stop and relax along the Maine coast. This storybook town is a walker’s paradise, with so many shops, trails, and of course, the Boothbay Footbridge, you’ll need at least a day to take in all the sights! 

Boothbay Harbor is famous for its boat excursions and has earned the title of Boating Capital of New England. Take a harbor tour to see nearby Burnt Island and Monhegan Island, and you can even get up close and personal with whales, seals, and puffins! Boothbay Harbor also offers some of the best sea kayaking in Maine, and you can rent kayaks at several shops along the shore. 

There are many kid-friendly activities in Boothbay Harbor, such as the Boothbay Railway Village. There, your children can go on a narrow-gauge railway ride before heading over to the Maine State Aquarium . Kids can touch live lobster and starfish in the aquarium’s petting tank and learn all about Maine’s fascinating marine life. 

Boothbay Harbor is the perfect spot to stop for the night, and there is no shortage of seaside inns and resorts that offer stunning ocean views and all the comforts of home. You’ll also find a wide range of eateries to satisfy even the pickiest of eaters, and you’ll definitely want to top off dinner with some Maine-made ice cream. Kaler’s Restaurant is the area favorite for fresh, affordable seafood, while the Blue Moon Cafe is one of the best breakfast spots in town. 

Last but not least on our Boston to Maine road trip itinerary is Bar Harbor! Otherwise known as the gateway to Acadia National Park , Bar Harbor has been one of America’s most popular summer vacation destinations for over 100 years. As such, there are seemingly endless things to see and do, so we recommend spending at least three to four days at this conclusion of your Maine road trip. 

Summer is the best time of year to visit Bar Harbor, whether you’re whale watching, hiking the trails, or relaxing on the seashore. Book a room at one of the town’s many historic bed and breakfasts, or rent a cottage on Mount Desert Island. There are countless accommodations to suit any preferences or family size, and they’re all equally beautiful. 

Remember the Red Cloak Tours in Freeport? Bar Harbor also offers five unique Red Cloak walking tours for the whole family. Pirate’s Cove Adventure Golf is also a popular pastime, as are the Bar Harbor Ghost Tours .

You can also enjoy cruises, ferryboat rides, lobster fishing, and seal watching (just to name a few). Bar Harbor truly is a treat, and it’s the perfect way to end your adventure up the Maine coast. 

Bar Harbor Accommodation

Be warned, Bar Harbor accommodation fills up fast in the summer months! Try this handy map for finding availability on your dates, with the ability to check availability and prices across different search engines:

• As beautiful as Maine is, you’re still going to encounter plenty of bugs. Mosquitos, blackflies, and moose flies can quickly become annoying, so pack an effective bug spray like Avon Skin So Soft Bug Repellent . 
• Will you be trying lobster for the first time while you’re in Maine? If so, we recommend a seaside restaurant or clam shack along the coast where you can sit outside, roll up your sleeves, and dig right in. 
• You’ll be doing plenty of walking, hiking, and seaside strolling during your Maine road trip, so pack a pair of durable walking shoes and closed-toe hiking sandals. 
• Depending on the time of year, you’re likely to encounter a moose or two while out in nature. While majestic, moose are not particularly friendly, and you want to give them a wide berth. 
• Regardless of how many days you’re taking for your Boston to Maine road trip, we recommend going on a boat tour at one of your stops. Maine’s ocean life is fascinating, and you won’t regret it! 
• Longer to spend in Maine? After you’ve experienced Acadia, head inland and check out these incredible Maine scenic drives .
• Setting out from New York? We have an expanded itinerary to cover every important stop from New York to Bar Harbor, Maine .
• We know how stressful packing can be, and that’s why we created our Ultimate Family Road Trip checklist. It certainly makes packing a much more organized process. 

• NEXT UP: Pack your passports; we’re heading through Upstate New York and visiting Niagara Falls on this incredible Boston to Toronto Road Trip Itinerary .

© Family Road Trip

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Boston to Portland, Maine: The Ultimate Guide to Road Trip Routes and Scenic Stops (2024)

The route from Boston, Massachusetts to Portland, Maine is not a long one- but there are a lot of great places to stop along the way, so it makes a great East Coast road trip. Of course, you can also drive this scenic route in reverse!

Boston is a vibrant city that offers a perfect blend of history, culture, and family-friendly attractions. Families can explore the Freedom Trail, where they’ll encounter iconic sites like the Paul Revere House and the Old North Church as well as world-class museums.

In Portland, Maine, families can immerse themselves in the charming coastal atmosphere. They can visit the Portland Head Light, one of the oldest lighthouses in the country, and explore the Old Port district with its quaint shops and delicious seafood restaurants.

We love road trips- we’ve done a long cross-country route , explored the American Northwest by car, and even driven down into Baja . Although we lived in Boston for many years, we haven’t driven this stretch in a while, so reached out to Laura Mendenhall, a passionate traveler from O Family, Where Art Thou? , to share her experience on this road trip from Boston to Portland, Maine.

Laura spent an incredible three months exploring charming cities along the east coast with her family of 5 in an RV. In this post, they’ll share a bit about their journey from Boston to Portland, Maine including the best routes from Boston to Portland by car, bus, and train, as well as some family-friendly places to stop along the way, and fun things to do while you are there.

This article may contain affiliate links, which means we may earn a small commission if a reader clicks through and makes a purchase.   As an Amazon Associate, we earn from qualifying purchases at no additional cost to you. All our recommendations are our own and are in no way influenced by any advertiser or commercial initiative.

At the bottom of this post,  download a free License Plate Road Trip Game   to play on your next drive!

Lodging: Booking.com Flight Deals: Skyscanner Rental Cars: Discover Cars Airport Transfers: Welcome Pickups

Digital SIM Cards: Airalo eSIM Travel Insurance: SafetyWing

Table of Contents

How far is Boston from Portland, Maine?

Did you know that Boston, Massachusetts is just a short 2-hour drive away from the beautiful city of Portland, Maine? The distance separating these two cities is approximately 109 miles. Whether you opt for a car, bus, or train, embarking on this road trip is truly worthwhile!

Picture yourself cruising along the scenic Interstate 95 North, soaking in the stunning New England landscapes and passing through charming towns. Trust me, the journey is as enjoyable as the destination. So hop in your car, roll down the windows, and let’s embark on this adventure together.

Boston to Portland, Maine: Best Road Trip Routes

You can get from Boston to Portland via car, bus, or even train! Here are the best routes between Boston and Portland, what you’ll see, and even how much they cost.

Are you ready for a road trip? Make sure you have all the road trip supplies , healthy road trip snacks , and car-friendly activities for the kids . Newbie? Not to worry! We’ve got road trip tips for beginners .

Boston to Portland Maine By Car

Direct route: i-95.

The I-95 route from Boston to Portland, Maine is the most direct and popular choice, covering around 110 miles of scenic landscapes. As you travel north, you’ll pass through charming towns, picturesque countryside, and eventually cross the border into Maine.

Make sure to take a break in Portsmouth, New Hampshire, known for its historic appeal. Once in Portland, you’ll discover a lively food scene and a captivating waterfront, making the I-95 route an efficient and enjoyable way to reach your destination.

The Scenic Drive: US-1

If you’re looking for a leisurely and scenic drive from Boston to Portland, Maine, the US-1 route is your perfect choice!

This picturesque coastal road stretches for about 111 miles, taking you through charming seaside towns, breathtaking ocean views, and iconic New England landscapes. Prepare to be captivated by the quaint coastal villages, lighthouses dotting the shoreline, and delicious seafood restaurants along the way.

As you wind your way through this scenic route, you’ll have plenty of opportunities to make memorable stops and explore the beauty of the New England coast. So buckle up, roll down the windows, and get ready for a delightful adventure along the enchanting US-1 from Boston to Portland!

Top Pick: Rent a Car from Discover Cars Discover Cars is our go-to resource for renting cars for road trips. Their pricing is easy to understand, and there are no last-minute surprises. Book Now

Boston to portland maine by bus.

Don’t feel like driving? Taking a bus is another great option and way cheaper than I had expected! To take a bus from Boston to Portland, Maine, you have several options available. Here are some details to help you plan your trip.

Buses traveling from Boston to Portland, Maine typically follow a direct route without scheduled pit stops for town tours. However, there may be brief rest stops along the way for passengers to stretch their legs and use restroom facilities. If you want to explore specific towns, it’s advisable to consider alternative transportation or plan separate trips to those destinations.

How Much Does a Bus from Boston to Portland, Maine Cost?

Approximate ticket prices range from $15 to $35 for a one-way route. The cost of taking a bus from Boston to Portland, Maine varies depending on the bus company, time of travel, and whether you book in advance. It’s recommended to check the respective bus company websites for the most accurate and up-to-date fares, and booking in advance can often secure better prices and availability.

Greyhound offers multiple daily departures from Boston to Portland. Buses typically depart from Boston’s South Station and arrive at Portland’s Transportation Center. The journey takes approximately 2.5 to 3 hours, depending on traffic and specific route variations. Check the Greyhound website for the most up-to-date schedules and ticket prices.

Concord Coach Lines

Concord Coach Lines also operates regular bus services between Boston and Portland. Buses usually depart from Boston’s South Station and arrive at Portland’s Transportation Center. The travel time is similar to Greyhound, around 2.5 to 3 hours. It’s advisable to Visit the Concord Coach Lines website for the latest schedules and ticket information. 

Megabus is another option for traveling from Boston to Portland. They provide daily departures from Boston’s South Station, and the buses arrive at Portland’s Transportation Center. The duration of the trip is comparable to Greyhound and Concord Coach Lines, around 2.5 to 3 hours. Check the Megabus website for the most accurate and up-to-date schedules and fares.

When planning your trip, consider factors such as departure times, ticket prices, and seat availability. It’s generally advisable to book your tickets in advance to secure your preferred departure time and to ensure availability, especially during peak travel periods.

Boston to Portland Maine by Train

Experience the convenience and charm of traveling by train from Boston to Portland, Maine! You will be taking the Amtrak Downeaster and the route would cover approximately 115 miles and offers a comfortable and hassle-free way to explore the beauty of New England.

Amtrak Downeaster Train

The Amtrak Downeaster train provides service between Boston’s North Station and Portland Transportation Center. The ticket prices for this route typically range from $20 to $60 , depending on factors such as the type of ticket and advance booking.

The travel time is approximately 2.5 to 3 hours , offering a comfortable and scenic journey through New England.

It’s advisable to check the Amtrak website for the most accurate and up-to-date schedules and fares and to book your ticket in advance to secure your preferred departure time and ticket type.

Best Road Trip Stop Between Boston and Portland

Whichever route you choose to drive from Boston to Portland, Maine, here are some great scenic stops and coastal towns to see along the way.

Don’t miss our top tips for enjoying a road trip with kids , as well as our best travel tips for kids no matter where you are headed!

The Scenic Route: Boston to Portland via US-1

If you are taking the scenic drive along I-10 from Boston to Portland, here are the must-see scenic stops. These unique and beautiful pit stops along the US-1 route offer a mix of history, natural beauty, and coastal charm, adding a touch of magic to your road trip from Boston to Portland, Maine.

Salem, Massachusetts

Begin your journey with a stop in the historic town of Salem, known for its witch trials. Explore the Salem Witch Museum , stroll through the picturesque streets lined with charming colonial architecture, and immerse yourself in the town’s fascinating history.

Salem is a great place to spend some time- there’s fascinating history here that you won’t find elsewhere in the US. Consider adding a history of Salem walking tour to your road trip itinerary:

Hauntings of Salem Walking Tour

This historical walking tour gets over 5,000 five-star reviews! That’s incredible. Start at the old Town Hall in Salem and learn about 400 years of Salem history from a local historian.

You’ll learn about the Witch Trials Hysteria of 1692, how Salem became a prominent seaport, and stories of some of the families that rose to wealth along the way. You’ll visit the controversial Bewitched Statue of Elizabeth Montgomery, and then end at the Salem Witch Trials Memorial.

“Jeremiah was an amazing guide! He did a wonderful job drawing everyone, of every age, not only into the wicked history of the witch trials, but also shared many other fascinating facts about Salem.” -Katherine p (read more reviews )

This tour is great for all ages, even dogs are welcome! During peak season (October, of course) there may be up to 40 people on this tour. You can choose a daytime tour, or go for a spookier, lantern-led evening tour! Tours run rain or shine. The evening tours book up fast- tours depart as early as 9 am, and as late as 9 pm.

Book Now: Hauntings of Salem Walking Tour

Rockport, Massachusetts

Discover the picturesque coastal village of Rockport, famous for its iconic Motif No. 1 fishing shack and scenic harbor views. Enjoy browsing the art galleries, exploring the quaint shops, and indulging in delicious seafood at one of the waterfront restaurants.

Camden, Maine

Experience the beauty of coastal Maine in the charming town of Camden. Admire the stunning views from the top of Mount Battie, stroll along the scenic harbor, and visit the historic Camden Opera House for a dose of culture.

Windjammer Classic Sunset Sail

Need some time on the water? Pause in this Camden, and take a sunset sail on a classic windjammer. This two-hour boat trip takes you along the Maine coastline, with wonderful sunset views. You’ll sail past Curtis Island Light and into Penobscot Bay. You can help hoist sails, and even take a turn at the wheel of this traditional wooden ship. Departure times vary with sunset.

“The Captain and crew made this the best sail we’ve ever taken! Perfect 2 hour family sail and the Captain told the entire history of the ship and why these are so important to our history.” -Amy_V (read more reviews )

Book Now: Windjammer Classic Sunset Sail

Pemaquid Point, Maine

Make a stop at Pemaquid Point to see its iconic lighthouse perched on rugged cliffs overlooking the Atlantic Ocean. Explore the surrounding rocky shores, visit the Fisherman’s Museum, and capture breathtaking photos of the dramatic coastal scenery.

Boothbay Harbor, Maine

Immerse yourself in the quintessential coastal charm of Boothbay Harbor. Take a scenic boat tour to explore the nearby islands, visit the beautiful Coastal Maine Botanical Gardens, and savor fresh seafood at one of the waterfront restaurants.

The Direct Route: Boston to Portland via I-10

If you are taking the direct route (I-10), from Boston to Portland, here are the must-see pit stops. These pit stops offer a mix of natural beauty, cultural attractions, and coastal charm, making your road trip from Boston to Portland, Maine, even more memorable.

Portsmouth, New Hampshire:

Explore the charming waterfront city with its historic architecture, bustling marketplaces, and picturesque coastal views. Don’t miss a visit to Strawbery Banke Museum , where you can step back in time and experience life in early America.

This is a great place to stop and do an Islands and Harbor Portsmouth Bike Tour !

Kids 10 and up can participate in this tour. During this 2-hour bike tour , you’ll ride across the Piscataqua River and head to the outer islands of Portsmouth, learning stories about the area as you go, including about “Live Free or Die” Captain John Stark.

“A fun adventure filled with history, moderate exercise, and lovely views. We had time to enjoy a break at each stop while we learned about each location.” -victoria (read more reviews )

Book Now: Bike Tour of Portsmouth Harbor and Islands

Kennebunkport, Maine

Discover the coastal beauty of this quaint town known for its stunning beaches, charming shops, and delightful seafood. Visit the iconic Cape Porpoise Pier, take a scenic boat tour, or indulge in a delicious lobster roll.

Family Detour: You can do a fun scavenger hunt in Kennebunkport- this hunt takes about two hours, and will have you exploring the town both inside and outside. You’ll have challenges, solve clues, and interact with a live (but remote) host. Players give it five stars!

Book Now: Family Scavenger Hunt in Kennebunkport

Ogunquit, Maine

Experience the natural beauty of Ogunquit with its pristine sandy beaches, rugged cliffs, and scenic coastal walks. Take a stroll along the Marginal Way, a picturesque footpath that offers breathtaking views of the ocean.

Portland Head Light, Cape Elizabeth

Make a stop at this historic lighthouse, one of the most photographed in the United States. Enjoy panoramic views of the rugged coastline and capture memorable photos of the iconic red-and-white striped tower.

Freeport, Maine

Shopaholics will love a visit to Freeport, home to the famous L.L.Bean flagship store and numerous outlet shops. Explore the charming downtown area, dine at delicious seafood restaurants, and enjoy the vibrant atmosphere.

Best Stops from Boston to Portland via the Train

These fun and interesting pit stops along the train route from Boston to Portland offer a diverse range of experiences, from beachside fun to cultural attractions and scenic beauty, ensuring an exciting and memorable journey.

Old Orchard Beach, Maine

Get off at the Old Orchard Beach station and spend some time exploring this vibrant beach town. Enjoy the sandy shoreline, take a stroll on the iconic pier, and indulge in classic seaside treats like ice cream and fried dough.

Hop off at the Freeport station and discover the famous L.L.Bean flagship store , where you can shop for outdoor gear and clothing. Explore the charming downtown area, browse through unique shops and boutiques, and sample local cuisine at one of the cozy restaurants.

Brunswick, Maine

Take a break at Brunswick and visit Bowdoin College , a prestigious liberal arts college known for its beautiful campus and cultural offerings. Explore the college grounds, visit the Bowdoin College Museum of Art , and take a leisurely walk through the quaint downtown area.

Portland Head Light, Maine

Arrive in Portland and make your way to the iconic Portland Head Light, one of the oldest lighthouses in the United States. Enjoy stunning views of the rugged coastline, learn about the history of the lighthouse, and capture memorable photos of the picturesque surroundings.

Old Port, Portland, Maine

Step off the train and venture into the charming Old Port district of Portland. Explore the cobblestone streets lined with boutique shops, art galleries, and waterfront restaurants. Take a scenic harbor cruise, sample fresh seafood, and soak in the lively atmosphere of this historic old port area.

Visiting Boston: Top Things to Do with Kids

There are so many things to do in Boston for all ages, here are just a few of the things that we enjoyed in our time there, that we highly recommend for families. These unique attractions in Boston offer memorable experiences that are sure to captivate the imaginations of children.

Whether it’s participating in a historical reenactment, learning about the American Revolution, exploring the city by land and water, or encountering fascinating wildlife, there’s something for every young adventurer in Boston.

Boston CityPASS

If you’ll be spending a few days in Boston, consider getting a CityPass – it’s good for 9 consecutive days from when you first use it. It includes admission to the New England Aquarium (one of our favorite places in Boston!) and the Museum of Science, Boston (also amazing), plus two other attractions of your choice, including a Boston Harbor Cruise.

Book Now: Boston CityPASS

Boston Tea Party Ships & Museum

Step back in time and relive the iconic Boston Tea Party at the Boston Tea Party Ships & Museum . Kids can participate in a reenactment, throw “tea” into the harbor, and explore interactive exhibits to learn about this pivotal event in American history.

Freedom Trail

Discover the thrill of exploring the renowned Freedom Trail with your family. This 2.5-mile historic route showcases 16 significant sites which immerse your children in American history. The trail starts at Boston Commons, the oldest public park in the country, and includes Paul Revere’s House, and the USS Constitution Museum among others.

You’ll get the most out of the Freedom Trail with this five-star small group tour . No more dragging your kids over to read placards! This tour starts at Boston Commons, lasts 2 1/2 hours, and ends at Copps Hill.

“Ted was an amazing tour guide and historian. He brought the story to life and told it how it really happened not what we want to believe happened.” William_S (read more reviews )

Book Now: Small Group Freedom Trail Walking Tour

Boston Duck Tours

Hop aboard a colorful renovated World War II amphibious vehicle and embark on a Boston Duck Tour , a unique way to see the city. Kids will love the exciting ride that takes them through the streets of Boston and then into the water for a scenic cruise along the Charles River. The big “splash” into the water is always a favorite moment!

Duck tours last 1 1/2 hours, and cover most of the major sites in downtown Boston from Boston Commons to Newbury Street, to the Prudential Center. This is a great way to get an overview of the city if it’s your first time visiting Boston.

“t was really cool hearing the back story to a lot of historic buildings, and it’s a great way to start your trip to Boston off. It gave a lot of places and ideas for what to visit in person next! “ Tia_E (read more reviews )

Book Now: Boston Duck Tours

Other things we highly recommend doing in Boston: a tour of Fenway Park , and a walking food tour of the North End (Italian quarter).

Visiting Portland Maine: Top Things to Do with Kids

Portland Maine has a ton of family-friendly activities, here are some of our favorites that we highly recommend to other traveling families. These fun and easy activities in Portland, Maine, provide opportunities for family bonding and exploration.

Whether it’s marveling at a historic lighthouse, engaging in hands-on learning at a children’s museum, or enjoying a scenic ferry ride, Portland and the old port area offers plenty of family-friendly attractions for all to enjoy.

Explore the Portland Head Light

Visit the iconic Portland Head Light, a historic lighthouse perched on the stunning shores of Cape Elizabeth. Take a leisurely stroll along the scenic trails, enjoy a picnic with a view, and let the kids explore the rocky beach for seashells and tide pools.

Portland City and 3 Lighthouse Historical Tour

If you really want to see iconic lighthouses, take this 1.75-hour lighthouse tour that includes the city of Portland, as well as visits to three lighthouses: Portland Head Light, Spring Point Ledge Lighthouse, and Portland Breakwater Lighthouse. You’ll be led by a librarian who knows the city well and will share local lore along the way.

Book Now: Portland City and 3 Lighthouse Historical Tour

Take a Casco Bay Ferry Cruise

Embark on a family-friendly cruise around Casco Bay, where you can enjoy picturesque views of the coast, islands, and lighthouses. Choose from various cruise options, including narrated tours or island-hopping adventures, and make lasting memories as you sail together on the sparkling waters.

Casco Bay Tall Ship Cruise

This windjammer cruise is two hours of cruising on the ocean. Help hoist the sails on this traditional wooden boat, then sit back and watch for wildlife along the shores.

