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21 Magical Winter Things to Do in Boston—Local’s Guide

Boston is known for its harsh New England winters, from bone-chilling temperature to knee-deep snow. But, the season can also be really magical with the holiday lights, snow sports, markets, and warm drinks.

After living in Boston for three winters, I’m happy to report that it’s not all gloom and doom, and there are many things to look forward to. In this post, I’ll share some of the best things to do in winter in Boston, organized in two sections by outdoor and indoor activities.

Table of Contents

Outdoor Things to do in Winter in Boston

1. go ice skating.

Frog Pond in the Boston Common is perhaps the best-known ice skating option in the city, but did you know that you can go skating indoors for FREE in the city’s public rinks? If you don’t own skates, many public rinks let you rent them for a low price. Just call ahead to ask, and double-check their online schedules for public skating hours.

Here are Boston’s public indoor ice skating rinks. They’re located across the city and beyond, so you may even have one in your neighborhood!

• EHO – Charlestown
• Steriti – North End
• Devine – Dorchester
• Murphy – South Boston
• Bajko – Hyde Park
• Reilly – Brighton

The outdoor ice skating rinks in Boston include:

• Frog Pond – Boston Common
• Skate @ Canal District Kendall – Cambridge
• The Rink at 401 Park – Fenway
• Kelly Outdoor – Jamaica Plain (public – free admission with rentals for a small fee)

Just keep in mind that non-public rinks charge both an admission and rental fee. Some rinks may also require online reservations.

Frog Pond is the most classic option, and for good reason. You get to skate right in the Boston Common with the city as your backdrop. That said, it’s also the most crowded. The ice gets scratched up easily, and it can be hard to get around if you need to hold onto the edge of the rink.

Skate @ Canal District Kendall is right near the Kendal Square T stop, giving you access to lots of great restaurants where you can grab a bit after your skate session. They also offer private and group lessons.

The Rink at 401 Park is hosted by REI and is located between Time Out Market Boston, home to several food vendors, and Trillium Fenway, a brewery. There are also several popular restaurants and bars in the area, and Fenway probably has the most active nightlife of these non-public outdoor rinks.

Kelly Outdoor Rink is close to the Stony Brook T stop, and admission is free, with rental skates costing just a few bucks. There’s not as much nearby, but if you take a 15-minute walk to Hyde Square, you’ll find some great local restaurants.

2. Enjoy a holiday cruise around the Boston Harbor

Available in December, this holiday cruise is the perfect way to get in the festive mood. Listen to holiday tunes while sipping hot cocoa and admiring the Boston skyline at night. Tickets cost $37-56 per person.

3. Wander in the snow

Boston Public Garden and Louisburg Square in Beacon Hill

There’s nothing more magical than walking through downtown Boston in the freshly-fallen snow. Stop by the Boston Common, Public Garden, Beacon Hill, and Back Bay for the best snowscapes.

See my guide to the most Instagrammable places in Boston for more photo spot suggestions.

4. Enjoy the SoWa Winter Festival

Home to art studios and boutiques in old warehouses, SoWa is a neighborhood in the South End that’s about as hipster as you can get. Every winter, they have a festival that includes an expansive holiday market, live music, art galleries, and food trucks.

The holiday market is indoors in SoWa’s Power Station, an old power plant turned event space. The industrial and modern interior is especially charming with the light displays. There are countless vendors, ranging from local foods to upcycled clothing. On the second floor, there’s a bar with live music. Tickets cost $10 at the door (paid by card only), and it’s certainly worth a visit.

If you stop by the Winter Festival on a Sunday, you should also stop by the SoWa Vintage Market for some unique knickknacks.

5. Visit Snowport

Snowport is another winter festival, but in Seaport, also an up-and-coming neighborhood in Boston. Their holiday market is outdoors and features similar small businesses, but there’s a larger emphasis on food and drink that you can buy and enjoy in heated tents.

Outside of the holiday market, there’s also a tree market that will deliver your tree to your home, as well as a a place to go curling. Don’t forget to take a stroll along the Boston Harbor as well and snap some shots of the skyline!

6. Admire the holiday lights or go to a Christmas tree lighting

Go on a walk through the city and admire the beautiful light displays. Some popular spots include:

• Christopher Columbus Park—the archway is covered in lights and is very romantic
• Faneuil Hall—go shopping or grab a bite to eat while admiring the indoor and outdoor decorations
• Commonwealth Avenue Mall—the trees with holiday lights frame the Public Garden perfectly
• Somerville Illuminations Tour (the locals are known for elaborate lighting displays)
• ZooLights at Stone Zoo

If you’re looking for impressive Christmas tree displays and lightings in particular, here are some to look out for:

• Light Up Seaport (there is also a Menorah lighting)
• USS Constitution tree lighting
• Faneuil Hall tree lighting
• North End tree lighting

A great bonus is that many of these events come with free food or drink and music!

7. Go skiing

You don’t need to drive to the mountains to hit the slopes! The Blue Hills are only a 20-minute drive from the city. If you don’t have a car, Wachusett Mountain  is accessible by the Commuter Rail in about 2 hours (there’s a  free shuttle  from the Fitchburg station during ski season).

Of course, you’ll get better slopes and views if you make it out to bigger mountains. So, if you’re looking for extra adventure, check out popular skiing destinations Stowe in Vermont and Bretton Woods in New Hampshire.

8. Eat in an igloo

If you’re looking for a special dining experience, you can eat in a cozy igloo with the Boston skyline as your backdrop at the Envoy Lookout Rooftop Bar . They also have igloos along the Boston Harbor. Be ready to stomach a steep price, however—reservations are $400-500 for two hours, and the igloos can sit up to 8-10 people.

For a more affordable, but still special, winter outdoor dining experience, check out Bow Market’s firepit tables in Somerville’s Union Square. The cost is $5 per person. Make sure to dress extra warm since you won’t be in an enclosed space. A great benefit, however, is that you can order from any of the restaurants in Bow Market (I highly recommend the poutine at Saus, and they even have a vegan option).

9. Shop small at Bow Market

Speaking of Bow Market, there’s no better place to buy local gifts. This up-and-coming shopping and dining space is located in a former storage building. The market is dedicated to small, unique shops including a quirky gift store, vintage shop, clothing boutiques, and more.

10. Go sledding

The thick snow may be the bane of every Bostonian’s existence as they walk or drive, but there’s no doubt that the snow makes for great sledding. Grab your family or friends and head over to these popular sledding spots:

• Corey Hill Park (Brookline)
• Arnold Arboretum (Jamaica Plain)
• Danehy Pond (Cambridge)
• Flagstaff Hill (Boston Common)
• Sugar Bowl at Jamaica Pond

11. Visit the New Hampshire Ice Castles

While not in Boston, these awe-inspiring Ice Castles are just a 2-hour drive away in rural New Hampshire. Made entirely of thousands of hand-placed icicles, the Ice Castles are a work of art that you can physically explore through its caverns, tunnels, archways, and slides. If you have kids, they’ll certainly be delighted.

Beyond the Ice Castles, there’s also an enchanted forest walk and small tubing area that’s included in admission, which costs $20-27 per person.

If you can make it out for an entire day and also do a winter hike in the White Mountains, the Ice Castles are worth the trip. See my full review of the New Hampshire Ice Castles for more photos and info.

Indoor Things to Do in Winter in Boston

After you enjoy the outdoor activities, come inside and warm up with these wintery things to do!

12. Have a drink at cozy cafe

Grab a hot cocoa to warm your hands and body. If you’re looking for cafe suggestions, Tatte Bakery is one of the prettiest local cafe chains in the city, and they offer a mouth-watering selection of pastries. They can be found all over Boston and the surrounding suburban cities.

Cafe SuSu on Newbury Street is another aesthetic spot, and it’s actually located inside a suit store! It’s a great place to go after doing some holiday shopping in Back Bay.

13. Enjoy a festive performance

If you want a more classic experience, you could enjoy The Nutcracker or the Holiday Pops by the Boston Symphony Orchestra. If you want something a little different, try The Hip Hop Nutcracker or “A Very Postmodern Christmas” by Postmodern Jukebox.

Check the schedule of winter performances over at Boston Theater .

14. Dig for thrifted gems at The Garment District

The Garment District is a secondhand clothing store in Cambridge known for its $2/pound used clothing selection. If you’re looking for adventure (and aren’t too afraid of germs), you can sift through mounds of clothing of all sizes and styles.

If you prefer a more curated selection, they also offer vintage styles on your traditional clothing racks, but at a higher price point. They also typically offer a special section for ugly holiday sweaters!

15. See a movie at an indie theatre

Spice up your typical movie-going experience by going to Coolidge Corner Theatre  in Brookline or  Somerville Theatre in Davis Square. These independent theatres have beautiful interiors with the classic red curtains.

Both theatres are located close to T stops and have a great selection of nearby restaurants and shops.

16. Make art in a pottery or paint studio

Winter is the perfect time to work on creative pursuits indoors. Whether you’re new to art or more experienced, going to a pottery or paint studio lets you make art in a structured environment while spending time with loved ones. In fact, it makes for a great Boston experience gift .

For pottery, Clayroom in Brookline is a studio where you can paint a pre-made piece of pottery, ranging from household items like plates and mugs to decorative figurines. Once you’re done painting, the studio will fire the pottery for you, and you’ll be able to pick it up later.