“What an experience and what a gorgeous boat! The cruise led us around the harbor that’s steeped in history. The captain and his crew invited us to participate in raising the sails, how fun, and we saw two seals while cruising, so cute!” -Heather_B (read more reviews )

Book Now: Casco Bay Tall Ship Cruise

The Casco Bay Narrow Gauge

The Main Narrow Gauge is a charming, historic railway that offers scenic rides along the waterfront of Portland, Maine. With its vintage steam and diesel locomotives, the railroad provides a unique experience for families to step back in time and enjoy the picturesque beauty of Casco Bay.

Other things we recommend doing in Portland: Take a one-hour open-air trolley tour of the city, or take a donut-tasting walking tour !

FAQs: Boston to Portland, Maine Road Trip

Boston and Portland, Maine are approximately 109 miles apart, making it a convenient and relatively short distance for a road trip or other modes of transportation between the two cities. The short distance means you have a lot of time to stop and explore the area in between these cities. Keep in mind, once you are in Portland, you are only three hours from the epic Acadia National Park .

The best time for a road trip from Portland, Maine to Boston is during the summer months of June to August, with favorable weather and abundant activities and events to enjoy along the way.

Unfortunately, no, there is not a direct ferry that goes from Boston to Portland, Maine. However, there is The Casco Bay Lines which operates a ferry service between Portland, Maine, and the Casco Bay Islands. 

Yes, you can take a bus from Boston to Portland, Maine. Several bus companies, such as Concord Coach Lines and Greyhound, offer regular bus services between the two cities, providing a convenient and affordable transportation option for travelers.

The halfway point between Boston, Massachusetts, and Portland, Maine is typically around the Wells area. It’s approximately 55-60 miles from both cities and serves as a convenient rest stop for travelers on the route. Wells is known for its beautiful beaches, charming downtown area, and various dining options, making it a great place to take a break during your journey.

There You Have It: Boston to Portland, Maine Road Trip Routes

A road trip from Boston to Portland, Maine is an ideal family vacation, offering a blend of natural beauty, historical sites, and family-friendly attractions. There are countless benefits of traveling as a family . My family and I made lasting memories and look forward to taking this road trip again!

With this road trip itinerary, you can explore picturesque coastal towns, visit charming lighthouses, and indulge in fresh seafood. Kids will love the sandy beaches, scenic hiking trails, and the chance to learn about American history at museums and landmarks.

This travel guide allows for flexibility and discovery, allowing families to create memorable experiences together. From stunning landscapes to engaging activities, a road trip from Boston to Portland offers something for everyone, making it a perfect choice for a summer family getaway.

Traveling along the East Coast? We’ve got lots of family road trip stops , including guides to visiting Washington DC , and a beginner’s guide to New York City .

Cynthia Matthews von Berg is the founder of Sharing the Wander. She is a passionate traveler, mom, and travel coach specializing in long-term travel and family travel. She and her family embarked on a Family Gap Year in 2021, and haven't looked back.

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Boston Road Trip – Epic Maine Coastal Drive To Acadia National Park

By: Author Sunset Travellers

Posted on Last updated: July 22, 2019

Categories Road Trips , Travel , United States

Welcome to our ultimate 8 day Boston road trip guide on the Maine Coast including Acadia National Park.

We’ve recently completed an 8-day Boston road trip up to Acadia National Park.

We had an absolutely incredible time and wanted to share as many tips about this road trip as we could! 

There is so much to see on the way that you probably would need a month or two to explore every bit of the coast, therefore planning this trip was not easy.

We tend to do very little research when travelling to a new destination and ask locals once we get there.

However, this Boston road trip felt different and we felt like we should plan our trip ahead of time.

So let’s get into the details and tips for our incredible Boston road trip!

Our overall experiences during the road trip.

• We travelled from the 17th to the 25th of June and got all different weather conditions.
• From 30 degrees celsius and no cloud in the sky to 12 degrees and pouring rain all day long.
• The coastal weather, although bit unpredictable, allowed us to discover different sights and gain different perspectives on the area.

If you are planning to travel this time of the year, make sure to pack a rain jacket and extra layers of clothing.

Here are a few things you should know before travelling from Boston to Acadia National Park.

Weather and best time to travel the coast of maine to acadia national park.

• The best time to visit Acadia National Park is by far outside of the high season (July and August).
• March, April and May can be very wet.
• June, September and October are the best times to travel the coast of Maine, as you can enjoy your sightseeing with warm weather and fewer crowds.
• When travelling the coast of Maine, keep in mind there is plenty of mosquitos and black flies.

We were fortunate as there were no black flies during our trip, but make sure to have a mosquito/bug repellant at all times with you.

The second you stop on a hike, bugs can quickly become unbearable.

You might also want to consider purchasing bug sprays ahead of time. We visited three shops before grabbing the last two repellants on the shelf.

What to wear on Boston road trip

If you are planning to travel the coast of Maine this time of the year, make sure to pack comfortable, light clothing, one or two jumpers and a rain jacket.

• Quality shoes or hiking boots are also a must if you want to explore the area.
• Always travel with some extra water, suncream, sunnies, hat and a good map.
• We found workout clothes to be the best suited for the trip, you might, however, want to consider some long pants and long-sleeved tops.

Car rental and fuel costs on coastal Maine road trip

We booked our car rental through Thrifty.

• Total cost for an SUV came to USD 1200, including comprehensive insurance.

The fuel bill came to USD 115 for the entire trip, it was an eco SUV apparently. 

We took the coastal route at all times; therefore we also avoided tolls which can quickly add up to a hefty bill.

You can opt-in for a toll package with your car rental provider but it worked out as USD15 extra per day so decided against it. 

Although we made sure to select “avoid tolls” on Google maps, we were still billed USD 71 for tolls. 

We also stocked up on some of our best travel snacks for the road to avoid unnecessary stops. 

We also had some awesome tunes to play from our road trip playlist. 

Where to stay on Boston road trip

We stayed in Inn’s, Airbnb’s and B&B’s averaging USD 120-150 per night.

We will include more details on the accommodation as we go along our Boston road trip route.

Airbnb is by far our favourite way to book a place to stay.

You actually get to stay in local areas, away from busy hotels and explore the surroundings like a local.

If you are new to Airbnb , make sure to read our guide to booking your first Airbnb and get a $76 discount towards your first stay .

Now onto our Boston, coastal Maine and Acadia National Park road trip itinerary!

Boston to newburyport road trip – 1-night stay in newburyport.

Newburyport is a small charming coastal town, located on the waterfront.

It takes approximately 45 minutes to get to Newburyport from Boston Airport.

As we had a late flight, we only arrived in Newburyport at 7 pm. We booked our first accommodation via Airbnb at Market Street Inn .

The place is very well located within short walking distance to the town centre and the waterfront.

The first night we had a seafood dinner at Michael’s Harborside restaurant .

The lobster haddock and Michael’s seafood pasta toss were delicious.

We didn’t realise how big the portions are going to be so probably could have avoided eating bread before the food arrived.

The next day we went to explore Plum Island and the Park River National Wildlife Refugee .

Make sure to add this stop in as Plum island is an incredible site. It is only about 10 minutes drive from the centre of Newbury port 

The Plum island took its name from the beach plums that grow wild along the dunes.

The area is very calm and perfect for enjoying a walk, cycle or run.

To visit the Wildlife Refuge, you will need to pay USD 5 entry fee (valid for 24 hours) per car. 

• It takes about 30 minutes to drive from the entrance to the end at Sandy Point .

Here you can enjoy peaceful nature at its best, with several walking trails and bird-watching platforms, you can easily spend a few hours here taking in the scenery.

After you are done exploring, head for breakfast at the Tennery Historic Marketplace .

• Here you will find several quality restaurants and many unique craft shops.

We took our time here and did a bit of shopping.

If you wish to grab a bite to eat before you hit the road again, we highly recommend Black Cow Tap & Grill .

We got to enjoy an evening meal on the way back to Boston the last day, and their food was fantastic.

Newburyport to Portland road trip

The drive from Newburyport to Portland is spectacular!

Take the 1A route that will take you along the coast through the beach town of Hampton and continue to 1B through New Castle and Portsmouth.

Portsmouth has several restaurants to choose from if you get hungry.

We were looking forward to Surf Portsmouth restaurant. Unfortunately , they were closed when we got there (they are only open from 4 pm on that Tuesday).

We opted in for the River House restaurant instead. Although the portions were generous, they lacked a lot of flavours, and they don’t have any healthier options available on the menu.

When here, however, keep an eye on the Memorial Bridge .

The World War I Memorial Bridge is a vertical-lift bridge that carries U.S. Route 1 across the Piscataqua River between Portsmouth, New Hampshire, and Badger’s Island in Kittery, Maine, United States.

It is an impressive sight to see when they lift the bridge for massive cargo ships to pass.

When you are ready to hit the road again, continue on Route 1 and go over the Memorial Bridge, then turn right onto 103 towards Kittery.

Pass the Cuts Island where you can stop and stretch your legs.

The Cutts Island loop trail is less than 3km long perfect for all skill levels.

If you decide to skip the trail, continue on 1A to Cape Neddick and the Nubble Lighthouse .

From here we decided to go back on the road and head towards Portland as it was already 4 pm and we still had a good 1-2 hours of driving ahead of us.

If you, however, want to stretch your journey and explore some attractions along the way, here are few places you should check out.

• Rachel Carlson National Wildlife Refuge – established in 1966 in cooperation with the State of Maine to protect valuable salt marshes and estuaries for migratory birds.
• Kennebunkport – This small coastal town, beloved by sea captains who once built their mansions here, has a lot to offer. From exploring the city, kayaking, sailing, whale watching or fishing to enjoying some of the summer events held here. You can easily add this town to your itinerary without regret.
• Old Orchard Beach – The famous Old Orchard Beach Pier, located right in the centre of the beach the pier was first built in 1898 and once marched over half of km out into the bay. The 11 km beach attracts all ages during the summer offering a range of activities to suit all.
• Scarborough Beach State Park – Open from 9 am to 8 pm during the season, the state park can be visited for a fee. Scarborough Beach offers some of the best swimming in the area during the summer months. Take your swimming gear and enjoy the day at the beach.

Portland to Camden road trip – 2 nights in Portland

Welcome to the part of your road trip where Lobster rolls become a way of life. 

Steve ordering Wasabi flavoured lobster rolls! INCREDIBLE!

When you get to Portland, you quickly realise that the town is much bigger than what you saw on your way here.

We booked an Airbnb for the two nights located about 20 minutes walk outside the historic downtown.

Although the place was beautiful, it lacked a lot; therefore we decided not to include it in our post.

Instead, we recommend booking something centrally located if you want to explore downtown.

Here are some of the best places to eat in Portland, Maine

As you can imagine, the area has plenty of restaurants to choose from, and we could not miss some of the best seafood in town.

• Eventide Oyster Co – This place is a must if you are after fresh seafood and oysters. We went for dinner here the first evening, and the place was packed. Expect to wait 20-40 minutes for a table if you haven’t booked in advance.
• Fore Street Restaurant – Your farm to table experience. The food is delicious and a must-visit when in Portland. Keep in mind to book your table well in advance.
• Central Provisions – This restaurant specialises in small plates, craft cocktails and craft beer and wine. We had to give it a try, and the place did not disappoint
• Blyth & Burrows – Our favourite place to relax after a day of sightseeing. Serving great cocktails and delicious food. The cheeseboard is a must-try!
• The Portland Hunt & Alpine Club – This place was recommended to us by one of the locals. Although we went there only for a cocktail, the food looked fantastic.
• The Holy Donut – You can’t say you’ve been to Portland without trying the doughnut! They melt in your mouth. Our favourite? Must be the Maine blueberry.

Things to do in Portland Maine

A lobster roll with a view!

There is a countless amount of places to see here.

Our main goal was to explore some of the areas famous lighthouses and of course, try a few lobster rolls.

We achieved the second goal more often than the first one due to the weather. In fact, some days Steve suggested that maybe he would turn into a lobster soon haha.

When we have first researched the area, we were surprised by the amount of grey looking photos, now we see why.

We had non stop rain for two days straight! But as it is on the Atlantic coast their tend to be more overcast days than clear days.

Hopefully, on your Boston road trip, you will be luckier than us! Let us know in the comments if you were. 

The first day, after we woke up in our Airbnb, we were forced to change our plans and stay indoors, the next day before we left for Camden, we managed to see one of the most famous lighthouses, the Portland Head Lighthouse .

The Fort William Park, where the lighthouse stands, offers several walking trails with views over the rugged coastline.

Portland restaurants famous for its lobster rolls always compete over who’s lobster roll is the best.

We got to try several of them and found two best lobster rolls in Portland:

• The Lobster Shack At Two Lights – super fresh and soft lobster
• Bite Into Maine – this place has two locations, one by the Portland Head Lighthouse and the second one in Scarborough. We tried both and seriously the wasabi lobster roll is hands down the best lobster roll we ever had.

Here are a few must-visit places in Portland we planned to see , but due to the weather, the plans have changed. 

• Eastern Promenade and the East End Beach
• Bug Light Park
• Go on a cruise and catch some lobster with Lucky Catch Cruise
• Visit the Two Lights State Park
• Relax at Crescent Beach State Park
• Take a brewery tour
• Explore nearby islands

Portland to Camden road trip – 2 nights in Lincolnville

Halfway up the Mt. Betti hike early morning. Highly recommended!

After Portland, we headed straight to Camden on route 1 for our two-night stay at Victorian By The Sea Bed & Breakfast .

We stopped quite a lot on the way even though it was only just under two-hour drive, and it took us over 3 hours to get to our accommodation.

If you get hungry, make sure to add a stop at the Red’s Eats and grab their famous lobster roll.

This route will take you through many charming towns and countless opportunities to wander off and explore the surroundings.

Just on the way to Camden, you will find Portland with a famous fine dining Italian restaurant, the Promo Restaurant .

Camden and nearby towns offer a variety of dining options.

Some of the restaurants near Camden and Belfast we enjoyed :

• Whale’s Tooth Pub & Restaurant
• Young’s Lobster Pound

There is a countless amount of restaurant options here, so choose wisely as many places may not deliver the quality you are looking for.

Things to do in Camden Maine area:

• Cellardoor Winery – If you are a wine enthusiast like we, you can’t miss the Cellardoor Winery in Lincolnville.

The winery offers fantastic views over the region, while you get to taste some quality regional wine.

It’s hard to believe that grapes can survive Maine’s climate.

Aurora was our favourite wine we got to taste here.

The Cellardoor Winery is a perfect place for an afternoon picnic with friends and family or a romantic day away for two.

• Back and Forth ferry – The Back and Forth is a traditional wooden lobster boat offering a short and delightful trip around the bay.

You get to see Belfast from the water and learn more about the history of the area as well as lobster fishing.

• Camden Hills State Park – The park offers some of the best views of the area, and you can purchase a daily pass to the park at USD 6 per person.

Although most viewpoints are easy to get to via car, you can also choose to hike.

We decided to hike to Mt. Bettie early morning and got rewarded with stunning views of Camden and nearby islands.

• Rockport and Rockport Harbour – Here you can easily spend a few hours exploring the area.

It is a perfect place to stay active and explore the area by foot or bike. The Beauchamp Point offers panoramic views of the area.

• St. George Peninsula – If you have more time, head to St. George and explore museums, taste Maine wine at the Breakwater Vineyards or hop on a cruise in a search for puffins.

Camden to Acadia National Park road trip – 2 nights at The Birches Acadian Bed & Breakfast 

From Camden, we continued on Route 1 to Southwest Harbour where we’ve booked our accommodation.

It takes about 1 hour 30 min to reach the National Park, and you immediately notice how the landscape changes and how much greener it gets.

The closer you get to Acadia National Park, the more you feel like you are emerging in nature.

We got the best three days weatherwise and managed to do a lot of hiking, even in such a short time.

The good news about the park is that the peaks are not as high, and you can easily do 2 to 3 hikes in one day.

The first day we recommend exploring the area by car and doing small hikes to get to know the place.

Everything is within a short drive. Therefore, you can easily get to some fantastic viewpoints within minutes.

On day one in Acadia National Park, we did the following:

Wonderland trail – nice easy walk with a rewarding view at the end of the trail.

Bass Harbor Lighthouse – effortless walk down the steps; you will have to go over the rocks to get a good view of the lighthouse. Lovely place to chill for a while and enjoy the views.

Ship Harbor Trail – another very easy trail that offers some fantastic views along the way.

Bar Harbor – This town has everything, from an endless amount of bars, restaurants, shops and more. It is a great place to walk around but might be too busy if you are looking for a relaxing and quiet break.

Day two – best things to do in Acadia National Park:

The lovely Bass Harbor Lighthouse

The second day we did two different hikes, with a lunch break at Beal’s Lobster Pier.

The first hike to the Mansell Mnt . took us about two hours up and down.

It does get a bit tricky in one or two parts going down, but overall, it was a fantastic hike with fantastic views.

The best part was that there were not too many people, so we got to enjoy nature.

The second hike we started at the Brown Mount Gatehouse carpark.

We took the carriage road passing the stone bridges and headed up to Bald Peak .

The second you get to the top, 360-degree views reward you. We couldn’t get enough how the coast does not end.

Day three – best things to do in Acadia National Park :

Before we headed on the road back to Boston, we went up to the Cadillac Mountain .

At 466 meters, the mountain is the highest peak in the park and can be easily accessible via car.

We strongly recommend getting here very early at sunrise or late at sunset to enjoy nature at its best.

It gets jam-packed up here, and you can be stuck waiting for a car space for a long time during the season months, therefore plan ahead of time.

Best places to eat in Acadia National Park:

Our personal best three places we went to are the following.

Seafood Ketch – a quality restaurant with a great view, serving delicious seafood. Best lobster we ever had!

Beal’s Lobster Pier – The food is prepared fresh on the spot.

Charlotte’s Legendary Lobster Pound – Fantastic lobster rolls.

Final notes on our Boston road trip to Acadia National Park

No matter how many days you have, Acadia National Park is a must-visit.

Although our eight days felt a bit short, and we would love to add a week to our itinerary, we are thrilled to explore this part of the world.

Sure we only scratched the surface as there is so much more to see, but that is not the point, the most important thing is to enjoy every second of your trip.

We strongly recommend planning your days ahead of time to get the most out of your trip.

Please comment below with any questions or tips you might have for Boston road trip. 

If you enjoyed this post be sure to check out some of our other road trips here.

Thanks for reading be sure to share! 🙂

Thanks for stopping by,

Sabina and Steve

Boston to Maine: 5-Day New England Fall Road Trip Itinerary

This post contains affiliate links which means that I will make a small commission if you purchase a product after clicking on any of them, at no extra cost to you.

Fall is my absolute favorite time of the year! We don’t get to experience much of the lovely fall weather in Tampa , so it always feels like the perfect time to make a trip up north. New England is one of the best (and most popular) places to road trip in the fall!

There are so many activities available during this season! Go leaf peeping in New England or do an apple cider tour in Vermont. This fall road trip will take you from Boston to Portland Maine, making stops along the way that showcase some of these unique cities and towns!

We did our New road trip at the end of October and missed peak foliage. Nonetheless, we were still able to enjoy the colors of nature. Peak foliage varies year to year so use this foliage tracker to help you plan your fall road trip.

Table of Contents

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New England fall road trip itinerary

Day 1: drive from boston to maine with a pitstop in salem, massachusetts.

In order to avoid traveling from a different city or state the day our flight left from Boston, we decided it would be best to just head right to Maine and enjoy Boston on our final day. It’s just a short 2-hour drive from Boston to Maine, but first I suggest making a pitstop in Salem which is just 40 minutes outside of the city.

Salem’s historic reputation for witchcraft comes from the Salem witch trials of 1692, in which 20 people were tried and executed. Today, Salem is a tourist destination known for its Halloween celebrations, as well as its many attractions.

The city is also home to a number of historic sites, including the House of the Seven Gables, which was built in 1668. It’s one of New England’s most famous landmarks, and it’s also where Nathaniel Hawthorne set his novel “The House of the Seven Gables.”

We only had a few hours in Salem for our road trip, but fell so in love with this charming, spooky city! This may have been one of my favorite stops on our New England fall road trip.

Things to do in Salem, Massachusetts

• Take some pics at the Hocus Pocus filming locations . I mean it is a classic ! Most of the locations are pretty easy to get to, so I’d try to squeeze in a couple while you’re here. Here’s a list of where you can find all the spots.
• Visit The Witch House (The Jonathon Corwin House). It was home to Judge Jonathan Corwin (1640–1718) and is the only structure still standing in Salem with direct ties to the Salem witch trials of 1692. It’s open 7 days/week from 10 AM – 5 PM. Meaning if you have a mid-afternoon flight, this may be the first thing you want to do. Admission is $9 for adults.

• Check out the fun shops— just strolling around the downtown area is beyond pleasant. They have some super neat shops, including plenty of places to get a reading (you know I couldn’t resist!).
• Grab a bite and drink at The Roof . You’ll love this rooftop bar. We were even lucky enough to enjoy it under an eerie full moon! They have tacos, burritos, and bowls served alongside fun cocktails and shooters (or beer if you wish).
• We didn’t have the time, but if all of this hocus-pocus stuff intrigues you and you have some time to spare you can check out the Salem Witch Museum to learn more (adult admission is $16.50, and it’s open daily from 10 AM – 5 or 7 PM depending on the time of year). There are also some really interesting walking tours like the Voodoo, Vampires, and Ghosts Walking Tour or the Salem Night Walking Tour .

Once you’re done enjoying your time in Salem, head to your hotel in Portland. It’s just a little over an hour’s drive! We stayed at the Holiday Inn Portland – By the Bay .

🏨 Book your stay in Portland

With a great location in Portland, and just a short drive from Salem, Holiday Inn Portland By the Bay is the perfect place to stay in Portland!

Day 2: Portland, Maine

I’ve heard plenty of great things about Portland, and it lived up to the hype! I would love to go back to experience it during the summer months.

Portland is a diversified coastline area that welcomes guests with a variety of unique Maine experiences. You have access to it all—shopping, sailing, beaches, amazing restaurants, and more. This metropolis with a small-town feel is a cultural hotspot and a nature lovers’ paradise. It is home to craft breweries, ocean cruises, and a renowned culinary and cultural scene.

For the most part, we just took ourselves on a self-guided foodie tour and enjoyed strolling around this charming coastal city.

Things to do in Portland Maine

• Grab a cup of joe from  Bard Coffee . We were able to walk here from our hotel, and the weather was an absolute dream. The coffee was delicious! The inside wasn’t open at the time due to COVID restrictions, but it worked out because we snagged our coffee and strolled down the cobblestone streets to the next spot.

• Just a hop skip and a jump away from Bard Coffee is The Holy Donut (they have 3 locations, we went to the one on Commercial Street). This beloved local family-owned spot sells potato donuts with unique variations such as pomegranate, honey lavender, blueberry lemon, and several more! (It’s so funny to me that donuts seem to be just as much of a craze in Portland, Oregon as they are in Portland, Maine.)

• Visit Maine’s oldest lighthouse, the Portland Head Light at Fort Williams Park . With more than 90 acres of open space for enjoyment, there are options for picnics, kite flying, arboretum tours, cliffside loop walks, and exploring the rocky coastline. If you come hungry there are four food vendors (including Cousins Maine Lobster) selling lobster rolls, sandwiches, hot dogs, and gelato. The sights here were extraordinary. This ended up being my favorite thing we did in Portland!

• Grab some chowder and a lobster roll from Luke’s Lobster . You’ll love enjoying these Maine classics with stunning waterfront views. If you’re really hungry you can even order a whole steamed lobster!

• Check out some breweries and distilleries. We visited Oxbow Blending & Bottling  which offers a wide variety of draft and bottle beer from Oxbow and other guest breweries, as well as a unique collection of wine and Amaro. Next door is Hardshore Distilling where you can find some of the greatest and smoothest gin! I was shook at how good it was just to sip on, but they also can make you some fun cocktails with it if you’re not a sipper.
• Grab some frites from Duckfat which is conveniently located right outside of Oxbow Blending & Bottling. They offer a small menu that includes Belgian-style Frites that are hand-punched and twice-fried in duck fat.

Day 3: New Hampshire | Conway, Lincoln, and White Mountain National Forest

The drive from Portland to the White Mountain Forest is just a little over 2 hours. Driving through New Hampshire was an adventure on its own, we were in awe at the colors! Anything that piqued our interest we would just pull off and enjoy.

Because we had such limited time on this trip we did try to cram in as much as we could, however, I know this is only a glimpse into the many amazing fall activities to do in New Hampshire.

Things to do in New Hampshire

• Drive the Kancamagus Highway , a 34.5-mile road trip through New Hampshire’s White Mountain Forest ! The views are stunning; it’s worth taking your time here just to enjoy them. In addition to this scenic road trip route being amazing by itself, there are several points along this route where you can stop off at scenic overlooks with great photo ops.

• Lower Falls is one of the more popular scenic stops along the Kancamagus Highway. There is parking, a picnic area, and restrooms located here. During warmer months people can be found taking a dip in the watering hole.
• Just a few minutes drive separates you from the Albany Covered Bridge . The stream flowing beneath it and fall foilage surrounding it make it another amazing stop on the Kancamagus Highway.

• Eat dinner at The Common Man in Lincoln. We overstuffed ourselves, but it was worth every bite. Their Nantucket pie which includes shrimp, scallops, haddock, and Maine lobster meat baked with lobster cream sauce and seasoned Ritz crumbs gave me life.

We didn’t have time for hikes, but there are so many great ones in the area I definitely hope to have time for our next trip! Here are some popular ones along Kancamagus Highway you may want to check out:

• Diana’s Baths (1.3 miles)
• Flume Gorge (2.2-mile loop)
• Smugglers Notch State Park (several trails to choose from here)

We stayed overnight in Lincoln at the Holiday Inn Express & Suites Lincoln East – White Mountains . Holiday Inn Expresses are usually a little more affordable and always include breakfast which I love. It’s a great way to save a couple of bucks during your New England road trip.

Related read: This southeast USA road trip itinerary , Utah road trip itinerary , and Arizona road trip itinerary are three other great fall road trip options!

Day 4: Vermont | Stowe, Waterbury, and Burlington

Stowe, Waterbury, and Burlington are all great places to visit in Vermont in the fall! Stowe is a little less than 2 hours from Lincoln and has lush forests and rolling hills. A quick 20-minute drive from Stowe gets you to Waterbury which has charm, history, and beautiful valleys.

Just another 30 minutes outside of Waterbury you’ll find yourself on the eastern shoreline of Lake Champlain in Burlington, where Ben & Jerry’s originated.

Things to do in Vermont

• Drive around and admire the beauty of Stowe . Check out the Percy Farm Corn Maze . Don’t be intimidated when they make you exchange phone numbers in case you get lost. It was definitely one of the more challenging corn mazes I’ve ever done, but we made it out in a half an hour!

• Sip on cider slushies and hard cider at Cold Hollow Cider Mill in Waterbury . And of course, you can’t leave without snagging some cider donuts!

• Visit one of Vermont’s cutest gems, Burlington . Church Street Marketplace is an adorable award-winning pedestrian mall home to over 100 shops and restaurants, as well as year-round events, entertainment, and more! We enjoyed lunch at Leunig’s Bistro (the beef bourguignon was phenomenal) and drinks at Foam Brewers , Fiddlehead Brewing Company , and Shelburne Vineyard before heading to our hotel for the night.

Sometimes I reflect on how much we did in one day and it’s kind of wild. We covered three cities and didn’t feel rushed. Makes me second guess complaining there’s not enough time in the day when I can’t get 3 tasks done. We did only get just a taste of them (literally and figuratively), but I feel like what we did and saw were some of the best things to do in Vermont .

We ended up stopping at Molly’s Restaurant in Hanover and staying at Holiday Inn Express & Suites Manchester-Airport . It was 2 1/2 hours away from Burlington and less than an hour away from Boston (where we were heading the following morning).

Day 5: Boston

The final stop on our epic New England fall road trip! Boston is a pretty big city, with plenty to eat, see, and do and flooding with history. I’ve visited twice and don’t even feel like I’ve seen half of what this city has to offer yet! I’ve compiled a few of my favorite things to do in Boston, as well as some things that are still on my list!

Things to do in Boston

• Check out Beacon Hill— This is one of Boston’s most picturesque neighborhoods. The streets are lined with Federal-style and Victorian brick row houses lit by antique lanterns. Acorn Street is located here and it’s one of the most photographed streets in the city. Why you ask? It’s a charming original cobblestone street— something you don’t come across too often nowadays.
• Fenway Park— Go for a game, or just to snap a pic in front of this iconic spot. It’s the oldest of all current major league ballparks!
• Boston Public Library — The Boston Public Library is located in Copley Square, and let me tell ya it’s a stunner. If you’re like me and love a good library, it’s up there for one of the most beautiful and historic I’ve ever been to.

• Do a whale watching tour— If you are visiting Boston during whale watching season (April-October) then a whale watching tour is a must! Enjoy spotting humpback and fin whales, along with Atlantic white-sided dolphins from your high-speed catamaran.
• Freedom Trail — One of Boston’s most iconic things to do! Follow 2.5-mile Freedom Trail that leads to 16 nationally significant historic sites including Paul Revere House (the oldest remaining structure in downtown Boston), Boston Common (America’s oldest public park), Old State House (the oldest surviving public building in Boston), the Old North Church (if you have time, tour the crypt!) and several other historical locations. If you want to get the most out of your experience, they offer affordable guided tours !
• Prudential Center — Enjoy shopping and eating at this gorgeous enclosed shopping center. I especially recommend checking out Eataly! Copley Place is another stunning shopping center located right next door.
• Visit Cambridge— Wander Harvards’ campus, eat and play trivia at The Asgard, or check out one of their fun speakeasies A4cade (located in a grilled cheese shop and full of games) or Brick and Mortar (we actually really struggled to find this one!).

If you want to explore the city in a unique way check out Boston Duck Boat Sightseeing City Tour . You get to tour the city in a renovated World War II amphibious vehicle. The tour begins on the streets and then is taken to the Charles River for a view of the city by boat.

🚌 Hop-On Hop-Off Trolley Tour

If you want a tour that allows you to get off and enjoy some of the stops while also receiving historical info and fun facts check out this 14-stop tour is for you.

Where to eat and drink in Boston

Here are some of my favorite bars and restaurants we got to experience in Boston!

• VERSUS — a super fun arcade bar!

• Citrus and Salt — a Baja-inspired restaurant with Mexican eats and fun, creative cocktails.

• Terra at Eataly—delight yourself with amazing Italian food and craft cocktails in this stunning eatery.

• Legal Sea Foods — best (ok, and only) whole lobster I’ve ever had! It was so unbelievably good, one of the best parts of it is the shrimp & scallop stuffing it was filled with. Also, let’s take a moment to admire all of the lobster in the lobster bisque. They have several locations throughout Boston.

• Trident Booksellers & Cafe —This place is so cozy and especially nice on one of Boston’s dreary days. Come here for good coffee and a good breakfast, and leave with a new book!

We didn’t get to check it out, but the Samual Adams Brewery is located in Boston too!

Are you ready to experience this epic Boston to Maine New England fall road trip?!

If you are looking for a road trip to do in the fall, New England is one of the best. From Boston to Portland, Maine and each stop in between has so much to offer. From beautiful views of rivers, falls, and mountains to great food and fun activities. I hope this post has given you some ideas for your epic fall road trip!

Destiny Snyder is a passionate travel blogger and content creator based in the Tampa Bay area. Originally from a small town near Toledo, Ohio, Destiny's love for exploring new places began when she moved to Florida in 2017. She enjoys uncovering hidden gems, sharing insider tips on the best things to do, places to eat, and coffee shops to visit in every destination. With her blog Guided by Destiny and niche sites Sunkissed in Tampa and Sunkissed in St. Pete, Destiny aims to make trip planning stress-free and fun for her readers.

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If I follow this itinerary what states am I staying in what nights ? Thank you .

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Boston To Maine Road Trip Itinerary (2-3 Days)

• By TripMemos Team
• April 29, 2024
• In USA Travel

When Boston traffic snarls to a stop, you may be thinking: road trip. It's time to escape the big city life for the beauty of Maine. Keep reading for an easy 2-3-day road trip that will restore your soul.

On this 2-3-day-Boston to Maine road trip, you will see Penobscot Bay from the top of Mount Battie in Camden, sail out of Boothbay Harbor, and enjoy the gorgeous views from a historic inn. You will soak in the beauty at the Coastal Maine Botanical Gardens and stroll the Marginal Way with its spectacular ocean views and white sand beaches in Ogunquit.

Traveling this Boston to Maine Road Trip will cover 400 miles. You will be transported into the rocky wonder of "The Pine State" Maine. Keep reading for options for a 2-3-day trip with things to see, places to stay, and good food to enjoy.

How Long is the Trip from Boston to Maine?

The Maine southern border community of Kittery sits 67 miles from Boston. Take I-95 North 48 miles to the New Hamshire border past the town of Seabrook, New Hampshire. Kittery is only 19 more miles north on I-95. Camden, Maine sits 105 miles north of Kittery for a total of 191 miles from Boston.

Where Should We Stop between Boston and Maine?

Your Maine road trip should include some of the historic and scenic harborfront sea towns of Maine. For this road trip, you will drive out to Camden by freeway, then take local roads back south to Boston. You will get to explore Camden, Boothbay, and Ogunquit, Maine. 

Should We Visit Acadia National Park in Bar Harbor?

Acadia National Park near Bar Harbor, Maine should be on everyone's bucket list. The National Parks Service lists Acadia as the 8th most popular national park with over 3.3 million visitors a year. Acadia, with its spectacular mountains and flowing water, deserves its own separate weekend road trip.

Start the Boston to Maine Road Trip with Camden, Maine

What's the best time to leave on a road trip.

You and your road-tripping friends/family should decide together when is the best time to begin your road trip. If you leave Friday night after work, you can have more time to see the sights. If you leave first thing Saturday morning, you can save money on the hotel. It is purely a personal decision.

First Stop Camden, Maine

Whether you leave Boston Friday night or early Saturday morning, head to Camden, Maine. You will drive 191 miles up I-95 and US-1 to Camden.

Camden began as a shipbuilding town named after Charles Pratt, the first Earl of Camden (England), in 1791. Today Camden is a scenic seaside town with great inns, delicious seafood restaurants, with a picturesque waterfront for strolling.  

Picnic in Camden Hills State Park

Begin the fun part of the road trip with a picnic in Camden Hills State Park. Pick up some deli sandwiches and a lobster roll (if you've got a cooler) at the Camden Deli . You can hike, bike, cross-country ski, and camp inside a park.

The Sights from Mount Battie

Camden Hills State Park's premier sight is the top of Mount Battie in the southern section of the park. You can drive to the top of Mount Battie on Mount Battie Road.

Many prefer to hike to the top instead. You can take the 2.4-mile Carriage Trail which winds through splendid forests to the top. Or you can challenge the rocks themselves on the moderate to strenuous 750-foot climb on the Mount Battie Trail. 

Great Hikes in Camden Hills State Park

Take the mile-long moderate hike on the Megunticook Trail up to Ocean's Lookout where you can look down on the cars in the parking lot on Mount Battie. Head to the western part of the park to hike the mile-long Maiden Cliff Trail that winds 800 feet about Lake Megunticook

Downtown Camden, Maine

After exploring Camden Hills State Park, drive into Camden for a relaxing stroll downtown. See the High Street Historic District with 50+ homes and inns from the 19th century. Many have beautiful gardens to enjoy.

Find a great casual restaurant for an early dinner. Head to Sea Dog Brewing for great local beers, burgers, and nachos. For a delicious farm-to-table dinner, head to Blaze Camden for burgers and wood-fired pizza.

Drive South to Boothbay Harbor 

After dinner in Camden, the road trip continues with a short 90-minute (61 miles) drive down the coast to Boothbay Harbor for the night.

Boothbay Harbor has long been a deep port harbor with a strong connection to fishing, lobstering, and sport boating. Locals refer to Boothbay Harbor as "The Boating Capital of New England" for its many marinas and yacht clubs. 

Great Inns of Boothbay Harbor

Before leaving on your Boston to Maine Road Trip, make a reservation in Boothbay Harbor at one of their many beautiful inns.

You could choose a 19th-century sea captain's home at the Bayside Inn with its waterfront views and a short walk to town. During the warmer seasons, you could enjoy a resort experience with a pool and beach at the Smugglers' Cove Oceanfront Inn.  

Remember to check all websites to see what is open year round and what is only open seasonally.

Sailing on Boothbay Harbor

Your road trip won't be complete without a sail on the bay. Reserve with Eastwind Schooner  to enjoy a fully-crewed charter. For the more adventurous take sailing lessons with Midcoast Sailing to see the open water with a sheet (rope) in your hand and to stand at the helm (wheel) guiding the sailboat.

Lunch in Boothbay Harbor

After a great morning on the water, sit at the picnic tables at Shannon's Unshelled , "Fresh from Trap to Table,"  for some of the best lobster and french fries at this walk-up joint. Another great lunch spot is the relaxed bar Brady's with all types of seafood, burgers, and comfort food—Maine Pot Roast! 

Coastal Maine Botanical Gardens

From Boothbay Harbor, head inland for 4 miles to see the wonderful gardens of the Coastal Maine Botanical Gardens.

Wander through over 300 acres of flower gardens, a children's garden, a hillside garden, and more. Visit the Native Butterfly and Moth House to sit and be soothed by the colorful residents as they alight on you looking for nectar.

The 2-Day Boston to Maine Road Trip

Let the Coastal Maine Botanical Gardens be your final activity if you are on a 2-day Boston to Maine road trip. Head south for 2 hours (94 miles) for a final dinner in the quaint sea town of Ogunquit, Maine. After dinner, you've got just 72 more miles of freeway driving back home to Boston.

Great Dinners in Ogunquit, Maine

Head to The Front Porch in Ogunquit, for three dining experiences: the main dining room, the bar+lounge, or the lively sing-along piano bar.

Another fun option is freshly all made-in-house ingredients for New York-style pizza at Lapizzeria . Or head to dinner at That Place in Ogunquit for delicious steaks and seafood dishes in a lively bar atmosphere.

The 3-Day Boston to Maine Road Trip

If you are lucky enough to do a 3-Day Boston to Maine Road Trip, spend your last day in Ogunquit, Maine. You can stay in a historic B&B like The Trellis House or a beautiful inn like the Nellie Littlefield Inn & Spa or the Gazebo Inn with its swimming pool and spa.

Great Brunch in Ogunquit, Maine

On the last day of your road trip, sleep in then head out for brunch done right. Try the Egg and I Pancake and Waffle House or The Greenery Cafe for the full brunch experience of eggs, hash, french toast and so much more. For coffee and freshly made croissants or pastries, head over to Mornings in Paris for a taste of Europe.

The Marginal Way in Ogunquit, Maine

The "high" point of any visit to Ogunquit is strolling the cliffside paved walkway above the beaches and rocky shore on the Marginal Way . This 1.5-mile trail passes historic homes and scenic inns. You will have amazing views from all sides.

Small parking lots are available at each end. You may find street parking easier as there are many accesses to the trail. Benches are scattered along the way for looking down at the ocean. Sturdy stairs bring you down to the different beaches.

Perkins Cove in Ogunquit, Maine

Conclude your 3-Day Boston to Maine road trip with the picturesque Perkins Cove . This former artist colony now includes great restaurants, shopping, art galleries, and scenic overlooks.

Perkins Cove sits on a peninsula with the ocean on one side and the cove on the other. A beautiful white pedestrian, stroller, and bicycle drawbridge connect Perkins Cove to downtown Ogunquit.  

The 2-3 Boston to Maine road trip has barely scratched the surface of all that the Pine State has to offer. As you explore, take the time to stop to see something that catches your eye. Share your road trip finds in the comment section below.

Boston is awesome, but Maine is calling you.

Check out these other awesome road trips:

Four Best Road Trips from Florida to Other States

5-Day Colorado Road Trip Itinerary

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Boston to Bar Harbor Maine Road Trip (6 Days)

We recently decided to tackle the unforgettable journey along the stunning Maine coast on a Boston to Bar Harbor Maine road trip. It was one of the best road trips we’ve been on in a long time. This 300-mile adventure takes you through charming towns, along rocky coasts, and past picturesque lighthouses. It’s gorgeous, it’s laid back, and it’s a perfect summer road trip.

While the whole drive takes only five hours, you can make it as quick or as slow as you want by blowing past or stopping by as many attractions and towns as you like. Our full trip was 6 days in length and had us indulging in fresh lobster, walking through small towns, and taking in the stunning views of Acadia National Park.

» Looking for a trip that is a bit shorter? Try this Boston to Portland Maine Road Trip .

I guarantee this epic Boston to Bar Harbor adventure will be a memorable one. All you need is your car, online maps, and a sense of adventure. Let the road take you where it will and enjoy!

Table of Contents

Planning Your Route

When we started planning our Boston to Bar Harbor road trip, we realized there are several routes you can take, each with its own attractions and scenic drives.

Route 1 is a popular option for those looking to take a scenic drive along the coast. It passes through several charming coastal towns, including Portsmouth, Ogunquit, and Kennebunkport. The drive takes about 5 hours without any stops.

This is the route we took to get up to Bar Harbor. We stayed in Boston the first night, Portland the second night, Belfast the third night, and Bar Harbor the last night.

On the way back, we took I-95, because we just needed to get back to Boston for our flights home.

This is the faster route. It’s a straight shot from Boston to Bar Harbor, taking about 4 hours without stops. Note that while this route is faster, it’s not as scenic as Route 1, and you won’t go through any of the cute towns that make this road trip so special. So I would avoid this route, unless you’re in a hurry, but then why are you calling it a road trip?

Route 3 is another scenic option that takes you through the White Mountains of New Hampshire and into Maine. It’s a longer route, taking about 6 hours without stops, but it offers some stunning views of the mountain range.

6-Day Road Trip Itinerary

Boston, massachusetts (day 1).

After arriving in Boston, Massachusetts , you can jump directly into the first day of your road trip or spend the night getting a fresh start the next morning. So drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, classic sports bars meet a thriving theatre scene around every corner. While there’s no way to see the best of Boston in one day, you can include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem to Portland, Maine (Day 2)

Your second day involves the first stretch of road to tackle. Heading north on I-93/I-95. It’ll take about 35 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. Here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

Portsmouth, NH

When you’re done exploring spooky Salem, take I-95 or Route 1 north to Portsmouth, New Hampshire. This is a cute little town that deserves a lunch-time stop. It takes about an hour to get there from Salem.

We walked around the town and waterfront for about 30 minutes before heading to lunch. Here are a few shops we enjoyed in Market Square on Congress Street:

• G. Willikers Toy Shop
• Diversions Puzzles & Games
• Sea Love Portsmouth
• The Spice & Tea Exchange

We went to Geno’s Chowder & Sandwich Shop for lunch. This is a great place to go in the summer, but it’s closed through the fall and winter. If you need an alternative, go to Row 34 .

After leaving Portsmouth, if you go up Route 1, you can dip off the road on 1A to see the Nubble Lighthouse.

Nubble Lighthouse

Perched on a rocky islet off the coast of York, Maine, the Nubble Lighthouse serves as a sentinel guarding both history and stunning vistas. Built in 1879, this iconic lighthouse stands against the dramatic backdrop of the Atlantic Ocean. Just note that you’re only going to capture it through your camera lens or simply soak in the view, because no one is allowed on the island. All you can do here is park and gawk.

Next, head back up to I-95 or Route 1 to Ogunquit. We loved this little town, however bad the traffic was to get through it. You can park in a side-street lot and walk to the center of town (it’s very small).

Stop in a few shops, like Revelations Gift Shop, Cricket’s Corner, and Sea Bags. Grab a coffee at OGT Beanery or an ice cream at Sweet Pea’s Ice Cream. Then take a walk down Wharf Lane to where you can see the popular Main Beach across the water. If you have time, you should definitely plan to spend a little time on the beach. There’s a great shallow bar and inlet that you can swim in.