For painting, Muse Paintbar in Assembly Row has an instructor guiding everyone step-by-step through a preselected painting. There is food and drink available for purchase, and all ages are welcome at most events (just double-check the listing). Afterwards, grab a bite to eat at the many nearby restaurants, or go shopping at popular retailers.

17. Go rock climbing or bouldering

When it’s harder to exercise outside with the winter cold, going rock climbing and bouldering is a fun way to stay active. Here are some gyms in the city:

• Central Rock Gym  has locations in downtown Boston, Fenway, Cambridge, and neighboring towns
• Rock Spot Gym  is accessible from South Boston
• Boston Bouldering Project  is in Somerville

Many of these places offer day passes with gear rentals for around $30, and there are climbing routes of all difficulty levels.

18. Try an escape room

Another way to work both your body and mind is to tackle an escape room. One of the best options is  Boda Borg  in Malden, which has over 20 “quests” that are basically mini escape rooms. You can try each room multiple times, with some being more intellectual and others more active.

Some other more traditional escape rooms include:

• Escape the Room  (Downtown Crossing)
• Trapology  (Downtown Crossing)
• Room Escape  (Chelsea)
• Boxaroo  (Government Center)
• Room Escapers  (Downtown Boston)

Keep in mind that most escape rooms require a group of at least 2-3 people. Costs usually range from $30-50 per person.

19. Hunker down in a board game cafe

If you’re tired of being stuck inside at home, but still want to stay cozy, venture out to a board game cafe. You can spend all day playing classics or learning new games while sipping hot drinks or snacking on comfort food.

Knight Moves is a homey spot in Brookline that has over 2000 games. The board game cafe is also near Coolidge Corner, a bustling suburban center with several shops and restaurants.

Tavern of Tales  is another option, but you must reserve a room, which can be pricey unless you have a large group.

20. Explore a new museum

Boston is known for its many museums, ranging from science to art. When the weather outside is cold and dreary, exploring a new museum is one way to lift your spirits. Some popular options include:

• The Isabella Stewart Gardener Museum  (art museum in the style of a Venetian palace with a lush courtyard)
• Institute of Contemporary Art , which overlooks the Boston Harbor in the trendy Seaport neighborhood
• Museum of Fine Arts
• Museum of Science
• Boston Children’s Museum
• Harvard Museum of Natural History
• Harvard Art Museums

If you have a local library card, you may be able to get free or discounted passes to some of these museums. Check out your library’s website for more details on picking up these passes!

21. Eat at an indoor market

As you’re wandering around the city in the cold winter weather, you may want to grab a quick drink or bite to eat. Here are some indoor markets where you’ll find a wide variety of cuisines.

• Time Out Boston (Fenway)
• Quincy Market (Downtown Boston)
• Boston Public Market (Downtown Boston

For more ways to stay warm and entertained in the winter, check out my full post on indoor things to do in Boston .

Let us know if you have any other suggestions you’d add to this list. Stay warm and cozy this winter!

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18 Best Things to Do in Boston in Winter (2024)

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Winter in Boston can be a bit daunting with its frosty temperatures, but it also brims with wonder and charm. As a local, I’ve crafted this guide to highlight the very best things to do in Boston in winter. My curated list features some enchanting activities: from admiring the dazzling holiday lights across the city to gracefully ice skating in Boston Common. And of course, I’ve also included several indoor activities, so you can stay warm and cozy amidst the Boston winter, like on a delightful hot chocolate crawl through some of Boston’s most inviting cafes.

This guide promises a journey through the best of Boston’s winter offerings. Embrace these experiences, and you just might find yourself agreeing that winter in Boston is the best time of year!

Table of Contents

18 Best Things to do in Boston in Winter

1. admire the city of boston aglow in holiday lights.

One of the most spectacular ways to experience Boston in the winter is to get outdoors. It may be chilly, but step outside to admire the lights all around, and you will be entranced. Here are a few places in Boston where you can see gorgeous, cheerful holiday lights.

• Downtown and the Back Bay

All through winter, much of downtown Boston is twinkling. Lights adorn trees, lamp posts, and buildings, making evening walks even more inviting. Take a stroll on the Boston Common, where trees are lit up in a host of different colors, (and check your travel dates to see if your trip coincides with the incredible Boston Common Tree Lighting! Cross over into the Public Garden, where the illuminated bridge and trees are absolutely romantic. Walk along the Commonwealth Avenue Mall, adjacent to the Public Garden, and you’ll be surrounded by sparkling lights that will inspire a sense of magic and wonder in you.

• ZooLights at the Stone Zoo

If you’re an animal lover, you won’t want to miss ZooLights at the Stone Zoo in Stoneham , a northern suburb of Boston. An evening trip is doubly delightful! Not only will you get to see the animals that make this space spectacular (some highlights are lions, flamingos, and Arctic foxes), but the lights will put you in festive spirits. If you don’t have access to a car but want to immerse yourself in the world of animals, visit the Franklin Park Zoo, located in Boston.

• Faneuil Hall Marketplace

Faneuil Hall hosts a spectacular light and sound show called “Blink!” during the holiday season. The marketplace is decked out with thousands of lights, and the show features animated lights synchronized to music.

Heading to Boston in search of the Christmas spirit? Don’t miss our guide to all the amazing things to do to get into the festive season and celebrate a Boston Christmas !

2. Go ice skating

In the winter in Boston, is there a better way to spend time outside than to ice skate? With numerous public, low-entry fee outdoor ice rinks, there are ample opportunities to admire the city on skates, whether you can nail a double-axel or you’re holding the sides of the rink closely. The Frog Pond on Boston Common offers daily skating with views of the Massachusetts State House and brick-lined Beacon Hill. This is a popular spot where families love to skate. Don’t forget to grab a hot cocoa after your turn on the ice.

If you’re in Cambridge (directly across the Charles River from Boston), try out the under-the-radar Skate @ Canal District Kendall , where you’ll be gliding across ice in the city’s innovation district. No need to pack skates for your trip – rentals are available at all of these locations

3. Keep cozy on a Hot Chocolate Crawl!

It’s no secret that it can get pretty cold during the winter in Boston. But that’s no problem when you’ve got a warm cup of something delicious! So put your puffy coat on and get ready to check out some (or maybe all of) Boston’s best hot chocolate havens!  Here are 5 must-visit spots I recommend.

• Thinking Cup (Back Bay, Downtown, North End)

A Boston staple, Thinking Cup serves delectable French hot chocolate. This liquid chocolate is so richland creamy that you’ll want to savor every sip slowly in Thinking Cup’s cozy digs. With three locations – Back Bay, Downtown, and the North End – you have no excuse not to stop by and have sip!

• Cacao, Jamaica Plain

This neighborhood favorite is steeped in positivity and intoxicatingly good scents. Their Dulche de Leche hot chocolate is creamy and dreamy on a chilly day! If, like many Bostonians, you enjoy an icy treat even on the frostiest of days, try the iced mocha at Cacao during your next winter trip to Boston!

• L.A. Burdick Handmade Chocolates, Downtown Boston and  Harvard Square

This stylish yet down-to-earth spot has carefully crafted specialty hot chocolates across the taste spectrum. Your palette will be pleased with any of the artisanal goods you encounter at L.A. Burdick Handmade Chocolates !

• Gates Commes des Filles, Somerville

This authentic French chocolate shop (it’s name translates to “spoiled like girls”) is located in Somerville’s hip Bow Market. The signature hot chocolate at Gates Commes des Filles is crafted with incomparable homemade whipped cream. With an owner who studied at the Cordon Bleu in Paris, you know the drinks will be tres bien !

• Brothers & Sisters, Brookline Village

An amazing array of seasonal lattes and other hot beverages (try the mulled cider or honey pumpkin latte!) await you at this local gem! Located immediately west of Boston, Brothers & Sisters Coffeehouse and Cafe is a community-driven small business with endless charm. Other great coffee shops in Boston can be found on this list.

4. Immerse Yourself in Boston History on the Freedom Trail

Covering 2.5 miles of terrain and marked in inlaid bricks, the Freedom Trai l is a walking path connecting 16 sites of historic importance in Boston. Beginning at the Boston Common downtown and winding all the way to the Bunker Hill Monument in Charlestown, you’ll enjoy it whether you’re a complete history buff or if fun facts are more your thing. Stop in at a visitor center at Boston National Historical Park at Faneuil Hall or the Charlestown Navy Yard for programs on the 17th-19th centuries and information about the area.

Also near the start of the Freedom Trail is the Boston African American National Historic site, where you can learn about the abolitionists of Beacon Hill and the ways people of color shaped Boston.

Looking for a guided tour of Boston? This list has some great options!

5. Hop on an Old Town Trolley Tour

If you want to see everything without trekking around town, winter bus tours are an excellent option. Old Town Trolley operates 90-minute guided tours most Thursdays through Sundays in the winter months. Visitors will see and learn the significance of Boston’s most famous sites all from the comfort of an enclosed trolley. Gotta stay warm during a Boston winter!

Ding ding! Get your Boston trolley tour tickets here!

PS: If you’re visiting December 2nd & 3rd, 2023, you could join in on the Mayor’s Enchanted Trolley Tour , a festive tradition that’s been going on for 27 years!

6. Visit some of Boston’s best museums

Visiting some of Boston’s many terrific museums is one of the top things to do in any season. But when you want an excuse to get away from the winter cold, these seem even better! A few recommendations:

• Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum , situated in the Fenway neighborhood, offers an unparalleled museum experience. The lush courtyard is a popular photo spot that will instantly transport you to the world of the museum’s eponymous founder. Take a tour with a docent or explore on your own and be swept away by the worldly collections and uniquely designed rooms.