After Ogunquit, you can head up to Portland on I-95 or continue along Route 1, which will take you through Kennebunk, or if you branch off on State Route 9, you’ll go into Kennebunkport.

Kennebunkport, Maine

We really enjoyed Kennebunkport. It’s one of the most quintessential New England towns with its historic architecture, scenic coastline, and vibrant arts scene.

The town is well-known for its maritime heritage, which you can explore through boat tours and the bustling Dock Square. Beyond the obvious, the town surprises you with hidden coves and tranquil beaches, making it more than just another tourist spot on the map.

However, there are a lot of tourist shops to pop into like the Lobstore, Beach Grass, and Copper Candle, and Good Earth. All very cute. If you’re getting hungry, grab a lobster roll at the Clam Shack (which is closed during the off season).

For a drink, we really enjoyed Batson River Brewing & Distilling, which has a lovely outdoor area as well as inside space in the house, and a huge upper balcony.

Old Orchard Beach

Old Orchard Beach is a popular coastal destination you can stop at on the way to Portland that has a lot of seaside charm.

One of the main attractions in Old Orchard Beach is its beautiful beach. The beach is over seven miles long and offers plenty of space for swimming, sunbathing, and relaxing. You can also rent beach chairs and umbrellas, as well as bicycles, to explore with.

Another popular attraction in Old Orchard Beach is the classic boardwalk. The boardwalk is lined with shops, restaurants, and amusement park rides, making it a great place to spend an afternoon or evening. Speaking of amusement park rides, Old Orchard Beach has the last surviving beachfront amusement park in New England. There are arcade games, a Ferris wheel, and of course plenty of iconic Maine lobster rolls.

Be aware that parking is atrocious here. You’ll pay at least $20-30 to park in one of the lots. We found no street parking.

Portland, Maine (Day 3)

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

• Visit Fort Williams Park and the Portland Head Light
• Do a brewery tour of Portland to visit some local craft breweries (we also did our own walking tour of the breweries (there are a ton in East Port)
• Shop the local boutiques and specialty shops of Old Port
• Grab a sunset view along the Eastern Promenade

Tours to look out for while you’re in Portland:

• Old Port Culinary Walking Tour
• Cusco Bay Sea Kayaking Tour
• A Walk Through Time Tour in Portland 

East Port is known for it’s great food and drinks, and is the perfect place to stop for refreshments. There are several distilleries and breweries to choose from.

Hardshore Distilling Company was our favorite. We enjoyed a tasting of a few of their gins. We happily grabbed a cocktail and some duck fat frites from the frites shack next door and sat out on the patio. The perfect way to spend a summer evening in Maine.

Where to stay: Portland Regency Hotel & Spa

Portland to Belfast (Day 4)

You can drive straight from Portland to Bar Harbor if you’re in a hurry to get there, but we wanted to take one extra day to hit up all the fun little stops between the two. For this reason, we decided to stop over for the night in Belfast, which I think was a great idea because there were lots of fun things to do there. Mind you, there are not a lot of great places to stay in Belfast, so if you want a higher-end hotel you’ll have to go on to Bar Harbor for that.

Here are the stops I suggest making on the way:

• Brunswick – Sea Dog Brewing Co opens at 11am, located on the waterfront, a must-try while in Maine. Try the Blueberry beer.
• Wiscasset – Red’s Eats is an iconic lobster stand with a HUGE line at all times. We actually ate across the street at Sprague’s, which had more seating and a shorter line. The crab roll was amazing.
• Waldoboro – Odd Alewives Farm Brewery. If it’s time for a beer, try this place that makes Maine farmhouse ales.
• Rockland – Maine Lighthouse Museum  
• Owls Head State Park – With its historic lighthouse, rocky coastline, and dense woodlands, the park delivers a dose of New England’s natural beauty and maritime heritage.
• Camden – Bald Mountain is the fifth highest peak on the eastern seaboard (beautiful views from the top), Barren’s Brewery & Distillery (great place to grab a drink right on the water).
• Belfast – Young’s Lobster Pound (fun place to eat)
• Belfast – Marshall Wharf Brewing Co – fantastic beer list, fun locations and good live music.

Where to Stay: Fireside Inn & Suites

Bar Harbor & Acadia National Park, Maine (Day 5-6)

This part of the trip is likely what you’ve been looking forward to the most. Acadia is consistently one of the most-visited national parks in the United States. It receives around 3.4 million visitors per year. When planning your trip, you’ll want to tack on as many days here as you want for exploring, hiking, and other activities. I would recommend spending at least 2 full days in Bar Harbor (more if possible).

Acadia National Park

Start your day with an hour and a half drive to Bar Harbor. Along the route, you’ll pass through a few towns worth a stop. After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park.

On Maine’s largest island, Mount Desert Island, the 47,000-acre park boasts imposing mountains, picturesque lakes, and endless miles of hiking trails.

An entrance pass is required for all visitors. It’s $35. You can also use your America the Beautiful annual pass, if you have one. Vehicle reservations are also required for Cadillac Mountain. You can’t go up there without a reservation. Make it well in advance during peak times to make sure you get the time you want.

The top three things to add to your Acadia itinerary include:

• Hiking to the summit of Cadillac Mountain
• Kayaking on Swan Lake
• Biking or driving the Park Loop Road

Where to stay: Atlantic Oceanside Hotel or Holiday Inn Bar Harbor

Acadia NP is one of the main reasons people visit Bar Harbor, but that doesn’t mean you should skip Bar Harbor itself. It’s a small town that has a lot to offer. It can, however, get really crowded in the summer, so getting in and out of town in a car can be very tedious. Take a taxi or hotel shuttle bus, if you can.

The town’s quaint streets are lined with unique shops and eateries, inviting you to explore local flavors and crafts. One of the fun things to do is take a scenic cruise around Bar Harbor. Many of the restaurants are touristy, but still good. We ate at Geddy’s (decent) and CIAO food|drink (outstanding).

There are also a few breweries that we checked out: Atlantic Brewing Midtown and Fogtown.

Returning to Boston

After exploring the stunning coast of Maine, it’s time to head back to Boston. You may be feeling a bit tired after all the driving and sightseeing, but keep in mind that it’s an almost 5-hour drive back to Boston. You’ll likely have to get up early and hit the road in order to get back for your flight.

We took I-95 on the way back because it’s the fastest route.

How long does it take to drive from Boston to Bar Harbor?

The driving time from Boston to Bar Harbor is approximately 4-5 hours, depending on traffic and any stops you make along the way. The route takes you through scenic coastal Maine, so you may want to allow extra time for sightseeing and exploring the quaint towns along the way.

What is the distance between Boston and Bar Harbor?

The distance between Boston and Bar Harbor is approximately 280 miles. The route takes you through New Hampshire and along the Maine coast, offering stunning views of the Atlantic Ocean and charming coastal towns.

Are there any ferries from Boston to Bar Harbor?

There are no direct ferries from Boston to Bar Harbor, but you can take a ferry from Portland, Maine to Bar Harbor. The ferry ride takes approximately 3 hours and offers stunning views of the Maine coastline. Alternatively, you can drive from Boston to Bar Harbor or take a bus or train to nearby towns and then rent a car to drive to Bar Harbor.

How many days should I spend in Bar Harbor on a road trip from Boston?

The ideal length of time to spend in Bar Harbor on a road trip from Boston depends on your interests and schedule. If you want to explore Acadia National Park and the surrounding area, you should plan to spend at least 2-3 days in Bar Harbor. This will give you enough time to hike, bike, kayak, and explore the charming town of Bar Harbor. If you are short on time, you can still enjoy the highlights of the area in a day trip from Boston, but you will miss out on some of the more scenic and remote areas of the park.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

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Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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A family-focused road trip through southern Maine

Make boston your starting point on this summer adventure..

There’s a reason they call it Vacationland. Coastal Maine is full of quaint seaside vignettes, charming fishing villages, and rugged, rocky landscapes that make for an ideal family getaway .

It would take countless summers to fully plumb the depths of Maine’s coastal offerings, but a three-day road trip will give you a good survey of the scenic beauty and small-town appeal that led to the state’s slogan: “the way life should be.” Here’s how to tackle a three-day drive up the coast, kids in tow.

MORNING: Coastal strolls and killer brunch

Get an early start out of Boston—you’re making your way to Maine, and you need to beat the summer traffic. Vacation officially begins as soon as you see your first “Moose Crossing” sign on the Maine Turnpike (just don’t tell the kids you’re about as likely to spot a moose in Kittery, ME as you are back home). If you need to stretch your legs on the way, make a morning stop at the Rachel Carson National Wildlife Refuge in Wells for an easy stroll through the forest, which runs along a tidal marsh.

Travelers say: "The Rachel Carson National Wildlife Refuge is a beautiful, peaceful place to go for a walk. The trail is kept clear and is accessible, with only one small slope within the one-mile loop. There are spots to stop, some with benches, to take in the beauty of the refuge and often to spot some wildlife. When we stay in Wells, this is a daily activity for us." —@Denham33

Afterward, it’s back on the road and Biddeford bound. Put your name in at the worth-the-hype Palace Diner , then take a walk while you wait. Elements: Books Coffee Beer makes a mean maple latté, but if the day is already heating up, try the Biddefizz, an Americano over ice topped with a splash of tonic.

When your seats open up at Palace Diner, be sure to order the French toast—the pillowy soft brioche with a crispy, caramelized surface is a strong contender for the best French toast in Maine, if not all of New England.

If it’s open, swing by Lorne on your way out of town. This cheerful, pretension-free little wine shop specializes in low-intervention bottles, and the friendly staff can recommend something that pairs nicely with beachside lounging. Next up: a short jaunt to Portland.

AFTERNOON: A lobster boat adventure

You’ve made it to Portland, Maine’s biggest metropolis. If you’ve worked up an appetite, make a pit stop on Washington Avenue in Munjoy Hill for provisions. Grab hoagies from the excellent Ramona’s , a grain salad and a container of Dear Dairy ice cream from The Cheese Shop of Portland across the street, and a sourdough chocolate chip cookie from the fermentation whizzes at Onggi down the block.

Otherwise, go straight to the Old Port. You’re heading out on the water with Rocky Bottom Fisheries aboard the F/V Wild Duck for a lobstering primer, during which you’ll learn the ins and outs of hauling and baiting traps, measuring “keepers,” and tossing back stray crabs. Rocky Bottom is family-owned, and their team makes the lobstering experience a blast for even the littlest passengers. Plus, it’s hard to beat the photo op of a kid in a bright-orange lobsterman’s apron, lobster in hand and the famed Portland Head Light in the background.

EVENING: City walks and good eats

Soak up golden hour with a walk around the Old Port. Don’t miss Portland Dry Goods for chic-but-easygoing apparel; Browne Trading Co. for an Eric Ripert- and Ruth Reichl-approved selection of tinned fish, caviar, and other gourmet goodies; and Blanche and Mimi for upscale flea market vibes and a small-but-mighty selection of children’s clothing and accessories.

For dinner, it’s dealer’s choice: Linger around the Old Port before wandering over to Lenora for tacos and micheladas (or aguas frescas for the under-21 crowd), or stroll downtown for charcuterie, small plates, grandma slices, and a stellar wine selection at the laid-back Friends & Family .

MORNING: Breakfast and botanical gardens

There’s no shortage of excellent a.m. options in Portland, so choose your own adventure based on where in town you’re staying. West Enders should head to Tandem Bakery for the best biscuits north of the Mason-Dixon and the top breakfast sandwich on the eastern seaboard (no, really). Near the Old Port, hit up Bread and Friends for decadent scrambled eggs, flawless Viennoiserie, and loaves made with house-milled grains.

Travelers say: "We heard about long lines [at Tandem] and almost didn't go, but saw we can order online for faster pickup. When you check in at the pickup area, your food is ready and they give your coffee order priority so it's fresh made. We had a couple biscuit dishes (a sweet and a savory), which were excellent. We also had a scone that easily was one of the top two we've had anywhere. ...There is a nice outdoor seating area with communal picnic tables." —@sunhead

Then it’s time to hit the road. Follow Route 1 up the coast for plenty of dreamy scenery. Along the way, make a detour to the Coastal Maine Botanical Gardens in Boothbay. Kids will get a kick out of the fairy village, children’s garden, and massive troll sculptures scattered throughout the forest (plus activities like story hours and puppet shows), while adults will appreciate the scenic pathways and the chance to let little ones safely run off some energy.

AFTERNOON: Lobster rolls, old-school rides, and lighthouses

Lobster in Maine is obligatory, so drive another hour up the coast for lunch at the waterfront McLoon’s Lobster Shack in Spruce Head, where you’ll find what devotees claim is the best lobster roll in Maine. (All we’ll say is that a side of warm melted butter for drizzling is gilding the lily in the best way.) Don’t leave without trying the blueberry bread pudding à la mode .

If you’ve got a kid who appreciates all things engine-powered, drive 15 minutes north to the Owls Head Transportation Museum , a collection of cars, planes, bicycles, and more, all built before 1940. Older kids will like the thoughtful historical exhibits; younger ones can gape at all the colorful things that go vroom .

Before you leave town, stop by the Owls Head Lighthouse —it's situated on a scenic point and houses a small museum. Look out for the tiny headstone marking the final resting place of longtime lighthouse dog, Spot.

EVENING: Dinner and local wine

For dinner, you’re Camden bound. This sweet little port city punches above its weight when it comes to restaurants. Take your pick between excellent Thai food at Long Grain or pizzas at Wolfpeach . Before retiring for the night, swing by the Oyster River Winegrowers storefront and pick up a bottle of Maine-made wine to crack open once the kids are in bed—the Morphos pet-nats are cult favorites.

MORNING: Main Street shopping and a Mount Battie hike

Grab a quick breakfast and a cup of coffee at Zoot . You’re heading to the top of Mount Battie today, but if you’re itching to do a little shopping, now’s the time. Camden’s main drag has several strong options: Goods for quirky-cool culinary bits and bobs, Blue Jay Boutique for high-end baby and toddler clothes and accessories, Swans Island Company for wonderfully lush Maine-made blankets and scarves, and Hundred Acres for an impeccable edit of home goods.

Then it’s on to the mountain. Camden Hills State Park offers a network of trails to get you to the top of Mount Battie and its neighboring summits, whether you’d prefer a tough-but-straightforward scramble or a gentler switchbacking route. Either way, the end result is the same: sweeping views of Camden Harbor and the Penobscot Bay.

Travelers say: "We chose to drive [into Camden Hills State Park] and up to the top of Mount Battie, then take short hikes from there. The 1/2 mile path we took was well marked with blue dots, and at almost every turn we were rewarded with a stunning view of Penobscot Harbor. ...You should wear good walking shoes." —@nkdp

AFTERNOON: Oyster shucking or lighthouse hopping

There’s much to see further up the Maine coast, but Acadia warrants its own trip so back south you go. Stop at Seafolk Coffee in Rockport for a pick-me-up with a harbor view (and if they have loaves from Stones Throw in stock, grab one to take home for the week).

Your afternoon plans hinge on one question: Are you oyster people? If so, you’re heading to Glidden Point in Edgecomb for a tour of the oyster farm followed by shuck-your-own oysters on the patio, washed down with a crisp glass of muscadet—or perhaps a blueberry soda, if you’re under 21. If the answer is a hard no, keep driving until you hit Bath, home of the Maine Maritime Museum , where you’ll hop on the afternoon Shipyards and Lighthouses Cruise and breeze down the Kennebec River.

EVENING: Costa Rican cuisine and a walk on the beach

Your Maine excursion is almost over, so it’s time for one last seaside hurrah. Make your final stop just over the Casco Bay Bridge in South Portland. Start with an early dinner at Cafe Louis in Knightville—if you haven’t had Costa Rican food, you’re in for a treat.

After, hit up Red’s Dairy Freeze , a summertime institution that you’ll know by the big white-and-red barn and snaking line. Finally, take your spoils (unless you got a cone, in which case, transport at your own risk) over to Willard Beach for a long walk in the waning light of sunset. Then pile back into the car for your final leg home—and start planning your next visit to Vacationland.

The ultimate family travel guide

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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12 Fantastic Stops On A Road Trip From Boston, Massachusetts To Bangor, Maine

• Destinations
• Massachusetts
• New England
• New Hampshire
• Road Trips In The U.S.
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• United States

Boston is the perfect city to begin this scenic New England seacoast trip. The booming Seaport District, luxury shopping in the Prudential Center, or places to explore Boston’s historic past are all just minutes from Logan International Airport. The busy airport offers a convenient spot to begin your Boston to Bangor road trip. Finish up your adventure in Bangor, a friendly and walkable city. It is home to author Stephen King and local nature-focused experiences that are a nod to Maine’s great forests. 

With a fun rental, maybe a Jeep with a fold-back soft-top or a classic Mustang convertible, you will be off in search of amazing coastal cuisine, unique shopping experiences, perfectly curated craft brews, and coastal fun-in-the-sun adventures.

Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.

1. Boston, Massachusetts

Shopping at the airy Prudential Center , home to high-end brands, is a feast for the fashionista’s eyes. You can find L’occitane, Swarovski, Oakley, and more that will satisfy your desire to own pretty things. When you need to stop for a bite, try Earls Kitchen & Bar or Eataly , both globally well-known establishments. 

History buffs will need to experience Boston’s Freedom Trail . Another great option for exploring the city is the Boston Duck Boat Tour , a unique land and water tour.

Boston is home to many classic, well-known craft breweries. Check out our list of 5 Fantastic Breweries To Visit In Boston to help you decide which one or two you want to visit while you are in town.

Start your trip with a Boston luxury stay. There are a wide selection of great options. The Marriott Vacation Club Pulse is in the renovated historic Custom House. They offer well-appointed suites with panoramic views of the city.

2. Newburyport, Massachusetts

As you begin your trek north, stop for lunch at Bob Lobster in Newburyport. There is always a line filled with hungry locals and visitors, but it moves quickly. Their selection of lobster rolls are fresh and tasty. 

Take a walk around the beach at Plum Island or the Parker River National Wildlife Refuge to experience a coastal habitat for over 300 species of birds and wildlife. 

For more information about visiting beautiful Newburyport, check out How To Spend A Perfect Day In Quaint Newburyport .

3. Hampton Beach, New Hampshire

New Hampshire’s coastline is relatively short when compared to their northern and southern neighbors. However, they jam a tremendous amount of beachy fun in a little package. Hampton Beach is a classic East Coast beach, where aromas of fried food, suntan lotion, and salty air morph together in the quintessential “day at the beach” memory.

The water is chilly, but the beach is wide with a walkway and parking along its length. Hampton Beach is the spot for your road trip beach day.

Get the most out of your Hampton Beach visit with links to all the around town happenings in How To Spend A Perfect Day In Quaint Hampton Beach .

4. Portsmouth, New Hampshire

Portsmouth is a lovely stop along the way to wander through quaint shops, small bistros, and artist galleries. 

Portsmouth Brewery is an anchor in Portsmouth’s bar and restaurant scene. Order a flight to sample a variety of their craft brews at this fun lunch or dinner spot. 

Another great stop is the Salt Cellar , where you can find a wide variety of finishing salts. Try the Black Lava Sea Salt, Lime Citrus Sea Salt, Merlot Wine Sea Salt, and others. They will add the perfect four-star touch to your home-cooked delicacies. 

5. York, Maine

More beachy fun awaits you in York, Maine. Short Sands, York’s main sandy beach, is located in the heart of the action. The beach area offers parking and a busy downtown district with shops and restaurants. Long Sands Beach is another popular York beach. It has sections of rocks to scramble over and a sandy beach area along with on-street parking.

A must-see shop is the Stonewall Kitchen Company Store . Every Stonewall product you love, but can never find at home, is here just for you. Additionally, they offer cooking classes in their onsite kitchen.

6. Portland, Maine

Portland is a seaport city full of history, foodies, and fun. You can spend lots of time wandering the Old Port district exploring wonderful restaurants and quaint shops.

Red Soxs fans will want to take in a game and watch the Portland Sea Dogs . You never know what up-and-coming baseball phenom or rehabbing all-star may take the field.

One must-stop is The Holy Donut . Their mashed potato donuts are making baked goods history. Dine on pomegranate, maple bacon, and sea salt donuts made with fresh Maine potatoes. Sweet treats with healthier ingredients and their daily rotation of flavors will amaze and delight you. 

7. Freeport, Maine

Freeport is home to the L.L. Bean Flagship Store , which is really more like a compound with separate buildings including the Hunting and Fishing Store; Bike, Boat, and Ski Store; Home Store; and the Outlet Store. For the L.L. Bean enthusiast, it is possible to spend an entire day exploring. 

When you are finished shopping, stop at Stars & Stripes Brewing Company and enjoy a fresh craft beer while you ogle over your shopping purchases. 

You can easily spend an entire day in Freeport. How To Spend A Fantastic Day In Freeport, Maine: Shopping, Eating, And Relaxing is full of tips for getting the most out of your visit.

8. Bath, Maine

Bath’s Main Street is an artisan haven. Beautiful historic buildings filled with shops carrying items from Maine’s artists and crafters contribute to the bohemian vibe. 

Stop at Bath Sweet Shoppe for a mid-day, sweet treat. A bag of milk chocolate gold coins or Jelly Belly Red Raspberry Hearts evokes fond childhood memories. 

9. Wiscasset, Maine

Enjoy a leisurely afternoon in historic Wiscasset. Visit the Nickels-Sortwell House , the 1812 Jail , and the Castle Tucker home for a peek into the lives and times of the people of coastal Maine.

Enjoy an al fresco lunch from the legendary Red’s Eats . The line gets particularly long during traditional dining hours, but queueing up for a mid-afternoon meal means less waiting time. 

10. Camden, Maine

Camden’s charming waterfront downtown area is blessed with picture-perfect views. Sailboats grace the snug harbor, which is lined with local restaurants offering on-the-water dining views. 