• The Museum of Science 

With 130,000 square feet of exhibit and gallery space, the Museum of Science offers hours of entertainment for visitors of all ages. Among its permanent exhibits are real dinosaur fossils, New England habitats, an interactive Hall of Human Life, and Nanotechnology. Plus, new exhibits rotate through several times a year, so there’s always something exciting happening.

Boston Travel Tip: Grab a Go Boston Card or CityPASS if you’ll be visiting either of these museums (or others!). Both cards offer great discounts on some of Boston’s top attractions.

7. Head to the symphony

There is always a full calendar of events offered by the Boston Symphony Orchestra , so be sure to check out what’s coming up on the BSO calendar during your winter in Boston trip. If you’re visiting Boston in December, don’t miss the annual Holiday Pops selection of concerts. No matter what performance you enjoy, you’re going to swoon over the gorgeous interior of Symphony Hall.

8. Cozy up with a good book

Is there anything better to do on a snowy day than to curl up with a good book somewhere warm and inviting? I’ve got some recommendations for you on exactly where to do that:

• Boston Public Library 

Book lovers and design aficionados will swoon over the beauty of the Boston Public Library in Copley Square. Art and Architecture Tours, led daily, are an excellent break from the chill outside and offer a chance to learn about an institution central to Boston’s past and present. From the enchanting Bates Hall reading room to the iconic lions outside the entrance to the courtyard at its heart (not to mention the thousands upon thousands of books), you will be enchanted by the Boston Public Library.

• Beacon Hill Books & Cafe

Just steps away from the cobblestone streets of glorious Beacon Hill, you’ll encounter a small bookshop. Beacon Hill Books & Cafe is an unassuming spot, but there are wonders within! This multi-story bookshop is not only filled to the brim with excellent books and cozy spaces to read them, but they have a children’s section that is truly enchanting.

Are you a true book worm? Check out more of Boston’s best literary sites !

9. Experience winter at the Boston Seaport aka Snowport

One of the most magical winter things to do in Boston is to go somewhere that will transport you into a winter wonderland. That place just might be Snowport.

There is so much going on this time of year at the Seaport, with a full calendar of events, rooftop igloos, free curling lanes, lights galore, and perhaps best of all, the Holiday Market.

2023 will be the 3rd year of the Boston Winter Holiday Market at Snowport , and this year it will feature more than 120 vendors, an abundance of food including a new custom cocktail bar from Tuscan Kitchen, and even more festive decor than ever before. It sounds like this is one of top things to do this holiday season in Boston.

10. Visit a chocolate factory

Take a tour of the Taza Chocolate Factory – no golden ticket required! You will satiate your sweet tooth and learn something new at this Somerville spot. On a tour, you’ll learn about the chocolate-making process and have the possibility of seeing it get made. And yes, there are samples, complete with chocolate guides who will let you know what you’re tasting. This is a sweet idea for a Boston winter date!

11. Enjoy a show at the Coolidge Corner Theatre in Brookline

A local favorite, the Coolidge Corner Theatre has been around for nearly 100 years. Today, this nonprofit cinema features everything from cult cinema to big screen classics. Its art deco appearance and community-driven spirit make it a true treasure. It’s the perfect place to go for an evening activity or an extra cold or rainy winter day in Boston. 

1 2. Nosh on a gourmet grilled cheese at Roxy’s

Roxy’s Grilled Cheese sandwiches are melt-in-your-mouth amazing. These delectable melts contain so much more than cheese and bread. Try “The Allston” for a savory sweet treat or the “Green Muenster Melt” for a smoky bacon-filled dream dinner. Don’t just grab some tasty grub though. Head into the back room and you’ll step into the A4cade, an arcade and bar complete with everything from PacMan to pinball.

You Might Also Like: Weekend in Boston Itinerary

13. Find a treasure at The Garment District, Kendall Square

For the funkiest finds around, head to this “alternative department store.” Garment District , in Kendall Square, is part costume shop, part thrift shop, and part new clothing store, this place is a whole lot of fun. No matter your style, you can spend hours trying clothes and costumes on at this fun Cambridge shop.

14. Attend the SoWa Winter Festival

Every Sunday, Bostonians and visitors flock to the South End neighborhood to visit the SoWa Open Market. Here, you’ll encounter an engaging shopping experience, featuring local artists, plus food and beverage vendors. In winter, this transforms into the SoWa Winter Festival , a 15-day celebration where hundreds of vendors gather to make, sell, and share. Whether you are looking for holiday gifts or for a treat for yourself, shopping at SoWa supports local artists and offers countless unique treasures, in a beautifully illuminated space. Sounds like the perfect winter in Boston activity!

15. Eat your fill of incredible Italian food in Boston’s North End

To me, hearty Italian fare goes hand-in-hand with wintertime. Who doesn’t love a heaping bowl of pasta on a cold day? Piping hot bread savored as the winter winds whip outside? Italian cuisine is an ultimate comfort food.

In Boston, the North End is home to some of the most amazing Italian restaurants anywhere. The North End is very cool and absolutely worth a visit in general, but there’s no denying that FOOD is one of its major draws.

If you want to stuff your face on some epic meals, check out our list of the Best North End Restaurants in Boston . You won’t regret it.

Consider yourself a foodie? A Boston food tour is a perfect idea for you. Check out our whole list of Boston food tours to consider. Bon appetit!

1 6. Pamper Yourself at G20 Spa

For the perfect cold weather activity in Boston, head indoors to warm up and pamper yourself (and your date, perhaps?) at G20 Spa , one of the top spas in Boston. There are all the traditional spa treatments plus some interesting extras like an Experience Room for aromatherapy-infused steam sessions, Flotation Pod, Salt Cave, Fireside Lounge, and so much more. A couples day at the spa could be the perfect romantic thing to do on a Boston winter’s day!

17. Catch views of the Boston skyline in wintry wonder

No matter where you are in Boston, you’ll get amazing views from the vantage point of a rooftop. Restaurants , bars, and other venues offer indoor and outdoor spaces where you can admire the city in its winter finest! While shorter days can sometimes be a bummer, your spirits will be lifted when you catch the sunset and all the angles of “the Hub” from one of these spots. PS: These are all great options for Boston winter date ideas!

• Après…@ Deck 12

The much-anticipated Après…@ Deck 12 at YOTEL is making its grand return for the 2023 winter season. This innovative rooftop bar offers a cozy après-ski experience right amidst the urban buzz of Boston. Guests stepping onto Deck 12 will be greeted with an environment meticulously crafted to resemble a classic winter resort. The space boasts elements like heated gondolas, chair lifts, and snug Adirondack chairs, plus a winter-inspired menu that includes warming beverages like hot cocoa and creative specialty cocktails, along with indulgent comfort foods. YUM.

PS: This is quite close to Snowport, so consider visiting the holiday market and then popping over here après!

• Lookout Rooftop & Outlook Kitchen at the Envoy Hotel

Views and cocktails from Lookout Rooftop are superb. Pair the panoramic views of Boston Harbor from the indoor lounge or outdoor heated igloos with one of the unique craft cocktails, and the only chill thing will be the vibe!

• Dorchester Brewing Company 

Here’s a place you can grab a beer AND a view. On an industrial stretch of road in Boston’s biggest neighborhood, Dorchester Brewing Company is unassuming at first. But take a look up and you’ll notice its expansive roof deck and greenhouse-style rooftop beer hall, dubbed the “Hopservatory.” Order a house- or locally-brewed beer, wine, and cider on tap and admire skyline views of Boston from the south. Also featured on the main level of DBC are a game room and a barbecue joint, where you’ll find a menu that meets most dietary needs and desires. This is another great date spot for a fun Boston winter date night!

Situated on the outskirts of Harvard Square in Cambridge, Daedalus will delight your senses all around. Although the rooftop is just one story above ground, the backdrop of Harvard’s stately campus combined with gentle lighting and intentional greenery will lift your spirits into a mellow ambiance. The casual restaurant features interesting New American cuisine plus a bar on each level. It also has heated dining pods bestowed with twinkling lights, so no matter the weather, you’ll be comfortable. 

18. Discover the winter night sky at Coit Observatory

Okay, so you’ll be looking a *bit* above the Boston skyline when you visit the Coit Observatory – up at the stars, to be specific. This observatory at Boston University hosts Public Open Nights every Wednesday evening from 7:30 – 8:30 in the winter. Depending upon the night and the weather, you’ll have a chance to learn about and view stars, constellations, planets, the moon, and astronomical occurrences, and take a look at them through a telescope. Tickets are free but must be reserved in advance.

Where to Stay in Boston in Winter

• The Liberty Hotel

The Liberty Hotel is a unique boutique hotel that makes the perfect spot to stay in Boston during your next winter trip because it’s easily walkable to lots of great Boston things to do. It’s also a site with some pretty neat history, as it was once the historic Charles Street Jail; this is one of the coolest places to stay in Boston in winter and beyond!

Click Here to Check Prices & Book!

• The Verb Hotel

If you’re into funky, retro homage boutique hotel experiences, The Verb Hotel has you covered. This hip place to stay in Boston features rock and roll memorabilia everywhere you turn and is quite literally just steps to Fenway Park!

• The Fairmont Copley Plaza

If you’re planning a romantic winter getaway in Boston, consider booking a room at The Fairmont Copley ! This gorgeous luxury hotel is the perfect place to shack up with your sweetheart on those cold winter Boston nights.

Whatever you end up doing and wherever you end up staying during your winter trip to Boston, stay warm and have a good time!

Boston Winter FAQs

Is boston worth visiting in winter.

You may not think of winter as prime time to visit New England , but truth is, it’s gorgeous up here. With snow-dusted streets, charming holiday storefronts, and welcoming restaurants and shops to warm up, it is truly a winter wonderland in this region of the country.

And while yes, it can be quite cold, there are still many advantages to visiting Boston in winter, including fewer crowds, off-season pricing, and the charm of a snowy cityscape.

How cold does Boston get in winter?

Boston experiences cold and often snowy winters, with temperatures typically ranging from chilly to downright cold. Here is a breakdown of the typical winter temperatures in Boston:

• December: High temperatures range from around 40°F (4°C) to lows of 26°F (-3°C).
• January: High temperatures average around 37°F (3°C) and can drop to lows of 22°F (-6°C).
• February: High temperatures continue to be cold, averaging around 39°F (4°C), and lows can dip to 24°F (-4°C).

Boston in December, January, and February is also quite likely to have snow, with the city receiving approximately 44 inches each year.

If you choose to visit Boston in winter be prepared for cold weather, potentially icy conditions, and the need for appropriate clothing such as warm coats, hats, gloves, and insulated footwear. Winter storms can also impact travel plans, so it’s a good idea to monitor the weather and check for any potential disruptions if you plan to visit during this season.

Editor’s Note : You don’t need a car in Boston with its terrific public transportation system, but visiting in winter is even more reason not to rent a car, as you’ll have to contend with potential winter driving conditions. I can tell you, Boston is no picnic driving in any season, but winter is particularly stressful! – Amy

More Boston & Massachusetts travel guides:

• 10 Awesome Things to Do in Boston with Kids
• 10+ Essential Things to Do in Boston for First Timers
• Where to Go for the Best Breakfast in Boston
• 10 Ideas for a Festive Christmas in Massachusetts

A Complete Guide to Visiting Boston in the Winter, From a Local

By Author Meg Frost

Posted on Last updated: March 9, 2024

Categories Massachusetts , United States of America (USA)

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Boston in the Winter can be a wonderful time to visit, as long as you plan accordingly.

I’ve lived in this historic city for 20 years now, so I have an insight into all the best winter activities and tried-and-true tips on how to deal with the weather.

If you’re planning to visit Boston in the Winter, here’s my comprehensive guide to help you with weather tips, a packing list, and a curated selection of activities you don’t want to miss.

Weather in Boston in the Winter

A Winter trip to Boston is sure to include chilly weather with a chance of snow. Here’s what you can expect month by month, from December through February.

Weather data courtesy of the National Oceanic and Atmospheric Administration’s National Centers for Environmental Information.

Average temperatures in Boston in December typically range from 30°F to 45°F. That’s a decent range, so to narrow it down, the average temperature in December 2023 was 40°F.

The beginning of the month usually starts pretty mild, but as the month progresses, the temperatures start to drop.

Sometimes you’ll get snow, although usually it’s just flurries. That doesn’t mean there won’t be a big snowstorm though!

January brings the full blast of winter to the city! Average temperatures range from 24°F to 36°F, and we usually get a good snowstorm or two.

Every few years, though, we get blasted with a blizzard in January or February, with temps dropping even lower.

February is much like January. Average temperatures range from 26°F to 37°F and there’s bound to be a snowstorm or two.

I highly recommend getting a travel insurance policy that covers inclement weather. There’s a higher chance this time of year that you’ll have to move your trip due to ice or snowfall.

What to pack for Boston in the Winter

If you’ve decided to brave the cold and visit Boston during the winter season, packing smart is essential.

To put it simply, layering is your best friend. Here’s a comprehensive packing list to ensure you’re prepared:

• Comfortable walking shoes or boots : Make sure they are warm, comfortable for lots of walking, and have a good grip. It’s best if they’re waterproof, too. Most of all, pack a minimum of two pair!
• Hats, gloves, and scarves : These warm layers can be added or removed as needed.
• Winter coat : A waterproof coat is best, in case you get met with snow or rain, but above all, make sure it’s warm!
• Casual layer-able clothing : Unless you have a fancy event to attend, you can stick to casual wear. Bring clothing that you can layer so you don’t get too hot or cold.
• Warm socks : Opt for moisture-wicking materials that dry quickly, like wool.
• Lip balm and moisturizer : The dry winter air is no joke here. Moisturize, moisturize, moisturize!
• Small backpack or day bag : Bring something easy to carry and will fit what you need for the day.
• Camera or smartphone : You’ll want to record all of your fun memories!
• Portable phone charger : Stay charged up throughout the day with a power bank.
• Waterproof, insulated snow boots : Check the weather before you leave, as this might be overkill.
• Thermal underwear : If you’re not used to the cold, you may want to wear thermals under your clothes for added warmth.
• Hand and toe warmer inserts : These are great to have on hand if you’ll be outside lots.

Things to do in Boston in December

Boston goes all out in December when it comes to the Winter holidays! There’s no shortage of events for Christmas, Hannukah, and Kwanzaa!

Here are my top picks for things to do in Boston in December.

Shop for the holidays

Get your holiday shopping done in style along Newbury Street in Boston’s Back Bay. This famous shopping street is lined with boutiques, art galleries, restaurants, plus many of your favorite chain stores.

For a more festive atmosphere, check out the Seaport Holiday Market at Snowport and the SoWa Winter Festival in the South End.

These vibrant pop-up markets offer unique, handcrafted gifts and plenty of snacks from local vendors.

See the holiday lights

Boston twinkles with festive lights during the holiday season.

Explore places like the Boston Common, the Commonwealth Avenue Mall, Copley Square, and Faneuil Hall Marketplace, which are adorned with a myriad of holiday displays that add a warm glow to chilly evenings.

Each year, a giant Christmas tree is lit up on Boston Common, as well as a large menorah, accompanied by live music and other festivities.

Want to make a night of it? Check out the Holiday Lights Trolley , which takes you around the city to see the best light displays.

It’s BYOB for 21+ and includes a pit stop at the Snowport market for the afternoon run and Encore Casino for the evening run.

See a holiday show

There are always several good shows running throughout the area that celebrate Christmas. Here are my top recommendations:

• Holiday Pops featuring the Boston Pops Orchestra and Tanglewood Festival Chorus
• Langston Hughes’ Black Nativity – a retelling of the Nativity with a Black twist, such as Gospel music
• The Nutcracker featuring the Boston Ballet
• The Slutcracker – An 18+ burlesque version based on the original ballet

First Night Boston

Ring in the new year on December 31 at First Night Boston.

This free event includes live music, ice sculptures, a parade, fireworks, and other family-friendly fun.

Activities take place throughout the city at key spots like the Boston Common, City Hall Plaza, Downtown Crossing, and the Rose Kennedy Greenway.

For more details about this year’s city-wide party, check out the First Night Boston website.

Things to do in Boston in January

Start the new year with a winter vacation to Boston in January! Here are a few fun events to check out this month.

Boston Celtic Music Festival

This festival features traditional Irish, Scottish, and Cape Breton music, as well as dance performances and introductory music classes.

Also known as BCMFest, it usually takes place over a weekend in mid-January. For more information, check out the festival’s Facebook page .

Boston Wine & Food Festival

The Boston Wine & Food Festival is a culinary extravaganza put on by the Boston Harbor Hotel.

Each weekend, from mid-January through March, there are wine tastings, seminars, tastings, and themed brunches and dinners.

Check out the festival’s website for more information, including how to make reservations or buy tickets.

Things to do in Boston in February

Whether you’re in town for the Super Bowl or a romantic getaway, here are the top fun things to do in Boston in February.

Boston Beanpot Hockey Tournament

The Beanpot Hockey Tournament has been a Boston institution since 1952!

This tournament features the men’s and women’s hockey teams from 4 major colleges in the area: Boston University, Boston College, Harvard University, and Northeastern University.

The men’s teams typically face off on the first 2 Mondays of February at the TD Garden, while the women’s teams play on the first 2 Tuesdays with the location rotating each year between the 4 schools.

Black History Month Film Festival

Another excellent film festival in Boston in February is the Black History Month Film Festival.

Hosted by The Boston Globe, this event includes virtual and in-person film screenings and discussions featuring films that “celebrate the lives, culture, and creativity of Black Americans,” as the festival’s site states.

For more information on dates and a schedule, check out the festival website .

Boston Science Fiction Film Festival

Each February, Sci-Fi film fans flock to Somerville Theatre for screenings, panel discussions, parties, and premieres.

Recently, an online component was added on Filmocracy so fans worldwide can join in, even if they can’t make it to Boston.

Check out the festival website for dates and schedule.

Things to do in Boston in the Winter

Even with Winter’s bite, the city of Boston comes to life with seasonal events and activities that celebrate this special time of year.

Here are more must-do activities that will make your winter visit to Boston memorable, no matter when you visit during this season.

Celebrate Chinese New Year

Boston’s Chinatown hosts a Chinese New Year celebration, complete with a lion dance parade, cultural performances, and a street fair.

The date varies but typically occurs between the end of January and the end of February. The Chinese Consolidated Benevolent Association of New England (CCBA) is a good source for celebration dates and information.