Maine is known for its lobster, and you won’t find a better lobster roll than at McLoon’s Lobster Shack located on Spruce Head Island. Tucked away in a classic Maine cove is a small red shack that serves up amazing seafood. It is worth the drive; your reward is a beautiful view and a perfectly prepared lobster.

If you have extra time to stay over in Camden, you will find great ideas in How To Spend A Beautiful Weekend In Quaint Camden, Maine . 

11. Belfast, Maine

Belfast is a charming town that rises from the waterfront to a thriving shopping area. The waterfront is busy with fishing and leisure boats making their way out to Penobscot Bay. 

Visit Eat More Cheese to kit out your picnic basket, then grab a bench and enjoy the waterfront views. 

12. Bangor, Maine

Bangor has a cozy, hometown feel wrapped in a sophisticated city that only Mainers can seem to accomplish. A hub for big-name concerts and great food, the hometown of Stephen King, and close to forested wonderment, Bangor is unique.

Waterfront Concerts presents concerts from nine of Bangor’s concert venues. With guests like Thomas Rhett, Jay Leno, Brothers Osborne, Kiss, and others, you can plan your visit around a fun waterfront venue or cozy auditorium.

For Stephen King fans, SK Tours will treat you to a fascinating 3-hour tour of locations that inspired King’s “Derry, Maine,” filming locations, and a view of his private residence. Your guide will enchant you with local tales, and the history of the King family and their many philanthropic contributions to the Bangor area. 

Spend some time hiking and canoeing at Hirundo Wildlife Refuge just outside of Bangor. With 7 miles of hiking trails and peaceful streams, you will find the perfect spot to satisfy your need for nature and a Zen-like moment.

Fine dining couldn’t be finer than at Novio’s . The bistro is tucked away on a side street where those in the know go to dine on sumptuously prepared and gorgeously plated cuisine. The menu changes seasonally and is focused on the restaurant’s own garden-grown produce and locally-sourced proteins. The ramp fritters are a light and flavorful starter. Follow up with the crab pistou with house-made linguini and delicately dressed with a white wine creme fraiche. Save room for dessert, you’ll want to savor the s’mores cheesecake.

Pro Tip: The drive up Routes 1 and 1A offer beautiful coastal scenery and bucolic farmland views. If you are not flying out of Bangor you can head back to Boston on Interstate 95 for a faster, albeit less scenic drive.

Sandi loves writing about culture, cuisine, adult beverages, cruising, golf, skiing, road trips, hiking, New England, and photography. Traveling solo, with hubby Chris, or the entire Barrett clan there is always a story waiting to be told.

• National Parks
• Tiny Houses

Must-See Stops on a Boston to Bar Harbor Road Trip

Posted by Liz Dengler August 09, 2021 Updated June 08, 2023

Maine is arguably the best place to spend your vacation time on the East Coast, with remote and rugged landscapes, numerous farms and ranches, old historic towns, lighthouses, and stunning swaths of coastline.

It’s easy to understand why some people take one trip to Maine and start daydreaming about moving north to live the quintessential New England life. Fortunately, if you’re in Boston, the Boston to Bar Harbor road trip is an easy drive, not to mention a beautiful one.

Here’s the best itinerary for your Boston to Bar Harbor road trip, complete with the best stops for travelers interested in small coastal towns, history, wildlands, beauty, and true New England hospitality.

Related Read:   When is the Best Time to Visit Acadia National Park?

Boston to Bar Harbor By Segment

There are two routes you could take for a Boston to Bar Harbor trip, but if you have time, travel along the coast the entire way. Technically fewer miles (275 versus 285), it does take a little more time (about 5.5 hours instead of 4.75) but is totally worth it.

The trip along the coast is one everyone should do at least once. Visiting the quaint coastal New England towns, enjoying views of the rocky shores, and taking advantage of the numerous opportunities to get out and explore trails or historical sites all make this route well worth the extra time.

If you can, take a few days to make your way along each segment of this trip.

Related Read:   11 Relaxing Swimming Holes in New Hampshire

Segment 1: Boston, MA to Portland, ME

• Distance: 112 miles
• Drive time without stops: 1 hour, 45 mins

For simplicity’s sake, this road trip guide assumes you’ve already explored Boston to your heart’s content and are ready to explore beyond the lands “just outside Boston.” T

his first segment will take you through New Hampshire and into Maine.

Related Read:   The 6 Best Scenic Byways to Fully Experience Massachusetts

Segment 1 Highlight: Portsmouth, NH

When you get to Portsmouth, NH, make sure to stop and explore the town. Fuller Gardens , just south of the city on the coast, is a botanical garden open to the public. The Gardens have a fascinating history dating back to 1927, and the Rose Garden is a must-see.

Your next stop in Portsmouth should be the Seacoast Science Center . This educational detour is located in Odiorne Point State Park . Learn about the oceans and marine life and explore tide pool habitats. You can also sign up for kayak tours, workshops, and family programs, to name a few of many. This is a great first stop to get everyone excited about fun things to come.

Related read : 8 Unique Places to Stay Near Boston When You Need to Get Away

Segment 1 Highlight: Portland, ME

Now here is a city worthy of exploration. Portland, is a fast-growing city on the ocean. The downtown, also called Old Port , is home to all sorts of charming shops and restaurants and sits along the waterfront. You won’t regret taking extra time to spend a day or two in this little city.

Portland Head Lighthouse is always breathtaking. Built in 1791, it’s the oldest lighthouse in Maine and is still active today. However, it now houses a museum about the cape’s history.

If you have the time, look into taking a sail on one of the Portland Schooner Company’s windjammers that leave from quite near downtown. They have several special events through the season, or you can book a standard two-hour public sail .

Related Read:   12 Magical & Unique Places to Stay in Maine

Segment 1 Side Trip: The Crane Estate

About a 30-minute detour from the interstate, the Crane Estate is a great side trip for hiking fans, history buffs, or those fascinated with architecture. The estate began its life as a humble farm in the late 1900s; however, through the preservation efforts of The Trustees , the property was developed into an expansive historic site now open to the public.

The estate has several zones: Castle Hill , Crane Beach , and the Crane Wildlife Refuge . There are historic houses, collections, beaches and trails to explore, and sometimes special events on the weekends. Be sure to pick up a map when you enter.

Segment 1: Where to Stay

You’ll find no shortage of charming B&Bs in either of these towns. At the Crane Estate, you can stay at Lodging the Inn at Castle Hill , a beautiful estate turned inn is rich with history. In Portland, you can check out some of these cute airbnbs or try the beautiful (and pet-friendly)  Inn by the Sea .

If you can’t pull yourself away from Portsmouth, try the downtown Ale House Inn or glam Wentworth by the Sea . Portland has plenty of camping , too.

Segment 2: Portland to Rockland

• Distance: 79 miles
• Drive time without stops: 1 hour, 40 mins

The coastal stretch from Portland to Rockland has so much to do that it’s impossible to recommend everything. The 79-mile stretch of road (92 if you add Popham Beach) is jam-packed with small towns, beach visits, and lighthouses.

The following are only a few suggestions to get you started, but you could easily spend a week exploring everything this segment has to offer. While this is one of the best days on a Boston-to-Bar-Harbor road trip, it also works well as its own separate trip for a few days if you want to see everything in more detail.

Segment 2 Highlight: Freeport

Freeport is undoubtedly a tourist town and is probably best known by out-of-towners for the legendary Flagship L.L. Bean outlet stores. But Freeport has more to offer than just shopping.

You can lace up your boots and explore any of the numerous nearby parks and preserves that offer up great hiking, or grab your binoculars and visit the Mast Landing Audubon Sanctuary , a birding hotspot just a mile from downtown. History buffs in your crew may want to check out the Freeport Historical Society.

Segment 2 Highlight: Rockland

Rockland is directly on the Boston to Bar Harbor main route and is a beautiful stop. There are a couple of lighthouses in the harbor worth visiting. Start at Owls Head Light, located in Owls Head State Park , dating to 1852. It’s a pleasant spot to spend an afternoon picnicking and exploring. On your way from Owls Head to the second lighthouse, stop by the Maine Lighthouse Museum to learn about maritime history and the lifesaving evolution of lighthouses along the coast.

The second lighthouse to check out is the Rockland Breakwater Lighthouse . Placed at the end of the breakwater to guide ships into the harbor, visitors can walk the entire length of the breakwater. Wear comfortable shoes, though, as the lighthouse is almost a mile out to sea.

Segment 2 Side Trip: Popham Beach

Only a 25-minute detour from the coastal route, Popham Beach State Park is a must-visit stop on the Boston to Bar Harbor road trip year-round. The ocean views are stunning, and the beach is amazing to explore; sand dollars and shells are common if you keep your eyes peeled.

If the tide is low, you can walk out to the largest of the Fox Islands, but beware of the changing tides. You don’t want to be stuck out away from the shore when the tide comes in and covers the path back to the coast.

Segment 2: Where to Stay

Along this segment, there are a plethora of campgrounds, especially around Freeport .

In Rockland, you can choose between a short-term rental, hotel, or even splurge on a bed and breakfast, such as the LimeRock Inn . Maine Forest Yurts is a fun choice, too.

Segment 3: Rockland to Bar Harbor

• Distance: 85 miles
• Drive time without stops: 2 hours

At last, you’re almost there! Much like the segment before, this stretch has plenty of quaint New England coastal towns to visit along the 85-mile stretch of road. Camden and Belfast are both great towns to explore. However, as you move north of Belfast, the route becomes a bit more remote and scenic.

There are still places to visit, but it’s as if the road knows that you don’t want any distractions on the way to your destination: Bar Harbor.

Segment 3 Highlight: Acadia National Park

Hardly a contest, the main attraction near Bar Harbor is Acadia National Park. From bathing on Sand Beach to hiking Cadillac Mountain to biking the extensive carriage trails network, Acadia itself is deserving of a weeklong trip.

Be sure to explore all of the best hikes in the park and hit up all the highlights along the Park Loop Road.

Related Read:   8 Spectacular Glamping Spots Near Acadia National Park, Maine

Segment 3 Highlight: Bar Harbor

Naturally, if you made it all the way here, you must take a bit of time to explore the hospitable town of Bar Harbor . Tuck into one of the small shops to find your souvenirs or head out to one of the many delicious restaurants — the Thirsty Whale has a great menu packed full of coastal favorites.

After some food, head out for a stroll along the Shore Path to take in sites of the harbor or out to Bar Beach. There’s also a trail (accessible only during low tide) that heads to the top of Bar Island.

Related read : T op 10 Campgrounds to Book for Your Visit to Acadia National Park

Segment 3 Highlight: Wildlife Cruises

The Bar Harbor Whale Watching Company offers all manner of on-the-water activities, from whale watching tours to a puffin and lighthouse cruise. Whale watching trips are between three and five hours, and after 30 years, the company has a good sense of where the whales will be, offering you the best opportunity to see the whales up close.

If you’re looking for a slightly shorter trip, the puffin and lighthouse cruises are an excellent opportunity to see all kinds of wildlife while touring the lighthouses. Make sure to bring your binoculars to see the wildlife in their full glory.

Segment 3 Highlight: Schooner Sail

If you’re into boating, set aside some time in Maine to sail on a schooner. The Downeast Windjammer Cruise Lines offers an assortment of opportunities, from morning sails to sunset cruises.

The evening sails can be romantic and fun as they serve wine and beer on board and often have live folk music on board for entertainment. The afternoon sail is a great option as it comes with a narration on local history and wildlife. The trips aren’t too much of a detour from Bar Harbor – the pier is about 15 minutes north of town.

Segment 3 Where to Stay

Bar Harbor is home to one of the country’s most popular national parks and you’ll have a huge assortment of lodging options.

Check out the beautiful airbnbs  nearby, stay at a yurt and wellness center or spring for the downright stunning Terramor Outdoor Resort . If you want to stay in Acadia National Park , though, you should make sure to book well in advance.

Explore More in New England

8 best beach camping spots in new england for an oceanfront getaway.

The 11 Best Things to Do in New England This Year

12 Magical Glamping Destinations in New England

5 Best Day Trips From Boston for Scenic New England Getaways

9 Best Airbnbs in Maine for a Unique New England Getaway

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Seen in: Maine , Massachusetts , New England , Northeast , Road Trips

Posted by Liz Dengler

Liz is a freelance writer and editor who lives on the road. Literally. Home is a cozy van parked wherever the views are stunning and the data is adequate. Always exploring, wherever she ends up, you can be sure she will be out hiking, biking, skiing, and paragliding.

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Boston to Portland, Maine: A Road Trip Itinerary (2023-2024)

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Are you looking for a fun and scenic road trip along the New England coast? If so, consider making the journey from Boston to Portland, Maine . It’s not a long road trip, but this scenic route takes you through charming coastal towns and offers plenty of opportunities for adventure, exploration, and fresh caught seafood, if that’s your jam!

To help you plan your Boston to Portland trip, we’ve put together a New England itinerary that highlights some of the best stops along the way. From Boston, Massachusetts to Portland, Maine, this coastal New England road trip offers a variety of suggestions for where to stop and what to do to make this a very memorable trip!

Table of Contents

How to Get from Boston MA to Portland ME

Do you know that you can easily take a train from Boston, Massachusetts to Portland, Maine?  The Amtrak Downeaster connects Boston and Portland, so if you’d like to skip the driving and just ride direct, that’s not a bad option at all. Amtrak trains can be a very convenient way to road trip, but you will of course miss out on all the fun stops along the way.

However, if you’re looking to get from Boston to Portland, Maine in just a couple of hours without having to slide behind the wheel of your car, you’ve got options. Check out the train schedule here . There are multiple Amtrak trains per day leaving from Boston North Station heading to Portland!

If you’d rather fly than ride, Logan Airport has plenty of flights from Boston to Portland, Maine, too! Jet Blue, American Airlines, Delta, and more fly daily between these two locations. Click here to look for deals on Boston to Portland ME flights !

If you’re the type of person who would prefer to control where you stop and for how long, drive. There is a direct route that takes you up I-95 that would get you from Boston to Portland ME in just under 2 hours, but that’s not for people looking for road trip adventures along the way.

Want the road trip experience but don’t have your own wheels? Click here to find deals on a rental car !

How Far is it from Boston to Portland, Maine?

Not very! Whether you’re traveling by plane, train, or automobile, it’s just about a couple of hours, but if you’re looking to enjoy some of the top sights in coastal Massachusetts and Maine, then it will take a couple of days at least to really get the full experience.

Can you do the drive in one day with quick stops at each spot? Technically, yes. But spreading this coastal road trip between Boston and Portland out over a weekend or longer will be more fun! 

We are including the best things to do at each stop between Boston and Portland and letting you decide where to spend your time during this very customizable coastal road trip.

We suggest allowing 2-3 days for this Boston to Portland ME trip, but you should personalize it any way you’d like. We’re even including our favorite places to stay along the way for overnight fun, too.

Where to Stop on the Drive from Boston to Portland, Maine

Stop 1: salem ma (20.2 miles via us-1n).

Kick off your trip by heading north from Boston to Salem, Massachusetts. Salem is a fascinating town with a rich history, and is worthy of being its own vacation destination, especially if you’re planning an October trip and looking for haunted places to visit and stay ! 

Salem is one of our favorite places to visit and it’s definitely worth a longer visit to take advantage of all the cool ghost and walking tours , but if you’ve only got a few hours to spend in Salem during your Boston to Portland road trip, these are our suggestions for what to see and where to stop:

• Hocus Pocus Filming Locations
• See the Salem Witch House
• Pay your respects at Salem Witch Memorial
• Grab a bite and/or a brew (coffee or beer!) at Gulu Gulu Cafe 

Where to Stay: Hotel Salem

Stop 2: Rockport MA (20.1 miles via MA-128 N)

Next up is Rockport, Massachusetts! Technically, this stop does take you just a bit off the relatively straight path north to Portland, but this charming coastal Massachusetts town is worth the detour, I promise. 

We have loved every visit we’ve made to this gem by the sea; it’s one of those quaint coastal places where you’ll find delicious restaurants, great breakfast spots , unique things to do, and even cool places to stay if you decide to do an overnight. These are our top recommendations for what to do in Rockport:

• Go strolling down and shop Bearskin Neck
• See Motif #1
• Enjoy a lobster roll at Roy Moore Lobster Co

Where to Stay: Emerson Inn

Stop 3: Hampton Beach in Hampton NH (36.9 miles via MA-133 W)

One of the most iconic beaches in New England , Hampton Beach is a definite must-visit if you’re taking a scenic road trip from Boston to Portland ME! In fact, it landed on Country Living’s list of the top eight “classic beach boardwalks” in the US, with the magazine citing the many offerings of Hampton Beach as being a perfect representation of classic summer nostalgia.

Of course, it’s true! Not only is there the beautiful beach with its picturesque boardwalk, but there’s also a lot of non beach fun nearby, like playing arcade games at Funarama, gambling a little at Ocean Gaming Casino, eating some yummy fried seafood, and then heading to Buc’s Lagoon Mini Golf and Ice Cream to play a round and follow up with a frozen treat!

Some must-dos while in Hampton Beach:

• Walk the Hampton Beach boardwalk
• Squish your toes in the soft sand at Hampton Beach State Park!
• Have some fun at Funarama

Where to Stay: Ashworth by the Sea

Stop 4: Portsmouth NH (13.6 miles via NH-1A N/Ocean Blvd)

Portsmouth is one of the top spots to visit on the New Hampshire Seacoast, and should not be missed on your road trip from Boston to Portland, Maine! Portsmouth has plenty of places to stretch your legs, with Strawbery Banke Museum, the historical outdoor museum, and the very walkable downtown with cobblestone streets and lots of great shopping- yay sales tax-free New Hampshire!

If you’re looking for a great place to grab a bite in Portsmouth, there are two notable spots to consider: Fezziwig’s Food & Fountain and Portsmouth Book & Bar . The former is a delightfully whimsical cafe that is perfect for a sandwich, pastries, and tea, and the latter is a bookstore/restaurant/bar that really delivers on all fronts! Both are memorable places to visit and eat in Portsmouth, but there are lots of cool breweries, bars , and breakfast spots to check out too!

Where to go on your Portsmouth stop:

• Enjoy living history at Strawberry Banke Museum
• Stroll pretty Prescott Park (you might even catch a summer concert!)
• Take advantage of no sales tax shopping!
• Grab a bite at Fezziwig’s

Where to Stay: The Hotel Portsmouth

Stop 5: York ME (10 miles via 95 N)

Once you’ve had your Portsmouth fun, head north to York, Maine. One of the coolest coastal towns in Maine, York is known for its beautiful beaches and historic sites and would be a fantastic stop on your Boston to Portland trip.

There’s plenty of great eye candy in York, with Long Sands Beach and Nubble Lighthouse; head to Sohier Park and you’ll have fantastic views of the lighthouse. For history lovers, the Old York Historical Society has impeccably maintained several historic structures, including the Old Gaol , originally built in 1656 as Maine’s first jail.

If you’re hungry in York, you’ve got options, but Fox’s Lobster House has been serving up fresh caught lobster and the finest blueberry pie since 1966, so they’re the place to go for a taste of quintessential coastal Maine!

These are some of the top things to do during your stop in York:

• Walk Long Sands Beach
• Ooh and ahh and photograph Nubble Lighthouse
• Visit the Old Gaol
• Eat at Fox’s Lobster House

Where to Stay: York Harbor Inn

Stop 6: Ogunquit ME (10 miles via US-1 N)

Next stop is Ogunquit, Maine, whose name means Beautiful Place by the Sea in the Algonquin language. This charming coastal town has lots to do and see , including scenic Marginal Way trail, which offers stunning views of the coastline, and lovely beaches that are perfect for sunbathing. 

Visit Perkins Cove, take a walk along the beach (Footbridge Beach is especially picturesque), or visit the Ogunquit Museum of American Art. The Ogunquit Playhouse has been a staple of this area since 1933, so if you can make the time, seeing a show at this iconic spot would be a memory-making activity, for sure. Pair this with a dinner at The Front Porch , the local piano bar/restaurant, and you’d be in for a great evening out in Ogunquit.

These are some of our top recommendations for your Ogunquit stop:

• Stroll Marginal Way
• Enjoy the scenery at Footbridge Beach
• Dine at The Front Porch
• Catch a show at the Ogunquit Playhouse

Where to Stay: Gorges Grant Hotel

Stop 7: Kennebunkport ME (11.7 miles via US-1 N and State Rte 9 E)

Onwards to charming Kennebunkport, Maine . This coastal Maine town is known for its historic homes, quaint shops, and beautiful beaches; a drive by the iconic Wedding Cake House (private property so keep a respectful distance) will confirm! 

Kennebunkport is full of great places to eat and shop, and heading to Dock Square will take you to many of them! This unique waterside area is home to several popular places to visit in Kennebunkport, and the Boathouse Restaurant is one of the most popular local restaurants that offer waterfront dining! 

What to do during your Kennebunkport stop:

• Drive by the Wedding Cake House
• Stroll and shop Dock Square
• Indulge a little at Boathouse Restaurant

Where to Stay: The Boathouse (yes, it’s also a lovely waterfront boutique hotel, too!)

Stop 8: Old Orchard Beach ME (18.2 miles via US-1 N to 95 N)

Next up is Old Orchard Beach, Maine, home to the last remaining beachfront amusement park in New England! Palace Playland has classic arcade games and amusement park rides, including a ferris wheel, roller coasters, and so much more, plus you’ve got beautiful Old Orchard Beach with its 7 miles of sandy beach to enjoy, too.

Another popular OOB attraction is the Old Orchard Beach Pier , home to all kinds of great places to eat, drink, shop, and enjoy that spectacular ocean scenery! Hungry? Grab a bite at Hooligan’s Steak & Ale, the first restaurant you’ll see when walking onto the OOB Pier! 