Outdoor dining (hear me out…)

Yes, that’s right – you can dine outdoors in Boston in the winter ! There are a handful of spots that have heated igloos and yurts for outdoor dining that also provide a bit of privacy.

Here are a 5 top spots to consider:

• 75 on Liberty Wharf
• The Anchor Boston in Charlestown
• The Bowery Bar in Dorchester
• Deck 12 in Seaport
• Lookout Rooftop Bar at the Envoy Hotel

Ice skating

Embrace the season with ice skating. The Boston Common Frog Pond and the Rink at 401 Park offer picturesque outdoor locations for a spin on the ice.

Skate rentals are available at both locations, so no worries if you don’t have a pair of your own!

Taza Chocolate Factory Tour

Venture on a behind-the-scenes tour to learn about Taza’s stone-grinding techniques and sample their delicious chocolates.

This is a perfect indoor activity for a brisk winter day or a unique date activity!

Black Heritage Trail

The Black Heritage Trail is a 1.6-mile walk through the Beacon Hill neighborhood that highlights over a dozen important sites in Boston’s Black history and heritage.

The walk can be self-led via an audio tour from the NPS app or you can join a guided tour through the National Park Service during the Summer .

Boston Bruins & Celtics games

We’re a bit obsessed with our professional sports teams here in Boston.

If you’re visiting during the winter months, you can catch a Boston Bruins hockey game or Boston Celtics basketball game, both held at the TD Garden.

You can catch the home game schedules here: Boston Bruins | Boston Celtics.

Explore Boston’s finest museums

If outdoor activities aren’t your thing, dive into Boston’s rich history and renowned museums.

Here are the top spots to hit up this time of year:

• Boston Children’s Museum – Definitely check out their Snowmazing! indoor playground!!
• Institute of Contemporary Art – Contemporary art museum with stunning views of Boston Harbor.
• Isabella Stewart Gardner Museum – Be sure to check out their holiday courtyard garden on display from December-January.
• Museum of African American History – Learn about African American history from the 18th and 19th centuries.
• Museum of Fine Art – Browse the permanent and visiting fine art exhibitions from around the world.
• Museum of Science – Super fun, immersive museum with an IMAX theater.

What are your favorite things to do in Boston in the Winter?

Boston in the Winter brings lower crowds and for some, a romantic snowy backdrop.

On the other hand, the weather can be a turn-off for some. But if you pack smart and plan lots of indoor activities, you’ll have a great time.

Just be sure to book refundable hotels and transportation and make sure your travel insurance covers cancellations or rescheduling fees due to inclement weather.

About the author

Meg Frost is a Boston-based travel blogger that helps people embrace technology to make vacation planning and traveling wicked easy, affordable, and fun.

She holds an M.A. in Journalism from Northeastern University and B.S. in Communication & American Studies from University of Miami.

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Visitor guide, subscribe to our, e-newsletter, online store, the ultimate winter bucket list in boston, warm up to boston this winter.

Here in Boston, we embrace all four seasons. And with so much happening this  winter , we bet you'll love Boston's colder months as much as we do! Whether you're warming up at one of the city's indoor experiences or embracing the wonder of the  outdoors , there's no better place to winter than Boston.

Here's the ultimate winter bucket list to make the most out of your season and fight those winter blues:

Warm Up at One of Boston’s Best Activity Bars and Experiences  

Whether you're looking for a new way to experience Boston's  food and drink scene  or you just need a way to warm up in the winter,  Boston's best activity bars and experiences  are the perfect way. Imagine yourself on a sunny golf course at  Five Iron Golf , hit a bullseye at  Flight Club , grab your favorite draft and catch a feature film at  Alamo Drafthouse , or immerse yourself in a virtual world at  Key to Amaze . 

The fun isn't limited to Boston! Experience the same energy outside the city as you take the track at  K1 Speed  in Wilmington, uncover clues and mysteries at  The Escape Game  at Dedham's Legacy Plaza, or swing into the first-ever  TopGolf  location in Massachusetts in Canton.  

Explore the Best of Boston’s Museum Exhibits  

Boston is filled with a unique array of  history and art museums  that are home to some of the world's most famous and beautiful exhibits. This winter, these museums will host some of the most talked about pop-up exhibits of the year. 

Check out the  Museum of Fine Arts , which is known for having one of the world's most extensive art collections and will be hosting several new and  exciting exhibits  this winter that are sure to pique everyone's interest. Or, explore the personal collection of arguably one of the most fascinating women in Boston's history at the  Isabella Stewart Gardener Museum  while warming up in the museum's garden oasis. Make sure to check out our  event calendar  so you don't miss out on late-night parties, lecture series, holiday experiences, and even free admission days.  

For a more interactive experience this winter, discover a world of wonder at Boston's  WNDR Museum Downtown  or watch sparks and stars fly at the  Museum of Science . There is something for everyone's artistic and curious side here in Boston!

Enjoy ‘Hands-on’ Experiences  

Winter is the ideal time to stay inside and find or perfect a craft or hobby, and with Boston's wide array of local businesses, there are so many hands-on experiences to choose from. Grab your friends and head to Boston's South End to make your own candles at  Sky Candle's Candle Bar , or head to Newbury Street and make your own custom perfume at  Olafactory.  While you're in the South End neighborhood, join  Clay Lounge  for a pottery class or head to Cambridge to take a glassblowing and flameworking class at the  North Cambridge Glass School .  

If you're looking for a unique  date night , we recommend taking a  cooking class at Self Up , a wine course at  Commonwealth Wine School , or a charcuterie board workshop with  Boards by Mo .  

Looking for something to sweeten up your season? Take a cake decorating class with  The Sugar Connection , or head to the area's historic  Taza Chocolate Factory  for a factory tour, class, or tasting. 

Outdoor Adventures in a Winter Wonderland  

There are so many ways to experience our picturesque winter wonderland. Order a hot chocolate from  L.A. Burdick's  and walk down Newbury Street to the iconic  Frog Pond , where you can go  ice skating  in the heart of downtown Boston. Or, stroll one of the area's  parks , like the Charles River Esplanade , Arnold Arboretum , or Mount Auburn Cemetery , for a peaceful, wintery escape from the hustle of urban life. 

With so many outdoor art and light installations popping up in areas like the Rose Kennedy Greenway ,  Downtown Crossing , Newbury Street, and the Commonwealth Avenue Mall, a winter stroll is a must.

Looking for the perfect day trip? Drive a bit beyond Boston and visit some of New England's  best ski and snowboard mountains , or explore one of the area's best beaches, which are just as beautiful even when it's cold.

Find Your Academic Side  

Boston is well known for its academic institutions and history, and this season is the perfect time to immerse yourself in some of  Boston's hidden gems  and to find your academic side. 

Head to one of Boston's  most unique bookstores , such as Brattle Bookshop and Commonwealth Books. Or, visit the  Boston Athenaeum , a library, museum, and cultural center that is arguably one of the most unique and awe-inspiring landmarks in Boston and is home to over half a million books, including published works from the 1800s, the latest best-sellers, and approximately 100,000 rare books.

Chances are, you probably already had visiting the  Boston Public Library  on your winter itinerary, but did you know you could dine there as well? Book a reservation for high tea at the  Courtyard Restaurant  and enjoy their delightful selection of afternoon teas and a food menu with classics like cucumber sandwiches, smoked salmon, tea scones and French macarons. If you consider yourself more of a night owl, head to the  Map Room Lounge  for a specialty craft cocktail and savory bites and enjoy an unforgettable late-night experience.  

Have a Night at the Theater  

The city's inventory of  historic and iconic theaters  is unmatched, and there is no better time to experience them than winter. Get dressed up, grab your friends or date, and score tickets to a Broadway show, the Boston Ballet, or another theatrical performance.  

Warm up with Cozy Dining  

Winter is the perfect time to find a table at one of the  city's cozy bars and restaurants . We recommend a build-your-own bloody at  Bostonia Public House , a classic Italian dinner at  Grotto , jazz brunch at  The Beehive , or a cocktail with a view at The Street Bar at  The Newbury Hotel .  

It is also the perfect time to explore  Boston's Chinatown  neighborhood, filled with events, decorations, and festivities for the  Lunar New Year . Head to this neighborhood and warm up with Hotpot at  Q Restaurant , or Dim Sum at Hei La Moon or Winsor Dim Sum Cafe. Want to learn more about the country's third-largest Chinatown and all the hidden gems within? Then check out  Boston Chinatown Tours  to explore secret nooks, neighborhood favorites, and, of course, delicious bites. 

Enjoy a Concert at Symphony Hall  

There is no better age-old tradition than seeing the  Boston Symphony Orchestra  performing at Symphony Hall. The Boston Symphony Orchestra is the largest orchestral organization in the world and has delighted and inspired audiences year-round since 1881. With special guests, themed nights, and concerts on most Tuesdays, Thursdays, Fridays, and Saturday evenings, winter is the perfect time to journey to this historic location and immerse yourself in Boston's cultural scene.  

Looking for classical music with a more modern flare? Then check out the  Candlelight Concert  series, hosting themed musical performances featuring local performers at unique sites throughout Boston. 

View Boston from the Top  

Take in Boston's winter wonder from the 'top' of the Prudential Center.  View Boston  is a 360-observation deck offering breathtaking views from above the heart of Boston. If the astonishing views weren't enough, visitors also have the chance to find places they want to visit and mark them down to create a personalized itinerary for their time in Boston. Don't forget to stop by  Stratus  and  The Beacon  on your way out for an elevated dining and cocktail experience. 