Must-do’s for your Old Orchard Beach stop:

• Play at Palace Playland
• Walk Old Orchard Beach
• Grab a bite at Hooligan’s on the Pier

Where to Stay: Alouette Beach Resort

Stop 9: Cape Elizabeth ME (17.1 miles via US-1 N)

The next stop on this Boston to Portland ME itinerary is Cape Elizabeth, home to some of the prettiest lighthouses in Maine . Granted, you’re just a few miles outside of Portland at this point, but skipping over a visit to the lighthouses in this lovely spot would be a travesty!

There’s Portland Head Light, the oldest remaining lighthouse in the state, Ram Island Ledge Lighthouse, and Two Lights, Cape Elizabeth Light and its twin, which is now a private residence. Cape Elizabeth is home to beautiful beaches, parks, and one of the best restaurants in Maine : The Lobster Shack at Two Lights.

Things to see in Cape Elizabeth:

• Tour Portland Head Light
• See Cape Elizabeth Light
• Eat at The Lobster Shack

Where to Stay in Cape Elizabeth: Inn by the Sea

Stop 10: Portland ME (8.5 miles via ME-77 N)

Finally, your destination is at hand! You’ve arrived in beautiful Portland, one of the top vacation destinations in Maine, and a town that seems to truly have something for just about everyone . You’ve got museums and art galleries, fun out on the water , shopping and browsing through Old Port, the Portland Observatory , and breweries, bakeries , breakfast spots , coffee shops, and restaurants galore to choose from.

In fact, if you’re a seafood lover, you’re going to LOVE the options you have for seafood in Portland! Check out Luke’s Lobster Shack on the Portland Pier for waterfront dining.

Portland has several great options for where to stay, including conveniently located vacation rentals and hotels , and beautiful boutique hotels that offer a variety of unique experiences, like the Press Hotel , located in the former headquarters of the Portland Press Herald. 

Whether you’re spending a weekend or a day in Portland, you’ll find fun in this popular Maine city by the sea.

What to do in Portland, Maine:

• Stroll Old Port
• Get out on the water
• Tour the Portland Observatory
• Eat some lobstah

Where to Stay in Portland: The Press Hotel

There are many different ways you can choose to get from Boston to Portland, Maine, but if you take the scenic route along the coast, you’ll have so many fantastic memory making opportunities! Coastal New England road trips are the best!

You might also like:

• Ultimate Boston to Acadia National Park Road Trip (2+ Day Itinerary)
• 5 Spectacular Maine Road Trip Routes You Won’t Want to Miss!
• New England Fall Road Trip: 8 Great Itineraries (+Bonus Ideas)
• The Ultimate Maine Coast Road Trip: Kittery to Bar Harbor

A Road Trip to Maine Itinerary You’ll Want to Steal

By: Author Girl with the Passport

Posted on Last updated: September 18, 2023

Categories North America

Planning a road trip to Maine? If so then THIS is the Maine road trip itinerary for you! After all, I’ve been to Maine countless times and want to share all of my amazing, expert advice with you.

In this way, I hope to make the entire trip planning process a whole hell of a lot easier for you. You know, so that you can actually enjoy your Maine road trip and not stress out about where to go, what to do, and how to get around.

Because believe it or not, Maine is easily one of the most beautiful states I’ve ever been to, which is why I’ve been countless times and definitely plan on returning ASAP – once I have the cash to do so.

So, if you love picturesque lighthouses, fresh steamed lobster, stunning coastal drives, and exquisite national parks, then a road trip to Maine will be the perfect trip for you.

However, enough chitty chat. You’re a busy human with tons of uber-important things to do. So, let’s swan dive into my beyond awesome expert tips that will help you plan just one of the many Maine road trips to come.

This post may contain affiliate links. Please see my disclosure for more information. As an Amazon Associate, I earn a small commission from qualifying purchases.

If you’re booking a trip right now then I IMPLORE you to get travel insurance – even if it’s not from me. 

After all, this past year has been a wild ride and I don’t want you to lose money because government regulations have changed. 

Truth be told though, I’ve never traveled without travel insurance and don’t think you should either – especially since I think we’ve all had plans drastically change because of the pandemic. 

Therefore, find an insurance agency that covers travel changes related to COVID-19, like my two all-time faves World Nomads and Safety Wing . You can also read more about which policy is right for you in my full review here .

🕒 In a hurry and haven’t planned your road trip to Maine yet? Book this self guided driving tour of Acadia National Park and Bar Harbor . It is a fun way to explore the area on your own! ⛰️

How To Get To Maine For Your Road Trip To Maine

Since I live in New York, I normally just drive to Maine. However, if you’re from out of town and want to fly into Maine, then you could always fly into Portland International Jetport.

It’s pretty convenient since it’s only about two miles from downtown Portland and services flights from all over the world. Upon arrival, I’d absolutely rent a car since you obviously can’t do a road trip to Maine without one!

However, if you want to visit Portland for a few days and then rent a car, you could always take the route #5 bus to downtown Portland and then rent a car once you’ve experienced some of the fun things to do in Portland .

Pro Tip: You could also try flying into Boston Logan International Airport. It’s way bigger than Portland and is a major travel hub both internationally and domestically.

Therefore, you could probably find a cheap flight to Boston and then just drive to Maine from there since it’s only about an hour and a half drive from there to the Maine border.

But, if you’re not really interested in flying, you could always try:

Amtrak trains from all over the US travel directly to multiple train stations throughout Maine. So, this is definitely an option if you don’t really feel like flying. Just do your research first since train travel in the US can be really expensive.

I mean, a one-way, coach ticket from Newark to Portland starts at $63 per person and takes 9.5 hours. So, you could definitely end spending more money on a train ticket than on a flight.

Two different bus companies operate throughout Maine and have routes that go into and out of the state. Of the two, Concord Coach Lines is more local with routes from Maine that stop in major cities in New York, Massachusetts, and New Hampshire.

Tickets start as low as $79.00 one way and $158.00 round trip. In contrast, Greyhound runs buses into and out of Maine from most major cities across the country, with one-way tickets from Boston to Portland starting at as little as $16 per person.

How To Get Around During Your Road Trip To Maine

Since you’re planning a Maine road trip, you’ll obviously need a car while you’re here. Luckily for you, Portland International Jetport is pretty small. Therefore, it will be really easy for you to get to Hertz, Alamo, Avis, Dollar, Enterprise, or Budget Car Rental to actually rent a car before you start your Maine road trip itinerary.

Yeah, they have a fleet of more than 200 cars that are all located inside the consolidated car rental atrium that is protected from the elements (i.e. rain and snow) inside the airport’s new parking garage. It’s also literally steps away from the terminal so you’ll have zero problems finding a car rental.

When choosing a car though, you’ll want to make sure that it gets good gas mileage and that the interior is super roomy. This way, you can relax and be supremely comfy during your road trip to Maine.

Now, in terms of cost, you should on average expect to pay $409 to rent a car for a week and $149 to rent a car for the weekend. Anything significantly more expensive than this is probably not something you need to invest in.

When To See Fall Foliage in Maine

Since my family and I would routinely visit Maine every October throughout my childhood, I know all too well that many people like to road trip to Maine to see fall foliage.

So, if you want to see fall foliage while you’re here, the best time to visit Maine is between late September and mid-October (Columbus Day Weekend is the perfect time to visit and is when my family used to go).

Generally speaking, this is when fall foliage is at its most stunning. Although this time frame can vary by elevation and latitude since some high-elevation, more northern areas across Maine enjoy peak fall foliage in late September.

And if you want even more expert advice on visiting Maine this fall, then check out my ultimate guide to fall in Maine now!

The Ultimate Road Trip to Maine Itinerary

1. ogunquit.

More likely than not, when you start your Maine road trip itinerary, you’ll probably be near the state’s southernmost point. So let’s start our road trip to Maine there!

And what better place to begin the best road trip in Maine than in a place whose name literally means “beautiful place by the sea” in Native American, Abenaki?

Plus, plenty of people seem to agree with this description since Ogunquit is easily one of the most popular summer tourist destinations in all of Maine.

Which makes sense since the beach here is stunning, the sea air is refreshing, the cocktails are delicious … I’m seriously thinking about moving there permanently right now!

That’s why, Ogunquit is definitely one of the best beach towns in Maine , and now you too will get a chance to experience the awesomeness for yourself!

Because while you’re here, you can see a show at Ogunquit Playhouse, walk along the scenic Marginal Way walking path (it’s only around 1,25 miles long), or visit the quaint fishing village of Perkins Cove.

Other Things To Do In Ogunquit

Ogunquit museum of american art.

If local art is what floats your boat (nautical pun intended!) then the Ogunquit Museum of American Art is the place for you! There are over 3000 individual pieces of art on display throughout this museum. And honestly, I’m not all that surprised, seeing as they first opened in 1953!

Paintings, sculptures, and photographs aplenty are all permanently on display in this deliberately American-focused museum.

Before you leave, be sure to explore their 3-acre sculpture park, complete with 18 small gardens that will delight your eyes and help you relax as you take in all the culture and artistry. A walk in the park that makes you feel smart and creative? Sign me up!

Take A Scenic Cruise Along The Coast

The sea looks great, but Ogunquit looks even better from the water!

So, hop onto a boat and treat yourself to a tour of the coast: learn about the history of the town, see the historic lighthouses which make this great American state so famous, and find out something new about the world of lobsters and lobster fishing. It’s a Maine tradition!

Because whether you’re sipping cocktails on a luxury yacht, or enjoying the simpler life by gently sailing by on a rustic wooden sailboat, a scenic cruise will make your visit to Ogunquit and your super awesome Maine road trip complete!

What To Eat In Ogunquit

Barnacle billy’s.

It’s time to grab some of that famous Maine lobster during your road trip to Maine! And Barnacle Billy’s is the place to do that since it’s famed for its luxurious lobster dishes – in addition to plenty of other fresh fish dishes too – that you can order along with a delicious bowl of clam chowder.  

So, whether you decide to dine indoors or out on the sundeck, the stunning ocean views will be the perfect accompaniment to your meal!

Wait, am I eating a ray gun? Nope! This is place serves delicious urban Thai food. So, put some kick into your food by ordering some of their spicy and exotic dishes!  

And although they do have Thai staples like green curry and fried rice, do try some of their house specials, especially the crispy duck with orange sauce. There are also plenty of vegan and gluten-free dishes here too!

Where To Stay In Ogunquit

The grand hotel (ogunquit).

⭐️ Rating: 8.9/10 (581 Reviews) Price: $101 per night 📍Location: 276 Shore Road, Ogunquit, ME Details: Read more on booking.com now!

If you want to live the high-life for a hot minute then the Grand Hotel will help you to relax in style! Because on top of having a spacious room with a private balcony, you’ll also enjoy access to an indoor heated pool and an outdoor jacuzzi for maximum pampering!

“Location was perfect, room was spacious and clean! One of the nicest rooms I’ve ever stayed in. Entire property was super clean. Price was very reasonable. Small balcony with chairs off the bedroom, wish I would have had more time to enjoy them. Will definitely stay here when I return to Ogunquit! Well done!!” Kim ( read more reviews now! )

There’s also plenty of deck space here for an evening drink outside at this well-located hotel, which sits less than a mile away from the Ogunquit Museum of Modern Art!

Wells Moody Motel (Wells)

⭐️ Rating: 8.6/10 (626 Reviews) Price: $89 per night 📍Location: 119 Post Road, Wells, ME Details: Read more on booking.com now!

Just up the highway from Ogunquit, the Wells Moody Motel offers guests all the friendly and exceptional service you could hope to receive during a Maine road trip.

“We were greeted in the office very warmly. check in was easy. First impression of the Motel was it was very cute. property was well taken care of. We pulled around to our room there was a cute little porch in front. went into the room and it was very clean! T he bed and pillows very comfortable. The bathroom was very clean. The 2 rooms we were in looked like they had maybe been recently updated. very pleased with our stay.” Michelle ( read more reviews now! )

They offer bright and well-equipped rooms that will make you feel right at home. The beds here are also super comfy, and include access to an on-site, outdoor pool!

2. Kennebunkport

It’s time to head further north to iconic Kennebunkport – at least if you to make this Maine Road Trip truly epic. Because if you want beaches, Kennebunkport has got em’! So, be sure to give both Goose Rocks Beach and Arundel Beach a try!

And you know people love them since this coastal town has been offering visitors professional levels of hospitality since the 1800s. So, they’re obviously pretty dang good at it by now!

Because with stunning sea views, sandy summer beaches, historic churches (St. Anne’s Episcopal Church dates all the way back to 1887 and features stunning architecture), and beautiful fall foliage, Kennebunkport is truly one of the best romantic getaways in Maine .

It’s even magical when it’s covered in snow! That’s why there’s really no time of year when this place doesn’t look like it belongs on a postcard!

Things To Do In Kennebunkport:

Visit the goat island lighthouse.

If you head over to Cape Porpoise, you’ll find this nearly two-hundred-year-old landmark of New England standing proudly by the shore on its own little island.

Legend has it that this ancient watchtower used to be a lookout point for Secret Service agents of George H.W. Bush, WAY back in ye olde 1993. I know, that’s not that long ago. But it’s still history, y’all!

Check Out The Seashore Trolley Museum

This is one of my favorite things to do in Kennebunkport Maine ! There are over 250 antique streetcars, buses, and other vehicles all collected together in one place. And they don’t all just sit there either!

Because every 45 minutes you can board one of these vintage trolleys, take a ride around the museum, and experience what it really felt like to travel in the early 1900s!

What To Eat In Kennebunkport

Alisson’s restaurant.

When planning a road trip to Maine, food is of the utmost importance. And thankfully, you can get almost anything you want, at Alisson’s Restaurant!

There’s a huge amount of generously portioned pub food available, including lobster mac ’n’ cheese, steak and shrimp salad, mussels, clams, tacos, pizzas, sandwiches, and of course, blueberry pie!

And since Alisson’s is also a pub, there’s a large selection of cocktails, wines, tequilas, and whiskeys to help you party the night away!

Rococo Artisan Ice Cream

Time to satisfy that sweet tooth! And in addition to all the crowd-pleasing, traditional flavors, Rococo also specializes in creating unique – yet tasty – varieties of ice cream.

I mean, have you ever had Goat Cheese ice cream? How about Garam Masala? Or Banana Red Hot? Now’s the time to try them out and be adventurous!

Where To Stay In Kennebunkport

The breakwater inn and spa (kennebunkport).

⭐️ Rating: 7.2/10 (21 Reviews) Price: $199 per night 📍Location: 127-133 Ocean Avenue PO Box 560C, Kennebunkport, ME Details: Read more on booking.com now!

This historic Victorian-era property is a charming Maine guest house. It has all the trappings of a comfortable night’s rest, with the added bonus of a spa, a fitness center, free wi-fi (obvs), continental breakfast, and bike rentals for getting your fitness on while you sight-see!

The in-house restaurant also provides guests with great views of the ocean, which goes well with the Breakwater Inn’s nautical theme!

The Lodge at Turbat’s Creek  (Kennebunkport)

⭐️ Rating: 8.9/10 (176 Reviews) Price: $199 per night 📍Location: 7 Turbat’s Creek Road, Kennebunkport, ME Details: Read more on booking.com now!

The Lodge at Turbat’s Creek is well situated, friendly, and extremely comfortable. The furnishings are also high quality, the breakfast is very generous, and you can meet other travelers out in the garden, pool, and restaurant areas. Perfect for a well-deserved pit stop during your road trip to Maine!

3. Portland

Portland is easily one of my favorite places to visit in Maine. So much so that I’ve been there at least 15 different times!

Because this hipster paradise has it all: the cobblestone streets of the Old Port area, the historic beauty of Victorian mansions, the amazing art of the Portland Museum of Art, the inventiveness of craft beer breweries, and even its very own observatory for all y’all science geeks!

But, one of the best things about Portland is that while it is a city, it still has tons of green spaces and expansive natural areas that allow you to enjoy all the natural beauty of Maine. Yup, it really is the best of both worlds!

I mean, you can easily go from vibrant nightlife and culture to strolling along the Eastern Promenade, breathing in the sea air. You could also take scenic photos at nearby Bug Light or walk along the breakwater to ever awesome Spring Point Ledge Light (it’s tucked away inside a college campus).

Or, you could head over to Cape Elizabeth and do a bit of lighthouse spotting! Wait, Kelly, is that a sport? Well, it is now since Maine is famous for its lighthouses, with over 150 lining the Northeast, with plenty of them being in Portland.

Pro Tip: While you’re in Portland, definitely do a day trip to Cape Elizabeth. There are a ton of great parks here and this is also where you can see Portland Head Light and Cape Elizabeth Light!

If you want, you can even check out my list of the best lighthouses in Portland Maine if you’re interested!

Things To Do In Portland

Visit the victoria mansion museum.

Fancy a blast from the past? This 1860s Italianate palace is one of the best historic homes to visit in Portland Maine. The elaborate frescoes, the intricately detailed carpets, and the period-piece furniture will have you falling in love with the good ol’ days.

See, you don’t really need a time machine to find out just how lush and OTT they used to have it back in the day – just come and see Victoria Mansion!

Take The Ferry Out To Peaks Island And Rent A bike

If you’re looking for cute streets and lush wilderness in which to ride around and feel the wind in your hair, just hop onto the big yellow Casco Bay Lines ferry and take the 20-minute trip out to Peaks Island. Here you can rent a bike (or a golf cart if you’d prefer not to have to do too much peddling) and take in the many MANY gorgeous views of the ocean!

What To Eat In Portland

Duckfat friteshack.

You heard me! If you want the crispiest, tastiest, LARGEST portion of fries in the state of Maine, make sure you stop by the Duckfat Friteshack.

These hand-cut fries can be a quick snack or their own full meal, depending on your appetite. Each portion comes with your choice of two of the Friteshack’s dips – truffle ketchup is my personal fave!

The Holy Donut

Ok, so following this Maine road trip itinerary may not be the healthiest choice for your figure, but we’re here to have fun, y’all!

And eating at The Holy Donut is one of the best things to do in Portland Maine, period! These donuts are big enough to share (if you’re feeling generous), so tuck into a sea salt and chocolate donut (highly recommended) as fast as you can!

Where To Stay In Portland

Inn at st john portland (in-town, portland).

⭐️ Rating: 8.4/10 (989 Reviews) Price: $149 per night 📍Location: 939 Congress Street, Portland, ME Details: Read more on booking.com now!

Located right in the heart of Portland and never too far from anything you could want to see, this cozy and colorful inn will leave you feeling fresh and ready for a fun day of sightseeing. The Inn at St John Portland In-Town is also pet-friendly, so feel free to bring your furry friends along for the ride!

Portland Harbor Hotel (Portland)

⭐️ Rating: 8.5/10 (766 Reviews) Price: $179 per night 📍Location: 468 Fore Street, Portland, ME Details: Read more on booking.com now!

With a restaurant, fitness center, free bike use, flat-screen TVs, and wi-fi all conveniently tucked away inside the Old Port district, this hotel ticks off a lot of boxes! And for those looking for a splash of luxury during their Maine road trip itinerary, this is definitely of the best places to stay in Portland Maine!

4. Waldoboro

Waldoboro is one of those towns that you will definitely drive through during your road trip to Maine. It is known for its three lakes and has a rich and thriving fishing and agricultural history. 

Take your pick of Duckpuddle Pond to Damariscotta Lake or Pemaquid Pond and spend a relaxing summer day swimming, fishing, or watching a gorgeous sunset. 

For more outdoor fun hit the trails at the Goose River Peace Corps Preserve and Pond. Or take refuge from the elements and head over to the Waldoboro Historical Society and learn more about this quaint New England town.

Things to do in Waldoboro

Visit fawcett’s antique toy museum.

This quirky museum is right on Atlantic Highway and it is worth a stop if you are just driving through town. Every surface is covered with memorabilia as far back as the 1920s and 1930s. 

Owl’s Head Transportation Museum

Even though Waldoboro is known for its lakes, this museum isn’t focused on boats but on other types of transportation. On display are antique cars, trains, and motorcycles. 

What To Eat In Waldoboro

Moody’s diner.

You can’t miss Moody’s Diner if you are on Route 1 driving through Waldoboro during your road trip to Maine. It is a family-owned restaurant that has been serving the local community since 1927. Classic diner fare is on the menu but watch out for the blueberry pie or whoopie pies for an extra special Maine treat. 

Odd Alewives Farm and Brewery

Just behind Moody’s is the Odd Alewives Farm and Brewery. Odd Alewives uses ingredients from their own land and other local farms. There is plenty of seating on the premises and they even have a fire pit to roast marshmallows and make smores. Their beer is also great to pair with pizza that they also make on-site in a brick oven.  

Where To Stay In Waldoboro

Friendship harbor historic home (friendship).

⭐️ Rating: 8.3/10 (3 Reviews) Price: $236 per night 📍Location: Waldoboro, ME Details: Read more on booking.com now!

This Victorian Harbor House is right on the water and has its own dock. Literally, in 15 seconds you’ll be in the water! It may be from the 1800s but it is newly renovated with modern amenities plus it is near enough to town but still quiet.

The owners live nearby and their sons can drop off lobster that they catch themselves. Without a doubt you’ll get the full Maine experience! 

Damariscotta Lakefront Retreat (Newcastle)

⭐️ Rating: 5/5 (18 Reviews) Price: $636 per night 📍Location: Nobleboro, Maine, United States of America Details: Read more on Vrbo!

If you are craving a quiet retreat away while on your road trip in Maine, this cabin is just the ticket. It is steps away from Damariscotta Lake where you can go swimming or you can spend your days relaxing on the deck and doing nothing. Hey, it’s your vacation and you can do you! 

5. Rockland

Just a couple of hours further up the highway from its half-namesake on the mid-coast of Maine, Rockland has all the charm of many other New England coastal towns.

But, it’s much less busy than Portland -and other more southern towns – since it’s a bit further away from Boston. In fact, if you’re planning a road trip to Maine during the off-season, that’ll be the perfect time to visit this jewel of the east coast!