Explore Unique Dining Experiences  

Who said dining outdoors was just for the summertime? Enjoy dinner and drinks from a rooftop igloo at the  Lookout at Envoy Hotel , or book a yurt for you and your friends at  Bowery Bar  in Dorchester. 

Go Thrift and Vintage Shopping  

Have a New Year's resolution to spend less and shop smarter? Or are you looking to fill your home aesthetic with treasures and unique pieces? Then head to one of Boston's best thrift, vintage, or antique stores!

Stroll down the streets of Boston's Beacon Hill and head to Upstairs Downstairs Home, Blessing Barn, or Elegant Findings to discover something unique. After that, venture to Cambridge for over four floors of hidden treasures at the Cambridge Antique Market or stroll the  SoWa Vintage Market  in the South End for that perfect gift. 

Head to Allston and check out Vivant Vintage, South Boston for Covet, Jamaica Plain for Boomerangs, or Cambridge's iconic Garment District for a multi-story retail clothing experience. We also recommend heading to  Somerville's Bow Market  and checking out  Blue Bandana Relics  for curated vintage menswear, industrial antiques, and Americana vibes. 

Heat Up at the TD Garden  

Boston is known as one of the best sports cities in the world, and this winter season is one of our strongest. Head to Boston's  West End  neighborhood and visit  TD Garden  to cheer on the  Boston Celtics  on the court and the  Boston Bruins  on the ice – and feel the arena heat up. 

Meet Boston Winter Promo

Book a 2-night stay at select hotels and enjoy a $100 prepaid gift card and a $25 Legal Sea Foods gift card.

Guide to Winter in Boston

Immerse yourself in our arts scene, skate on the iconic frog pond, catch a Celtics or Bruins game at TD Garden, or book an unforgettable hotel package for two - here's your guide to winter.

Join our Adventure: Get all my insider tips for traveling on a budget

The Wild Trek

22+ Best Things To Do In Boston In The Winter From A Local

Boston in winter is a magical experience. The city comes alive with holiday decorations, seasonal events, and plenty of indoor and outdoor activities. Whether you’re a local or a visitor, you’ll find no shortage of ways to embrace the chilly weather.

Today I’m sharing everything you need to know about visiting Boston in the winter from a local perspective, as well as 22+ best things to do in Boston during the winter season!

Why Visit Boston In Winter?

Visiting Boston in the winter is an experience. And while Boston is beautiful during all four seasons, there are plenty of reasons to go in the winter specifically.

One of the best things about visiting Boston in winter is that you’ll encounter fewer tourists. This means shorter lines at popular attractions and a generally less crowded experience as you explore the city. Boston can get  pretty packed in the summer, making it hard to actually experience history.

Plus, winter is generally considered the low season for tourism in Boston, so you’re more likely to find better deals on flights and accommodations. Many attractions also offer off-season pricing . The price differences can be huge.

Boston in winter is not short on things to do. From ice skating at Frog Pond to holiday markets and seasonal concerts, the city offers a host of winter-specific activities that you won’t find during other times of the year. Because we’re used to winter up here, we have  tons of activities that you can  only do during the winter. Hey, we need to get through the cold months somehow. And Boston has a rich array of indoor activities, from museums to historic sites and theaters . Winter is a great time to explore these options without feeling like you’re missing out on outdoor activities.

If you come during the holiday season , Boston is something to behold. With tree lighting ceremonies, holiday markets, and decorations all around, the city becomes a winter wonderland. If you love the holidays, Boston in winter is a perfect fit.

And if you’re a fan of winter sports like skiing, snowboarding, or sledding, there are several places within a short drive from Boston where you can hit the slopes or find a good hill for some classic winter fun. I  love how close Boston is to all New England winter sports because you can experience the winter city magic and do the rural New England thing all in one trip.

Lastly, Boston is a walkable city, and its public transportation system is efficient. Even in winter, the city is easy to get around, whether by foot or by using the T (subway). One of the perks of being a smaller city is that it’s not hard to get somewhere, even during chilly winter days.

Best Things To Do In Boston In The Winter:

Here are some of my favorite Boston winter activities that you’ll  definitely want to schedule in.

22. Ice Skating

Ice skating is one of those activities that epitomizes Boston in winter. Whether you’re a local looking for a seasonal activity or a visitor wanting to embrace the winter chill, strapping on a pair of skates is an ideal way to do it. Here’s the scoop on ice skating in Boston, including some top spots to check out.

No discussion about ice skating in Boston would be complete without mentioning Frog Pond. Situated in Boston Common, the city’s historic park, Frog Pond is transformed into an outdoor skating rink every winter. It’s perfect for skaters of all ages and skill levels. Rentals are available, and there’s a café where you can grab some hot cocoa or a snack.

This is my #1 recommended area to ice skate in Boston. Everyone should go to Frog Pond once!

Frog Pond generally opens for the winter season from late November or early December through March, weather permitting. The rink has specific hours for public skating, which can vary depending on the day of the week and whether there are any special events or private bookings.

Kendall Square Community Ice Skating:

Located in Cambridge, not too far from downtown Boston, the Kendall Square rink offers another outdoor skating experience. This rink is less crowded than Frog Pond, making it a good option if you’re looking for a more relaxed environment. They also offer skate rentals and lessons if you’re a beginner.

Steriti Memorial Rink:

Located in Boston’s North End, the Steriti Memorial Rink is an indoor option that offers free public skating. It’s particularly popular among locals and offers a view of the Boston Harbor. It’s a good alternative if you’re looking for a place to skate without braving the outdoor chill.

Warrior Ice Arena:

If you’re a hockey fan, you might want to check out Warrior Ice Arena , the practice facility for the Boston Bruins. The arena is open to the public for skating at certain times and offers a high-quality ice surface. It’s located in the Boston Landing area, which has restaurants and shops to explore before or after your skate.

21. Visit Faneuil Hall Marketplace

Faneuil Hall Marketplace is one of the prime spots to visit in Boston in winter. The historic area is transformed with twinkling lights and holiday decorations. Street performers often brave the cold, providing free entertainment as you stroll around. Don’t forget to grab some hot cocoa or mulled wine from one of the many vendors.

Shopping:   Faneuil Hall Marketplace is also a shopping destination. The area is dotted with a variety of shops, from major retail chains to quirky, independent boutiques. Whether you’re looking for souvenirs, fashion, or unique crafts, you’re likely to find it here.

Food: One of the main attractions of visiting Faneuil Hall is the food. Quincy Market , located just behind Faneuil Hall, is home to a bustling food court that offers an extensive range of options, from classic New England dishes like clam chowder and lobster rolls to international cuisine. It’s a fantastic place to grab a quick, affordable meal in the heart of the city. Outside, in the North and South Markets, you’ll find even more dining options, including sit-down restaurants and pubs where you can take a breather and soak in the atmosphere.

Winter events: Faneuil Hall is not just a summer attraction; it has a year-round appeal. In winter, it transforms into a festive wonderland complete with holiday decorations and seasonal events like the “Blink!” light and sound show. There’s often a large Christmas tree, making it a focal point for holiday celebrations in Boston.

20. Catch a Celtics Game

Sports are a big deal in Boston, and winter is basketball season. Catching a Celtics game at TD Garden is an electrifying experience and a perfect way to escape the winter chill. The crowd is passionate, and the energy is high, making it one of the best indoor activities in Boston in winter.

The Celtics play right at TD Garden , which is super centrally located and is also North Station (perfect if you’re taking the train in or out). So you can catch a game and do a few other activities if you plan right!

If you’re not from the Massachusetts area, then I  highly recommend seeing a Celtics game . There’s nothing like the New England sports atmosphere (we’re pretty intense) and the whole thing is a wild experience.

19. See The Nutcracker Ballet

When it comes to cultural activities that capture the magic of Boston in winter, seeing a performance of “The Nutcracker” ballet is near the top of the list. Performed annually by the esteemed Boston Ballet and various other local companies, this classic Tchaikovsky ballet has become a cherished holiday tradition for many Bostonians and visitors alike.

The primary venue for the Boston Ballet’s rendition of “The Nutcracker” is the historic Boston Opera House , located in the heart of the Theater District . The Opera House itself is worth a visit, boasting grand architecture and opulent interiors that set the stage for a night of elegance and enchantment. It’s one of the fanciest spots in Boston!

Tickets for “The Nutcracker” typically go on sale in the late summer or early fall and can sell out quickly, especially for popular dates close to Christmas. It’s advisable to book your tickets well in advance. The ballet usually runs from late November through December, offering multiple performances each week, including matinees that are perfect for families. Even if you’re not a huge fan of the ballet, I highly recommend going to see the Nutcracker just to experience the Opera House atmosphere! Plus, you get to dress up, which you won’t find many other places in Boston (it’s a casual city, especially in the chilly winter months).

18. Walk The Freedom Trail

Boston in winter offers a unique opportunity to walk the Freedom Trail with fewer crowds. The 2.5-mile trail takes you through 16 historical sites, offering a glimpse into America’s past. While it may be chilly, a winter walk along this route offers a quieter, more reflective experience.

Many of the sites, like the Massachusetts State House , Paul Revere’s House , and the Old North Church , are just as captivating in winter. Some of them have indoor areas where you can escape the cold for a bit while learning about the American Revolution and Boston’s role in it.