See, Rockland’s local economy moved away from fishing in the 1990s, and began to focus more on catering to the increasing amounts of tourists coming to stay.

As a result, the downtown area is now full of boutiques, cute little restaurants, museums, and other assorted historical buildings. No wonder their nickname is Vacationland!

And some of the best things to do in Rockland include a stop at the Support Puffin Project Outpost in town, a visit to the Maine Center for Contemporary Art, a quiet walk along the Rockland Harbor Trail, a visit to the historic Olson House, and a cruise aboard a vintage Windjammer.

Things To Do In Rockland

Visit the farnsworth art museum.

Good news everyone! Rockland has its very own regional art museum, and it’s pretty dang good!

In total, there are 15,000 different paintings, sculptures, and other works of art collected here, with several exhibitions going on continuously throughout the year, covering everything from local artistic contributors to world-famous American artists.

Come and see what they’ve got for yourself – there’s even a cute little library!

Walk Along The Breakwater to Rockland Breakwater Lighthouse

Not only is this activity totally free, but the walk is wonderfully scenic and culminates in a stop at an enchanting lighthouse from 1902. Just be careful since the breakwater is extremely uneven.

However, if you visit during the summer, you’ll be able to explore the interior of the lighthouse after walking 7/8th of a mile out there!

What To Eat In Rockland

Archer’s on the pier.

For the best in locally owned and locally prepared Rockland food, Archer’s on the Pier is your Maine (get it?) port of call! There’s all the usual amazing seafood options – lobster for days, yo! – as well as steaks, burgers, sandwiches, and pasta. Depending on when you dine, you might even get treated to some live local jazz music!

Cafe Miranda

It’s chowdah time people! Fresh, creamy, delicious seafood chowdah, and lots of it! The portion sizes here are also HUGE, so come hungry! Whether you go for the chowder, or would rather have a hotdog, a sammie, or a salad, prepare to feel full when you leave!

Trust me, enjoying a meal at Cafe Miranda with its quirky array of pink flamingos (I’m not even joking) is one of my fave things to do here.

Where To Stay In Rockland

The craignair inn by the sea (spruce head).

⭐️ Rating: 9.4/10 (26 Reviews) Price: $164 per night 📍Location: 5 Third Street, Spruce Head, ME Details: Read more on booking.com now!

At the end of a long dead-end road lies a beacon of rest and relaxation. Just south of Rockland, the Craignair Inn by the Sea is like something out of a storybook.

Seriously, picturesque doesn’t even cover it! The owners are also super friendly and accommodating, the beds are soft and warm, and the rooms are well equipped and spacious. Get yourself here now!

Trade Winds Inn (Rockland)

⭐️ Rating: 7.7/10 (647 Reviews) Price: $107 per night 📍Location: 2 Park Drive, Rockland, ME Details: Read more on booking.com now!

To truly get a taste of coastal Maine, make sure you try out this boardwalk-style hotel. It sits right on the banks of Rockland Harbor and has just the right balance of antique and modern facilities. The bar area is casual and comfy while the indoor pool and fitness center are both first class. Need I say more?

Up, up, up the coast we go! Because Camden is our next stop on this Maine road trip itinerary. And residents of Camden love to be “where the mountains meet the sea”, and I am here to tell you that that is accurate!

After all, Camden lies right at the foot of Camden Hills State Park, meaning visitors can enjoy the vibrance of the harbor town community while still being able to escape into the sprawling wilderness of natural New England.

So, whether you want to exercise your body or your mind – or your tastebuds – Camden will have something for you!

Pro Tip : If you’re short on time when planning your road trip to Maine (and who isn’t) you can combine a trip to Camden with a stay in Rockland.

I mean, Camden is only about twenty minutes down the road from Rockland so you could EASILY do a day trip here. I also personally preferred Rockland to Camden but, hey, that’s just me.

Things To Do In Camden

Camden hills state park.

As I said before, Camden is right next door to this State Park. And with 30 miles of hiking, biking – and in the winter months, skiing – trails available, you can lose yourself for hours in this lush oasis of greenery.

And if you’re feeling truly adventurous, you can hike up to the top of the 1,384 foot tall Mount Megunticook, for some of the best views of Penobscot Bay as you conquer one of the best hikes in Maine !

Picnic at Megunticook Lake

Pack up your picnic basket and travel just a few miles north of Camden Harbor to find this highly Instagrammable slice of the quiet life! Because Megunticook Lake has tons of designated picnic areas for you to use that come complete with grills and tables.

Plus, if you fancy a swim, the lake itself has a floating diving platform for you to use, as well as a shallow area for younger swimmers!

What To Eat In Camden

Fresh & Co – This family-owned local business is the place to go for fresh, down-to-earth meals. Fresh & Co primarily focuses on sustainability, with extra care given to the ingredients and the flavors of their dishes. They also showcase local artwork on their walls. It’s truly a deep dive into Camden local life!

40 Paper – French, Spanish, Italian, and Mediterranean influences all come together in this former mill from the civil war! But don’t worry: while the dishes may be very European, the ingredients are all fresh from Maine since 40 Paper works with local farmers and fishermen to bring you the best of the catch!

Where To Stay In Camden

Cedar crest inn (camden).

If you’re looking for great service and great value, Cedar Crest Inn will provide! Located just to the south of downtown Camden, this seasonal motel has an outdoor pool, on-site restaurant, and comfortable rooms.

There’s also an outdoor play area for those traveling with young children!

Elms of Camden (Camden)

⭐️ Rating: 9.3/10 (63 Reviews) Price: $186 per night 📍Location: 84 Elm Street, Camden, ME Details: Read more on booking.com now!

Elms of Camden features cozy and luxurious rooms that all come with a complimentary, multi-course breakfast that is served to you fresh, every single morning. Why yes, I will take another helping of pancakes, thanks for asking!

“Gary and James are gracious, thoughtful hosts, taking pride in their commitance. they obviously love it and so do their” Nicholla ( read more reviews now! )

The hosts here are also all about hospitality, and will work extra hard to make sure your Maine road trip is the best ever!

7. Acadia National Park

Meet Acadia National Park. It is the only national park in all of New England but comes fully outfitted with 47,000 acres of land. 158 miles of hiking trails. 1,100 different species of plants, and over 400 different species of animals. Oh, and a casual 20 mountains for you to climb.

Like the notorious Cadillac Mountain, which is the perfect place to go to see the very first sunrise in the United States. However, if you don’t feel like climbing all the way to the top, you can always drive up and just do the easy, 0.5-mile loop trail around the summit.

Not surprisingly, Acadia is easily one of the top 10 most visited national parks in the United States and it’s one of the last stops on our road trip to Maine!

And what a stop it is. Once you cross the bridge onto Mount Desert Island, you’ll feel like you’re really getting back to nature as you head towards the forests, lakes and hills of Acadia National Park. So, stretch your legs and enjoy all that this amazing stop on your Maine road trip itinerary has to offer!

Things to do in Acadia National Park

I do believe i mentioned the hiking trails….

As with many State Parks, Acadia National Park has hiking trails for all levels of expertise and challenge. Beginners and casual walkers can enjoy the Jordan Pond Nature Trail, or see panoramic views on the Cadillac Summit path.

For a good afternoon hike though, visitors can try the Ship Harbor Nature Trail, or head over to Bar Island to explore its beautiful forests (though only at low tide – make sure you keep your eye on the time or you’ll be trapped)!

And If you’re feeling more adventurous, the Great Head Trail will take you out to the Sea Cliffs on the east side of Sand Beach. Otherwise, if “hiking” is basically your unofficial middle name, then Precipice Trail awaits you!

It’s one of the best hikes in Acadia National Park and features small obstacles like an almost vertical 1,000-foot climb at one point. Erm, if you need me, I’ll be in the bar ….

Take A Horse-Drawn Carriage Ride

Sure, you could hike. Or would you rather have the gorgeous natural scenery roll gently by you as you pretend to be Queen of All you Survey in your very own horse-drawn carriage? Yeah, I’d opt for the latter too.

So, If you feel like I do, then make your way down to Wildwood Stables on the southeast side of the island and you can do exactly that! Daily carriage tours are provided here from May through October and follow along roads originally constructed by John D. Rockefeller in the early to mid-1900s!

And if you really want to have the Maine road trip of a lifetime and you lead an enviable lifestyle, you can bring your own horses with you and ride with them instead!

What to eat in Acadia National Park

Do you ever wish for the purrr-fect breakfast? Well, that’s what you’ll find at 2 Cats in Bar Harbor! Their creative homemade breakfast combinations feature everything from pancakes and bagels to tofu scramble and granola.

Plus, you’ll get baked biscuits and strawberry butter with pretty much every order! Yup, now that’s what I call a Maine road trip winner.

Jordan Pond House Restaurant

Believe it or not, there’s actually a restaurant INSIDE Acadia National Park. It overlooks Jordan Pond and is great place to go for some pop-overs, chowdah, and a fresh Maine lobstah roll.

Where To Stay In Acadia National Park

Acadia inn (bar harbor).

⭐️ Rating: 8.7/10 (1090 Reviews) Price: $134 per night 📍Location: 98 Eden Street, Bar Harbor, ME Details: Read more on booking.com now!

This stylish and well-maintained hotel comes with an outdoor pool – complete with hot tub – a complimentary breakfast buffet, flat-screen TVs, and wi-fi.

“Excellent location about a mile from downtown Bar Harbor. It’s an easy walk to town, so you don’t need to drive and stress about parking. Also very close to Acadia and all the top attractions. Bed was very comfortable and the room was clean, good water pressure in the shower, convenient grab and go breakfast, and a hot tub to top it off. I’d definitely stay here again.” Justin ( read more reviews now! )

But most importantly, it lies connected to a trail that leads directly into Acadia National Park itself! Just grab yourself a good night’s sleep, fill up on their tasty breakfast, step out the door, and start walking. It’s that simple!

Bar Harbor Grand Hotel (Bar Harbor)

⭐️ Rating: 9.1/10 (631 Reviews) Price: $189 per night 📍Location: 269 Main Street, Bar Harbor, ME Details: Read more on booking.com now!

With its location right in the center of downtown Bar Harbor, you’ll be well connected to both Acadia National Park and Bar Harbor’s sprawling coastal beaches.

But, you might be tempted to just stay indoors since the rooms here are super comfortable and well furnished, with modern fixtures amongst period decor.

“Location is great . Furniture and setting is so nice . Parking is comfortable and large of space.” Gerardo ( read more reviews now! )

Heck, there’s even an indoor pool and fitness center just in case you want to get your fitness-related swerve on. It’s honestly one of the more luxurious places to stay during your road trip to Maine!

8. Bar Harbor

This not-so-secret coastal town is a not-so-secret stop on our Maine road trip itinerary. And that’s basically because Bar Harbor is known as the gateway to everybody’s favorite…Acadia National Park.

So, if you’re short on time, You could always do a day trip and experience all that Bar Harbor has to offer as part of your trip to Acadia.

Because honestly, there really is a ton to do in this picturesque coastal town, besides visiting nearby Acadia National Park of course. I mean, if you’re at least a semi-morning person, you could get up before dawn and walk the length of the beautiful Shore Path.

It was originally built in 1880, is about a 1/2 mile long, starts at the town pier and Agamont Park, and offers you stunning views of the surrounding, Porcupine Islands.

Afterward, explore the Wild Gardens of Acadia, which are truly stunning to behold and home to over 200+ incredible plant species. Next, check out the Abbe Museum, which is a full on, Smithsonian institution that educated visitors about Native American history and culture in Maine.

And if that’s still not enough fun stuff for you to do during your road trip to Maine, then you could always visit other local attrations like the George B. Dorr Museum of Natural History, the College of the Atlantic Gardens, and the Mount Desert Oceanarium.

Pro Tip: Wanna get out of the country and explore Canada? If so then hop aboard the high-speed CAT Ferry and take it all the way to Canada! The journey lasts about 3.5 hours and will drop you off in Yarmouth, Nova Scotia.

Once here, you can enjoy the beauty of Cape Breton Highlands National Park, visit the Maritime Museum of the Atlantic, and admire the Halifax Public Gardens of the Halifax Citadel National Site,

What to Eat in Bar Harbor

Ben and bill’s chocolate emporium.

Fudge? Check. Ice cream? Check. Candies? Oh yeah! Plus, pretty much everything on offer here is homemade and guaranteed to send your tastebuds spinning. And, FYI, I mean that in the best possible way.  

And with over 70 different flavors of ice cream and gelato available, you’ll feel like a kid in a … well, you know what I mean!

The Barnacle

Stuff your face silly at this amazing Bar Harbor restaurant, which is known for its delicious cocktails. Personally, though, I love their oysters and their next-level awesome pesto pasta.

CIAO Food/Drink

This place is equal parts popular and small. So yeah, you’ll probably have to wait to get inside. But once you’re across the threshold, your patience will be rewarded with delicious French lobster rolls, pork belly tacos, and fried cauliflower.

The portions are also on the small-ish side so definitely order a few things.

Where to Stay in Bar Harbor (see above for more recs)

The inn on mount desert (bar harbor).

⭐️ Rating: 9.3/10 (913 Reviews) Price: $199 per night 📍Location: 68 Mt. Dessert Street, Bar Harbor, ME Details: Read more on booking.com now!

This charming family-owned inn has a modern but relaxed feel about it that everyone will love. Rooms here are also well-priced at around $150 per night and include free Wi-Fi, flat-screen TVs, tea/coffee-making facilities, minifridges, and more.

“Had the feel of a BnB much more than a hotel. Delicious homemade breakfast including omelets to order as well as homemade muffins and bread. EXTREMELY CLEAN. Short drive to Acadia Natl Park!” Macayla ( read more reviews now! )

As a guest, you’ll also enjoy a delicious, daily breakfast as well as access to a private balcony with harbor or garden views.

Full disclosure, this is a supremely quiet, extremely tiny town along the Northern coast of Maine. So yes, this stop on your road trip to Maine will be pretty chill and mainly for people who love the great outdoors.

But it’s a wonderful, sleepy little fishing village that was first founded in 1826 along the Machias.

Today though, you can make your way through one of the area’s many awe-inspiring hiking trails, including Bog Brook Cove, Cutler Bold Coast Trail (it’s an amazing hidden gem that you shouldn’t miss), and the trails within the Western Head Preserve.

However, because you’re so far North, you could easily cross the border into Canada and check out the Bay of Fundy since the border with Canada is only about an hour and fifteen minutes away. If you want to drive all the way to Nova Scotia though, it’ll be about a 6-hour drive, so be prepared.

Things to do in Cutler

Hike or bike on through the cutler coast public reserved land.

This 12,334-acre wilderness area is brimming over with expansive blueberry barrens, pristine woodlands, and peatlands that feature jaw-droppingly beautiful cliffside views of the Bay of Fundy. There are also a ton of remote campsites here where you can really channel your inner Bear Grylls if you so desire.

Little River Lighthouse

Take a scenic walk to this quaint AF lighthouse, do a guided tour of the facility to learn about its fascinating history, and – if you’re lucky – spend the night for a truly memorable stay in Cutler.

Go On A Cruise With The Bold Coast Charter Company

Go on an amazing boat ride to Machias Seal Island. While you’re here, you can marvel at the single biggest puffin colony in all of Maine.

What to Eat/Where to Stay in Cutler (there are a distinct lack of options here)

For food, you can enjoy some delicious local fare at Heen’s Restaurant. Otherwise, you can venture into either Jonesboro and Machias for a wider selection of good eats.

The Bluebird Motel (East Machias)

⭐️ Rating: 8.4/10 (252 Reviews) Price: $99 per night 📍Location: 231 Dublin Street, Machias, ME Details: Read more on booking.com now!

Yeah, there aren’t a ton of places to spend the night in Cutler. However, the rooms at the Bluebird Motel are well-priced (less than $100 per night) and consistently given great reviews by guests since they have everything you need for a comfy stay.

10. Rangeley Lake (An Inland Stop For Anyone With A Bit Of Extra Time)

If you have an extra day or two to spare, then here’s another great spot to add to your Maine road trip itinerary! It’s located in western Maine, a mere 40 miles from the New Hampshire border.

Because the Rangeley Lakes region is a picturesque, expansive area that is filled with stunning natural beauty. It also includes a grand total of six different lakes, like Rangeley Lake itself.

This idyllic rural destination also has a large number of green spaces and waterways for visitors to enjoy, perfect for spending time getting back into nature, and enjoying all the comforts that a small-town vacation can bring.

And if you’re a fan of seaplanes, then you’re in luck because Rangeley Lake is a designated water landing zone for seaplanes. Therefore, you might find yourself watching one of these bad boys speeding down and coming to a steady stop on the surface of the water!

Things To Do In Rangeley Lake

Rangeley lake state park.

Almost 90 acres of land makes up this state park. It also sits on a section of the Appalachian Trail that runs along Saddleback Mountain and is a popular place to rent a kayak and get yourself out onto that crystal clear water!

However, If you’re more of a landlubber like me, then there are plenty of trails for hiking, camping, and picnicking areas, as well as spots for viewing tons of amazing wildlife. There are also plenty of opportunities for fishing since the waters here are full of trout and salmon.

Rangeley Outdoor Sporting Heritage Museum

If you’re more of a city person, and the idea of actually catching a fish yourself sounds like a total nightmare, then you can always just learn more about such outdoor pursuits right here!

Situated at the most northwestern point of Rangeley Lake, in the village of Oquossoc (yes, you read that right), this museum introduces visitors to the past, present, and, in some cases, future of outdoor sports!

Yup, this small, but delightful, museum is packed full of information that spans thousands of years of sporting history, from the Native American experience all the way to President Eisenhower’s 1955 visit, making this the perfect place to visit during any road trip to Maine.

What To Eat In Rangeley Lake

The red onion.

This place serves all of the home-cooked Italian food you could ask for! So, expect to find pizza, pasta, spaghetti, burgers, wraps, meatloaf, salad, and even steak! Yup, just an all-around cute, family-owned place that was first pulled into position by horses back in the early 1900s.

Since then, they’ve enjoyed a stable little spot in between City Cove and Haley Pond, where they’ve managed to expand and add a few more amenities, including the main dining area and bar!

Classic Provisions

This is another family-owned and operated store that also has a breakfast and lunch menu for anyone who wants to take a load off and enjoy the atmosphere of a cozy restaurant.

Everything here is seasonal, and the owners are proud to provide meals made from fresh, locally sourced ingredients. And if you like a dish enough, you can always buy the ingredients off the shelves and make it yourself once you get home!

Where To Stay In Rangeley Lake

Rangeley saddleback inn (rangeley).

Just down the road from the above eateries is the Rangeley Saddleback Inn . This warm and welcoming hotel comes with its own indoor saltwater pool, hot tub, fire pits, and barbecue grill. There are also several pet-friendly rooms for anyone traveling with their best good boys and girls!

Rangeley Town & Lake (Rangeley)

⭐️ Rating: 8.3/10 (460 Reviews) Price: $185 per night 📍Location: 2668 Main Street, Rangeley, ME Details: Read more on booking.com now!

Rangeley Town & Lake motel is perfect for those looking for affordable yet comfortable accommodations during their road trip to Maine. Everything about this place says “feel at home”, from the wood-paneled walls to the cozy furnishings and décor.

“The room over looked the lake. There were chairs to sit and visit neighbors on the open walkway. The open field had ducks running around and going to the lake. The bed was comfortable. The room was equipped to allow a longer stay and next time we will.” Gregory (read more reviews)

The view of the lake is also excellent, and the location is within walking distance of everything you might want to see or need!

Road Trip To Maine FAQ

What is the best month to go to maine.

September is the best time to visit Maine. This is because the crowds have left after the Labor day holidays so the touristy locations are not very crowded. Accommodation is also so much cheaper during this time because the demand has dropped considerably.

The weather on the other hand is still great. It hasn’t got chilly yet and you can see the start of the fall foliage before the next season’s crowds head in. In fact, the weather is still warm enough to even head out for a swim if you are in one of the coastal towns of Maine .

What Is The Best Time To Visit Maine For Lobsters?

Lobsters are available all year round in Maine so you really can’t miss them irrespective when you head to this gorgeous state. The largest catches of lobster however are caught between June and December.

How Many Days Do You Require For A Road Trip To Maine?

Honestly, there is just so much to see in Maine. It is hard to just narrow down on a few spots. A 10 -15 day trip however will strike a great balance between seeing a lot of Maine and getting some relaxation done edgewise.

What Is The Cheapest Month To Travel In Maine?

If you want a budget trip and you want good weather, then I highly recommend heading to Maine in the shoulder season which is between mid September and mid October. This avoids the Labor day crowds.

This is the time you will find the lowest rates on travel, accommodation, rentals and tours. So make the best of it!

Map of the Best Road Road Trip to Maine

Additional Resources You’ll Love

• 13 Best Breweries in Portland Maine
• 10 Amazing Scenic Drives in Maine
• 15 Best Things to do in Bar Harbor Maine
• 15 Best Things to do in Boothbay Harbor
• Best Things to do in Portland Maine
• Best New York to Los Angeles Road Trip

Well, there you have it! That just about wraps up my tips for planning an amazing road trip to Maine!

Tell me, did your fave stop on your maine road trip itinerary make the cut if not then let me know in the comments below so i can check it out., and if you found this post helpful, be sure to join our email list and pin this post now so that you can read it again later.

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Boston to Maine Road Trip

With its natural beauty, scenic vistas, and charming small towns, it's no wonder that coastal New England is the setting for one of America's classic road trips. To see the top sights and experience the best of coastal New England, you'll want to start your drive in Boston and end in Bar Harbor, Maine. Follow this guide to plan the ultimate weekend road trip from Boston to Maine. 

Drive time from Boston to Bar Harbor:   approximately   5 hours and 30 minutes Distance from Boston to Bar Harbor: approximately 295 miles Best car for this road trip:   Standard SUV

Start Your Reservation Today

Boston is the ideal spot to start this coastal New England road trip. Get an early start and enjoy a coffee as you stroll through the city's historic Italian North End neighborhood. Sit down for a morning bite at Theo's Cozy Corner Restaurant or Anthony's Café on the Waterfront before exploring a few of Boston's highlights.