To enjoy the Freedom Trail in winter, it’s essential to dress warmly. Layering is key, as are waterproof boots, gloves, and a hat. Boston winters can be quite cold, with temperatures often dropping below freezing, especially in the evenings. I recommend insulated snow boots that are easy to walk in and a puffer coat, or at the very least a heavy wool coat with layers. But make sure to check the weather before you go: Boston in the winter fluctuates like crazy!

You can do the trail yourself since it’s pretty easy, but you won’t get much info about the history of the buildings. If you’re a history buff, I recommend doing a guided tour , which in my mind is worth it, but then again I’m obsessed with Boston History!

Check out some of the top tours here.

17. Go Museum Hopping

Boston is home to a wide range of museums that cater to all kinds of interests, from art and history to science and technology. If you’re looking to engage in a cultural exploration of the city, museum hopping is a great way to do it. Here’s a brief rundown of some must-visit museums and what you can expect at each.

Museum of Fine Arts (MFA)

What to Expect : The MFA is one of the largest and most comprehensive art museums in the U.S. It boasts an extensive collection that spans multiple continents and centuries, from Ancient Egypt to modern American art.

Details : Located in the Fenway-Kenmore neighborhood, it’s accessible via the Green Line’s Museum of Fine Arts stop. General admission is $25 for adults, but there are discounts for seniors, students, and youth.

Isabella Stewart Gardner Museum

What to Expect : This museum offers a unique blend of art, architecture, and horticulture. The Venetian-style palace surrounds a beautiful courtyard garden.

Details : It’s a short walk from the MFA, so you can easily visit both in one day. Admission is $20 for adults, and if your name happens to be Isabella, you get in for free!

The New England Aquarium

What to Expect : This is a must-visit for marine life enthusiasts. Highlights include a giant ocean tank, a penguin exhibit, and a variety of hands-on activities.

Details : Located on the Central Wharf, it’s easily accessible from the Blue Line’s Aquarium station. Tickets are around $32 for adults and $23 for children.

Museum of Science

What to Expect : A perfect destination for families or anyone interested in science and technology. The museum offers interactive exhibits on topics like physics, biology, and astronomy.

Details : Situated near the Charles River, you can get there via the Green Line’s Science Park/West End station. General admission starts at $29 for adults and $24 for children.

The USS Constitution Museum

What to Expect : This maritime museum offers an in-depth look at the history of the USS Constitution, the world’s oldest commissioned naval vessel still afloat.

Details : Located in the Charlestown Navy Yard, it’s a bit of a trek but worth it for history buffs. Admission is by donation, so you pay what you can.

The Institute of Contemporary Art (ICA)

What to Expect : If modern art is more your style, the ICA is the place to go. The museum features rotating exhibits of contemporary artists and offers stunning harbor views.

Details : Situated in the Seaport District, it’s accessible via the Silver Line’s Courthouse station. Admission is $15 for adults, and free for everyone on Thursdays from 5 to 9 p.m.

Boston Children’s Museum

What to Expect : This is an ideal spot if you’re museum-hopping with younger kids. The museum is designed to be interactive and educational, with exhibits on everything from science and culture to environmental awareness.

Details : Located on Children’s Wharf along Fort Point Channel, it’s close to the Red Line’s South Station. Admission is $18 per person, but they offer $1 admission every Friday from 5 to 9 p.m.

16. Winter Food Tour

When it comes to experiencing Boston in winter, food is an essential part of the journey. The city’s culinary scene offers a blend of traditional New England fare and innovative cuisine that can warm you up on the coldest winter days. Here’s how to go on a winter food tour in Boston, featuring some iconic foods and where to find them.

New England Clam Chowder

What to Expect : A creamy, hearty soup filled with clams, potatoes, and onions. It’s a quintessential comfort food for Boston in winter.

Where to Go : Legal Sea Foods in the Seaport District or Quincy Market is a popular choice for an authentic bowl of clam chowder.

Lobster Roll

What to Expect : Fresh lobster meat served in a grilled, buttered roll. It’s a luxurious treat that’s delicious year-round.

Where to Go : Neptune Oyster in the North End is well-known for its high-quality lobster rolls, albeit at a premium price.

Boston Cream Pie

What to Expect : A two-layer sponge cake filled with cream and topped with chocolate glaze. It’s so iconic, it’s the official dessert of Massachusetts.

Where to Go : The Omni Parker House in Downtown Boston is where this dessert was invented, so it’s a must-visit for the real deal.

Baked Beans

What to Expect : Navy beans slow-cooked with molasses and pork. It’s an old-school dish that’s rich in flavor and history.

Where to Go : Durgin-Park in Faneuil Hall used to be the go-to, but since it’s closed, you can head to places like Union Oyster House for a traditional take on this dish.

What to Expect : A crispy pastry tube filled with sweet ricotta cheese, often garnished with chocolate chips or pistachios.

Where to Go : Mike’s Pastry or Modern Pastry in the North End are both famous for their cannolis and usually have lines out the door, even in winter.

Roast Beef Sandwich

What to Expect : Thinly sliced roast beef piled high on an onion roll, usually accompanied by BBQ sauce, mayonnaise, and cheese.

Where to Go : Kelly’s Roast Beef in Revere Beach is an institution for this local favorite.

Sam Adams Beer

What to Expect : While not a food, no trip to Boston is complete without trying a locally brewed Sam Adams.

Where to Go : The Sam Adams Brewery in Jamaica Plain offers tours and tastings, perfect for warming up on a cold winter day.

If you want to get going on your food tour earlier in the day, then try out a classic Boston brunch . There are tons of breakfast spots in Boston and this is a huge event during weekend winter days!

15. Harbor Cruise

Believe it or not, harbor cruises aren’t just for summer. Some operators offer winter wildlife cruises, a unique way to experience Boston in winter. You’ll have the opportunity to see seals, sea birds, and the breathtaking skyline, all while bundled up and sipping hot tea or coffee.

Several companies offer a variety of harbor cruises , even during winter. Whether you’re interested in history, sightseeing, or just enjoying the sea air, there’s likely a cruise for you. Some popular options include:

• Sunset Cruises : Catch the early winter sunset over the harbor.
• Historical Cruises : Learn about Boston’s maritime history.
• Dinner Cruises : Enjoy a meal as you take in the city skyline.

Most of the winter cruises leave from Long Wharf or Rowes Wharf, both of which are easily accessible via public transportation. If you’re driving, parking is available but can be pricey.

During the holiday season, some companies offer special-themed cruises, such as New Year’s Eve cruises with fireworks or Valentine’s Day cruises for couples. These tend to sell out quickly, so booking well in advance is recommended.

14. Visit the Boston Tea Party Ships & Museum

The Boston Tea Party Ships & Museum is not your typical museum experience. You’ll have the opportunity to participate in reenactments, explore authentically restored tea ships, and even throw replica tea crates into the harbor just like the Sons of Liberty did back in 1773.

The museum has a series of exhibits and interactive displays that offer insights into the events, people, and ramifications of the Boston Tea Party. One highlight is the “Eleanor,” one of the museum’s restored ships where you can experience firsthand what it was like to be part of the protest.

The museum is located on Congress Street Bridge in Boston, just a short walk from the South Station, making it easily accessible via subway, bus, or even a leisurely stroll if you’re already downtown.

While the museum is indoors, the ship exhibits can get chilly in winter, so dress warmly. But the wintertime also tends to be less crowded, so you can explore at a more relaxed pace.

Adult tickets are around $30, and discounts are available for children, seniors, and military personnel . Operating hours can vary by season, so it’s best to check the official website for the most current information.

13. Brewery Hopping

Boston isn’t just famous for its historic sites and seafood; it’s also a burgeoning hub for craft beer enthusiasts. Brewery hopping is an excellent way to get a feel for the local scene, and doing it in winter gives you an excuse to sample some of the darker, richer brews that pair well with chilly weather.

Boston breweries offer a wide range of beers, from hoppy IPAs to robust stouts. In winter, you’ll find seasonal offerings with flavors like cinnamon, ginger, and chocolate. Many breweries also have indoor taprooms and even fire pits to help you shake off the cold.

Samuel Adams Brewery

What It’s Known For : Being one of the pioneers of the American craft beer movement.

Winter Specials : Look out for winter lagers and seasonal ales.

Location : The brewery is located in Jamaica Plain, and they offer tours and tastings.

Harpoon Brewery

What It’s Known For : Their flagship Harpoon IPA and a wide variety of other styles.

Winter Specials : Try their Winter Warmer, a spiced ale that’s perfect for the season.

Location : Located in the Seaport District, they also have a beer hall where you can pair a fresh pretzel with your brew.

Trillium Brewing Company

What It’s Known For : Innovative, high-quality beers, including hop-forward and experimental brews.

Winter Specials : Seasonal stouts and barrel-aged offerings.

Location : They have multiple locations, but the Fort Point location is a popular choice.

Dorchester Brewing Company

What It’s Known For : A focus on traditional styles, as well as some fun experimental brews.

Winter Specials : Expect darker, richer brews during winter.

Location : Located in Dorchester, this brewery also has a spacious taproom.

Night Shift Brewing

What It’s Known For : A wide range of unique and flavorful beers.

Winter Specials : They often release special brews during the holiday season.

Location : Their taproom is in Everett, a short drive from downtown Boston.