To experience over a dozen of the city's key attractions in a short period of time, set out on foot and follow the Freedom Trail . This well-marked walking route includes North End sites like Copp's Hill Burying Ground, the Old North Church, and the Paul Revere House before tracing a path through the heart of Boston. As you follow the path, you can explore historic Faneuil Hall where patriots met to plan the Revolution. Here you can also visit the Old State House and explore the Granary Burying Ground. Finish with a quick tour of the Boston Common before heading north.

Rent a Car in Boston

2. Portsmouth

After leaving Boston, follow Interstates 93 and 95 to Portsmouth, one of New Hampshire's most engaging seaside towns. This waterfront setting has served as a key Atlantic Ocean port for centuries. It is filled with majestic mansions and modest homes, many of which date back to the 18th century.

If history piques your interest, make your way to the Strawbery Banke Museum . It is filled with exhibits that explore the cultural history and everyday life of Portsmouth from the 17th to 19th centuries. If art is your affinity, peruse the downtown galleries or check out the latest display at the Portsmouth Music and Arts Center.

3. Kennebunkport

Next, get back on Interstate 95 and head north to Kennebunkport, which is just over the Maine border. One could easily spend a leisurely week here browsing the boutiques and relaxing on the beach, you can still see the best of Kennebunkport in a brief visit.

First, make your way to Dock Square, located in the center of town. Here you can pick up a few souvenirs, view ocean-inspired artwork in the many galleries, and lounge on a sunny patio. After a cup of coffee and a bite to eat at Dock Square Coffee House, head to town-favorite Gooch's Beach and enjoy the sea breeze.

4. Portland

After another 40 minutes on Interstate 95, you'll arrive in Portland, Maine's biggest and most vibrant city. Park in Old Port and spend an hour or two getting lost among the 19th-century warehouses, unique shops, and intriguing museums that line Congress Street. Treat yourself to the raw bar at Eventide Oyster Co . and explore the neighboring Arts District, home to the Museum of African Culture and the Portland Museum of Art.

Before getting back in the car, make a quick stop at the Eastern Promenade, one of Portland's most scenic areas. Located just north of Old Port, the Eastern Promenade stretches for about two miles along the waterfront, offering lovely views of the sea and plenty of space to get some exercise on the walking trails. If you want to do a little sunbathing or swimming, head to East End Beach, the only public beach in Portland.

When you're ready to hit the road again, take scenic U.S. Highway 1. You'll get frequent glimpses of the sea and have great opportunities to pull over and experience life along this wild coast.

5. Bar Harbor

When you pull into Bar Harbor, you'll be enchanted by this small seaside town. Here you can watch sailboats in the waterfront and then stop by West Street to marvel at some of the mansions.

Next, head to the town's main drag, a buzzing strip where you'll find countless boutiques, souvenir shops, and ice cream stands stretching several blocks inland from the Mount Desert Narrows. If you love seafood, you'll easily find a dozen or more lobster shacks and fish houses to choose from. Indulge in clam chowder at Geddy's or enjoy lobster and oysters at the Fish House Grill.

You'll want to get up early to catch a sunrise from Cadillac Mountain in neighboring Acadia National Park . Spend the morning or the entire day hiking, biking, or swimming in this beautiful national park. If you visit during the summer, sign up for an unforgettable ranger-guided bike tour or a cruise through Frenchman Bay.

After a gorgeous day in Acadia National Park and a leisurely meal in Bar Harbor, you'll want to stay in town for at least another evening. Hop back in your rental car and explore even more of Bar Harbor and coastal Maine the next day.

See all road trips

Boston to Maine FAQs

What is the best time of year to visit Maine?

June through August is a great season to go to Maine. Temperatures during these months are great, ranging from the mid to high 70s. The chances of rain are also lower during this time. There are plenty of local events going on throughout the summer, plus it's a great time to whale watch along the coast. 

What should you not miss in Acadia National Park?

Although any part of Acadia will leave you amazed, there are some must-see spots throughout the park. Take a drive along the Park Loop Road, which wraps around Mount Desert Island and provides access to beaches and trails. Cadillac Mountain is another can't-miss attraction in Acadia. It is the tallest mountain on the North Atlantic seaboard and provides a beautiful vantage point to watch the sun set. 

What can families do at night in Boston?

There are several attractions best seen at night that the whole family will enjoy, like:

• -  The Skywalk Observatory , a 700-foot tall tower that provides a panoramic view of Boston.
• -  Bova's Bakery , which is open 24 hours a day with treats like baked bread, pastries, and pizza. 
• - Take a sunset boat tour to see the beautiful Boston harbor.

Planning a New York to Maine Road Trip Itinerary

W hether you are going for the beaches and the lobster rolls, or trying to hit peak fall foliage and everything pumpkin and apples, May through October is the perfect time to plan a New York to Maine road trip.

While it is tempting to rush through Southern New England on your way from New York to Maine, take some time to stop and see the sights along the way. This New York to Maine road trip itinerary was designed for a one-week trip, but can easily be extended to include more time at each destination or you can continue up the Maine Coast to see more of Vacationland.

This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston itinerary for additional ideas.

Or, if you want to see more of Maine, you can continue north for a road trip through the Maine Highlands . This itinerary will take you from New York City to Maine, with stops in:

• Mystic, Connecticut
• Newport, Rhode Island
• Boston, Massachusetts
• Portland, Maine

New York to Maine Road Trip

If you are taking a New York to Maine road trip, the quickest route will be under six hours through Hartford, Connecticut. This makes the best return trip from Maine, but on your way, I’d recommend taking a slightly longer and a smidge more of a scenic route on your way to Maine.

From New York City, take Interstate 95 approximately 3.5 hours (traffic can vary) to the historic seaport town of Mystic, Connecticut. If you need a pitstop along the way, downtown Stamford and New Haven both offer great dining options, or grab some lobster rolls at Ford’s Lobster in Noank, Connecticut.

Stop #1: Mystic, Connecticut

Your first overnight stop should be in the charming seaside town of Mystic. I’m not sure if it is more famous for Mystic Pizza, the 1988 film starring Julia Roberts, or the historic Mystic Seaport, a must-see family attraction. You will probably want to stay here for two nights, as there is plenty to do in town and nearby.

Mystic Seaport is a recreated 19th Century seafaring village, complete with ships, shops, and workplaces staffed with costumed interpreters ready to tell you about their craft and day-to-day life in a 19th Century town. The cooperage, print shop, and general store are all popular stops with kids. Visitors can also step on board the Charles W. Morgan, the last wooden whaling ship in the world, or get out on the water on a Mystic River boat ride.

Downtown you can grab an ice cream and watch the drawbridge go up and down as ships pass by, browse the shops, or get something to eat at one of the many seafood restaurants. In addition to Mystic Pizza, I’m a huge fan of the Engine Room for lunch or dinner, or Kitchen Little for breakfast.

Kids will also love watching the beluga whales at the Mystic Aquarium or exploring the trails at the Denison Pequotsepos Nature Center. If you are visiting in the fall, it is worth waiting in line at B.F. Clyde’s Cider Mill for some hot, fresh apple cider donuts.

If you have time to spend a couple of days, nearby you can enjoy a ride on the Essex Steam Train, a visit to the Pequot Museum on the land of the Mashantucket Pequot Nation, a lighthouse tour from New London, a day at the beach in Misquamicut State Beach in Westerly, Rhode Island, or some wine tasting at Jonathan Edwards Winery near Stonington, CT.

Read more: things to do in Mystic with kids

Where to stay: Hyatt Place Mystic (includes free breakfast) and Mystic Marriott Hotel & Spa (not in downtown Mystic but a good full-service hotel option).

Stop #2: Newport, Rhode Island

From Mystic, it is about one hour drive to your next stop in Newport, Rhode Island. You can potentially just visit for the day and continue on to Providence or Boston, but staying overnight will give you more time on the Classic Coast.

Whether you are visiting in the spring, summer, fall, or winter , there is always something to do in the historic town of Newport, Rhode Island . Once a summer getaway for the wealthy New York industrialists, Newport still attracts the yachting crowd as the “sailing capital” and the classic coast. You can do Newport in a day, as it is only an hour from Mystic, but if you want to enjoy nearby beaches, farms, or take a day trip to Providence, Rhode Island , plan on staying one to two nights.

Two must-do things when you are in Newport are paying a visit to at least one of the famous Newport Mansions and getting out on the water for a sailing tour. The Newport Mansions are former homes of the business titans like the Vanderbilts, which were once used as “summer cottages” but more closely resemble palaces than a beach house. The largest and most famous is The Breakers, but I also enjoy visiting Marble House.

If you don’t want to tour the homes, take a drive down Bellevue Avenue to see them from the front and then walk along the three-mile Cliff Walk to get a glimpse of some of the backyards, along with gorgeous ocean views.

There are many sailing options in Newport, from sunset schooner sails to seal-watching eco-tours (in the winter). Leave time to enjoy shopping and strolling along Thames Street and Broadway in downtown Newport. You can also pop into the International Tennis Hall of Fame or one of two car museums around town. There are plenty of options for a great meal, including Bowen’s Wharf, the Black Pearl, Diego’s, and Midtown Oyster Bar.

In the evening, be sure to take a drive along Ocean Drive and try to catch a sunset from either Brenton Point, the Lawn at Castle Hill Inn, or Newport Island Harbor Resort on Goat Island. On your second day, either hit the beach (my favorites in Newport are Gooseberry Beach and Second Beach) or take a drive over to the neighboring island of Jamestown to visit my favorite spot in Rhode Island, Beavertail State Park. If you prefer an urban outing (or if you are visiting on a Waterfire night), head up to Providence for the day or afternoon/evening.

Where to stay: Newport Marriott has a great location and nautical decor, The Brenton Hotel is a hip hotel in central waterfront location, and The Vanderbilt is an upscale, historic property with a great rooftop bar.

Stop #3: Boston, Massachusetts

When it is time to bid adieu to Rhode Island, drive two hours north to Boston. Now if you have extra time, you will want to spend three days in Boston, especially if you want to take some day trips to Gloucester , Rockport, or Salem, or stop at Plymouth along the way.

Boston is rich in history and charm, and like any large city, it has its fair share of great museums too. If you are interested in history, taking a walk along the Freedom Trail is a must-do. Of course, you may get more out of it if you sign up for a tour with a costumed guide.

To better understand Boston’s pivotal role in the Revolutionary War and founding of the country, pay a visit to the Boston Tea Party Ships & Museum . Kids will especially love tossing the tea into the Boston Harbor or a snack at the tea shop.

Within a short walk of the Boston Tea Party Museum, you can also visit either the Boston Children’s Museum or the New England Aquarium. If you are visiting in the summer, I’d recommend booking a whale-watching cruise in advance for an afternoon on the water and a glimpse of some magnificent creatures. If you don’t have time for a whale watch, you can still enjoy some time on the water with a harbor cruise or a ferry around the Boston Harbor Islands.

Afterward, take a walk along the Rose Kennedy Greenway and either enjoy some of the food trucks congregated there, or walk over to the North End, Boston’s “Little Italy” and pick up some cannoli at Mike’s Pastry. And while it is touristy, the street performers around Fanueil Hall are always entertaining and there are plenty of places to grab a quick bite. For a more upscale food hall, drop into the Boston Public Market or head across town to Eataly Boston.

Sports fans should try to book a tour of the “Green Monster” and Fenway Park or try to catch a Boston Red Sox game in this classic stadium. If you appreciate art, visit the Museum of Fine Arts, or the intriguing Isabella Stewart Gardner Museum nearby (and learn about the famous heist that took place there.)

While you are in town, take a stroll through the Boston Common and Public Gardens, and take a ride on a Swan Boat before you visit the famous “Make Way for Ducklings” sculpture. You can also pop into Cheers on Beacon Hill and see if anyone knows your name. Movie and television fans would also enjoy a tour with On Location Tours of popular Boston filming sites from Good Will Hunting, Ted, The Departed, and others.

Read more: Things to do in Boston with teens

Where to stay : Boston is notoriously pricey, so for a family, you may want to consider one of the following options: Residence Inn Boston Downtown/Seaport Hotel has a convenient location to downtown, North End and harbor; Element Seaport is in newer seaport district with family size rooms; and Hyatt Place Boston/Seaport District has free breakfast and a good location in popular Seaport District.

Stop #4: Kennebunkport, Maine

On your way to Portland, head two hours north of Boston to the charming coastal town of Kennebunkport, Maine. As soon as you pass into Maine, get off the highway and hightail it to Bob’s Clam Hut for some of the best lobster rolls and fried clams in New England. Then meander up the coast, taking your time to stop into a few of the best towns in the Maine Beaches region.

If you need to stretch your legs, stop in York for a walk along the 1.5 mile Cliff Walk or stock up your kitchen pantry at the Stonewall Kitchen company store. Another must-stop destination on your road trip to Maine has to be in Cape Neddick at the Nubble Lighthouse. Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door or Dunne’s Ice Cream down the street.

Just a little further along you will arrive in Kennebunkport (you might want to drive past the Bush Family compound along the way.) In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack.

We also like to head out of town to Cape Porpoise Chowder House, which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. You can stay in Kennebunkport or drive another 40 minutes to Portland, Maine. Your final destination on this New York to Maine road trip.

Where to stay: The Boathouse is a waterfront hotel right in Dock Square is perfect for when you want to be in the center of the action. If you prefer a bed and breakfast, try the The Inn at English Meadows .

Stop #5: Portland, Maine

Portland , Maine is one of the best small cities on the East Coast . Plan to spend at least a couple of days exploring Portland and the surrounding area. The park and area around Portland Head Light in Cape Elizabeth is a perfect spot for a picnic and to clamber over the rocks and watch the boats go by. When you are there, be sure to pick up a lobster roll from the Bite into Maine food truck.

Back in Old Port, take an afternoon to explore the boutiques along the harbor and wharves. There are so many amazing restaurants in Portland to try including Luke’s Lobster, Duckfat, Eventide, and Fore Street. There are also many craft breweries in the Portland area and you can board the Brew Bus for a tour if you don’t want to risk driving.

On your second day, you can take a ferry around the Harbor Islands or try a lobster cruise where you learn all about lobster fishing and even get to keep and cook what you catch. Or, spend a day shopping up in Freeport, home of the flagship L.L. Bean store.

Read more: Things to do in Portland in winter

Where to stay: Press Hotel or the AC Hotel Portland

While this New York to Maine road trip itinerary only takes you into Southern Maine, it is easy to extend this to head up to the coast with a stop at either Boothbay Harbor or Rockland before reaching Bar Harbor and Acadia National Park .

This road trip gives you a great introduction to Southern New England and includes some of the region’s highlights. If you are looking for more road trip ideas and want to dig a little deeper into New England, I’d recommend:

• New England road trips to take in the fall
• Vermont road trip itinerary
• Off-the-beaten path Maine road trip

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The post Planning a New York to Maine Road Trip Itinerary appeared first on We3Travel .

U.S. tourist faces 12 years in prison after taking ammunition to Turks and Caicos

An Oklahoma man faces up to 12 years in prison on a Caribbean island after customs officials found ammunition in his luggage.

Ryan Watson traveled to Turks and Caicos with his wife, Valerie, to celebrate his 40th birthday on April 7. They went with two friends who had also turned 40.

The vacation came to an abrupt end when airport staff members found a zip-close bag containing bullets in the couple's carry-on luggage. Watson said it was hunting ammunition he had accidentally brought with him — but under a strict law in Turks and Caicos, a court may still impose a mandatory 12-year sentence.

"They were hunting ammunition rounds that I use for whitetail deer," Watson told NBC Boston in an interview conducted last week that aired after their first court appearance Tuesday.

"I recognized them, and I thought, 'Oh, man, what a bonehead mistake that I had no idea that those were in there,'" he said.

The couple were arrested and charged with possession of ammunition. Authorities seized their passports and explained the penalties they faced.

Valerie Watson said in the interview: "When I heard that, I immediately was terrified, because I was like we can't both be in prison for 12 years. We have kids at home, and this is such an innocent mistake."

The charges against her were dropped, and she returned home to Oklahoma City on Tuesday after the court hearing to be reunited with her two young children.

"Our goal is to get Ryan home, because we can’t be a family without Dad," she said.

The couple also spoke about the financial burden of a much longer-than-planned trip. "This is something that we may never recover from," Ryan Watson said.

The U.S. Embassy in the Bahamas issued a warning to travelers in September about a law that strongly prohibits possession of firearms or ammunition in Turks and Caicos, an overseas British territory southeast of the Bahamas that is a popular vacation spot.

It said: "We wish to remind all travelers that declaring a weapon in your luggage with an airline carrier does not grant permission to bring the weapon into TCI [Turks and Caicos Islands] and will result in your arrest."

The embassy added: "If you bring a firearm or ammunition into TCI, we will not be able to secure your release from custody."

The embassy and the government in Turks and Caicos did not immediately respond to requests for comment.

The same thing happened to another American, Bryan Hagerich, of Pennsylvania, who was arrested after ammunition was found in his luggage before he tried to board a flight out of Turks and Caicos in February. He said he accidentally left it in his bag.

Hagerich was on a family vacation with his wife and two young children but has now been in the country for 70 days. He spent eight days in prison before he posted bail.

"It’s incredibly scary. You know, you just don’t know what the next day may bring — you know, what path this may take," Hagerich told NBC Boston.

"You know, it’s certainly a lot different than packing your bags and going away with your family for a few days. It’s been the worst 70 days of my life," he said.

Hagerich, once a professional baseball player, was drafted by the Florida Marlins in the MLB 2007 June amateur draft from the University of Delaware.

His case goes to trial May 3.

Patrick Smith is a London-based editor and reporter for NBC News Digital.

Abbey's Road: How an anonymous gift of new bib overalls showed me generosity

Once upon a time, not so long ago, I was admiring online a pair of floral-bib overalls that were way out of my price range and felt, frankly, quite extravagant for a person who buys most of her clothing from thrift stores.

They were made by a company I admire because it uses actual, real-life women in its ads — women who do gritty stuff, like heaving crates of vegetables into the backs of pickup trucks, standing at the helm of fishing boats with water splashing up over the sides and going on hikes in the remote regions of the Rockies; stuff like that.

So this company makes a pair of gardening overalls with flowers and gnomes all over them, and I’ve admired this particular pair of overalls for a long time, knowing I would never be willing to spend the money on them, but also that if I were to win the lottery and give some to God, some to the bank and some to my kids’ college funds, and if I had any left over after that, this pair of bibs would be my first priority.

Abbey's Road: How a spring break library trip led to a purr-fect addition to the Roy family

Since Facebook already knows all this about me and baited me with an ad one afternoon, I decided to cave and posted the following on my page, along with a photo just for fun:

“I mean I already have dreams of becoming a Fargo Trading Co. model because those ladies rock, but if they would pay me with these overalls (in a long inseam) I would be set for life.”

It was a fun post, not meant to accomplish anything except acknowledging that I like goofy gardening overalls, even if I can’t afford them.

I figured that would be the end of the story, until I was checking my email that evening and saw one that gave me pause:

“Bill has sent you an e-gift card for (insert dollar amount of overalls here) from Fargo Trading Co.”

I called my dad, whose name is Bill, right away.

“Dad, thanks so much! You really didn’t have to do that.”

“Do what?” he asked.

“Send me a gift card for those crazy overalls I posted on Facebook! You didn’t have to do that. But it was really nice of you!”

“Ab, I don’t know what you’re talking about.”

“You didn’t send me a gift card for (insert dollar amount here)?”

“Nope, I did not.”

Awkward silence.

“OK then. Gotta go!”

“Good luck!”

Abbey's Road: Witnessing history with loved ones during a once-in-a-lifetime solar eclipse

I went back and reread the email, then found where it included an email address where I could send a thank-you. After looking that one over, I unwittingly figured out the mystery gifter, who had chosen to use a pseudonym in order to remain anonymous.

I sent them an email of thanks and told them that their generosity was an encouragement to my heart; that whenever I put on the overalls, I will remember to likewise be generous.

The pattern on them reminds me of someone special — a fellow outdoorswoman who has since passed away but who I know would have worn the bibs equally well. So well, in fact, that I can distinctly picture her in them.

All of this I shared with “Bill,” whose generosity came during a hard week and was just the bright spot I needed.

In the weeks since the overalls came, I’ve been able to wear them in my garden, dividing up plants to share with others and to the ice rink during my kids' practices, where they’ve brought smiles and questioning looks to faces who either know the story behind them or don’t.

I guess if I’d have won the lottery and bought them for myself, I could feel proud or goofy or whatever when I put them on.

But this is infinitely better, because whenever it’s a bibs day, I remember “Bill’s” generosity and it prompts me to be generous.

I like to tell the story because it reminds me that generosity doesn’t come with a (insert dollar amount) price tag, either. It doesn’t cost money to speak into someone’s life; buying a cup of coffee can be relatively inexpensive; passing along plants from your garden is basically free.

A lot of it is about the posture of your heart on any given day: Are you looking for someone who could use a kind word or a cup of coffee today? What are you going to do about it — I include myself in this exhortation — to make the world feel a little bit more beautiful? 

This is your reminder to be like “Bill.” Go and do that thing today. You never know who might need it.

P.S.: The name of actual company has been changed because I prefer to live my life in relative obscurity.

Abbey Roy is a mom of three girls who make every day an adventure. She writes to maintain her sanity. You can probably reach her at [email protected] , but responses are structured around bedtimes and weekends.

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Singer-songwriter Taylor Swift released her 11th album, “The Tortured Poets Department,” on April 19, and the response to it just about broke the internet (along with a streaming record).

During all of the excitement, we unearthed a trove of Press Herald photos of Swift from when she visited Kennebunkport in 2010 for a special outdoor performance.

Check out these sensational images from staff photographer Derek Davis and then try your luck at our Taylor Swift quiz!

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