12. Beacon Hill Exploration

Beacon Hill , with its gas-lit streets and Federal-style row houses, is one of Boston’s most iconic neighborhoods. Exploring it in winter adds a layer of charm that makes it feel like you’ve stepped into a real-life snow globe.

In winter, the snow adds a picture-perfect touch, especially in the evenings when the gas lamps are lit. You’ll feel like you’ve stepped back in time.

Start your exploration with a visit to the Massachusetts State House , recognizable by its gleaming golden dome. While the exterior is impressive in its own right, the interior is open to the public and offers historical and architectural intrigue.

One of the most photographed streets in the U.S., Acorn Street is particularly enchanting in winter. The cobblestones and historic homes take on a magical quality when dusted with snow.

This is Beacon Hill’s main thoroughfare, filled with boutique shops, cafes, and antique stores. It’s a great place to grab a hot chocolate or a warm meal. In winter, many of the shops have festive window displays.

Lastly, Beacon Hill is adjacent to Boston Common , the oldest public park in the U.S. In winter, the park is transformed into a winter wonderland, complete with ice skating at Frog Pond.

11. Attend a Boston Pops Concert

When it comes to cultural experiences in Boston, attending a Boston Pops concert ranks high on the list. The Pops are renowned for their blend of classical music and popular tunes, and there’s no better time to experience their magic than during the winter season, especially around the holidays.

The Boston Pops Orchestra , usually just called the “Pops,” is famous for making orchestral music accessible to the general public. In winter, their repertoire often includes holiday classics, traditional pieces, and even some contemporary hits. It’s not uncommon to hear Tchaikovsky’s “Nutcracker Suite” one moment and a jazzy rendition of a holiday pop song the next.

Conducted in the historic Symphony Hall , decorated to the hilt with festive ornaments and lights, the atmosphere is nothing short of magical. The Holiday Pops concerts often feature sing-alongs, special guest appearances, and even a visit from Santa Claus.

Located in Boston’s Back Bay area, Symphony Hall is considered one of the world’s best concert halls, acclaimed for its superb acoustics. The grand interior, with its intricate moldings and chandeliers, adds a sense of occasion to any concert. This is one of the must-see shows in Boston during winter!

10. Hot Chocolate Tour

What’s better than hot chocolate in winter? Not much! Boston has several cafes known for their delicious hot cocoa. Take a self-guided tour or just visit a few places to find your favorite hot chocolate in Boston in winter. Some of my personal favorite spots include:

L.A. Burdick Chocolate

What It’s Known For : Their “Drinking Chocolate” is made from shavings of real chocolate rather than cocoa powder.

Location : Located in the heart of Harvard Square in Cambridge, it’s easily accessible via the Red Line.

Tip : This place is often busy, especially on weekends, but the wait is worth it.

Flour Bakery + Cafe

What It’s Known For : A traditional hot chocolate that hits all the right notes—rich, creamy, and perfectly sweet.

Location : They have multiple locations, but the one in the South End is particularly cozy.

Tip : Pair your hot chocolate with one of their mouth-watering pastries.

What It’s Known For : Italian-style hot chocolate, which is on the thicker side and can be customized with flavored syrups.

Location : Multiple locations throughout Boston, including Back Bay and Downtown Crossing.

Tip : Opt for the whipped cream on top; you won’t regret it.

Tatte Bakery & Café

What It’s Known For : Offering a decadent “Nutella Hot Chocolate.”

Location : With locations in Beacon Hill and Kendall Square among others, it’s easy to incorporate into your Boston itinerary.

Tip : This spot is also known for its pastries, so consider a combo for the ultimate treat in a French-style cafe.

Thinking Cup

What It’s Known For : Their Valrhona Hot Chocolate is made from Valrhona chocolate and steamed milk.

Location : Conveniently situated along the Freedom Trail, near Boston Common.

Tip : This café also specializes in coffee, so it’s a good option if your group is split between coffee and hot chocolate lovers.

Max Brenner

What It’s Known For : A chocolate-focused restaurant offering an entire menu of hot chocolate variations.

Location : Located in the Back Bay area.

Tip : Try their “Mexican Spicy Hot Chocolate” for something a little different.

9. Boston Winter Village

This seasonal pop-up features a mix of shopping, dining, and entertainment, all designed to celebrate Boston in winter. Think of it as a winter fair with a variety of activities, from ice maze explorations to shopping for winter apparel.

Imagine twinkling lights, holiday decorations, and the buzz of holiday shoppers all set to the soundtrack of classic winter songs. That’s Boston Winter Village for you. A mix of local artisans, food vendors, and various activities make this a one-stop destination for winter fun.

The village is populated by a variety of kiosks and small pop-up shops, many of which feature local artisans and makers. From handcrafted jewelry to unique Boston souvenirs, there’s a little something for everyone on your gift list. And winter treats are aplenty here. From hot chocolate and mulled wine to food trucks serving up seasonal favorites like roasted chestnuts, the Boston Winter Village is a foodie’s paradise.

One of the highlights is usually an outdoor skating rink. Even if you’re not a skater, it’s fun to watch others take to the ice. Rentals are available, so you don’t have to lug your own skates around the city.

Weekends often feature live entertainment, ranging from local school choirs to professional musicians. The vibe is festive, adding an extra layer of holiday cheer to your visit.

Boston Winter Village is usually set up in a central downtown location, often near City Hall Plaza, making it easily accessible by public transportation. If you’re already downtown for other activities, it’s a convenient stop.

8. Check Out One of Boston’s Famous Speakeasies

Boston has a rich history that stretches back to the days of Prohibition, and its modern-day speakeasies pay homage to this clandestine era. These speakeasies are all the rage in Boston right now, and are super popular (and cozy!) spots in the winter.

What It’s Known For : Despite its simple name, Drink offers a complex cocktail experience with bartenders who are more like mixologists.

Location : Situated in the Fort Point neighborhood, near the Seaport.

Tip : There’s no menu here; you tell the bartender what you like, and they whip up a custom cocktail for you.

Yvonne’s

What It’s Known For : Yvonne’s offers an opulent experience with a modern twist on the classic supper club. The atmosphere is a mix of vintage and trendy, featuring intricate chandeliers and plush seating, making it a stylish take on the speakeasy concept.

Location : Situated in Downtown Crossing, just a short walk from the T station.

Tip : Don’t just stick to drinks; their small plates menu is well worth exploring. The “Grilled Lollipop Lamb Chops” and the “Baked Oysters” are must-tries.

What It’s Known For : This place is famous for its creative cocktails and laid-back atmosphere.

Location : Tucked away in Union Square in Somerville, just a short trip from downtown Boston.

Tip : The entrance is a bit hidden, situated at the back of a hallway behind a café. Look for the door marked “Backbar.”

Wink & Nod

What It’s Known For : A sultry, underground lounge setting with plush seating and mood lighting.

Location : In the South End, accessible via the Orange Line at Back Bay Station.

Tip : They frequently rotate their food menu by hosting different chefs, making each visit unique.

The Hawthorne

What It’s Known For : An upscale speakeasy that feels like someone’s stylish living room, complete with bookshelves and comfy chairs.

Location : In Kenmore Square, easily accessible from the Green Line.

Tip : Their cocktail menu is extensive but don’t skip their small bites, which are just as impressive.

Brick & Mortar

What It’s Known For : This speakeasy focuses on classic cocktails with a modern twist.

Location : Located above Central Kitchen in Cambridge’s Central Square.

Tip : The entrance isn’t obvious; it’s an unmarked door next to a hardware store.

What It’s Known For : Not quite a speakeasy in the traditional sense, but its basement location and vintage vibe give it a hidden-away feel.

Location : Nestled in the downtown area, close to Park Street Station.

Tip : Try their signature comfort foods like mac and cheese.

7. Visit the Public Library

When people think about things to do in Boston in winter, visiting a library might not be the first thing that comes to mind. However, the Boston Public Library is no ordinary library; it’s a historic landmark, an architectural wonder, and a cozy sanctuary all rolled into one.

The Boston Public Library isn’t just a place to read or borrow books. It’s home to stunning architecture, historical collections, rotating exhibits, and even a café . The library offers a tranquil escape from the bustling city outside, making it a perfect spot for a quiet afternoon.

Seriously, if you’re a fan of dark academia , then you’ll want to check out the Boston Public Library simply because it’s gorgeous! Boston is a collegiate historical city and that’s clearly reflected here.

The McKim Building, the older part of the library, is known for its grandeur and Renaissance Revival architecture. When you walk into Bates Hall, you’ll be stunned by the high, coffered ceiling, the rows of green-shaded lamps, and the sense of tranquility that pervades the room.

The modern counterpart to the McKim Building, the Johnson Building is all about contemporary comforts. It’s bright, open, and home to a variety of resources, including computers, an expansive children’s library, and popular fiction and non-fiction titles.

The Boston Public Library’s main branch is located in Copley Square, easily accessible by taking the Green Line to Copley Station.

6. Shop on Newbury Street

If you find yourself in Boston in winter and have a penchant for shopping, you absolutely must stroll down Newbury Street. Known as Boston’s most famous shopping street , Newbury has a little bit of everything—from high-end boutiques to popular chains, vintage stores, and even some cute cafés for when you need a shopping break.

Newbury Street is a shopper’s paradise. It’s home to a variety of retail experiences, ranging from luxury brands like Chanel and Gucci to local boutiques that offer something uniquely Bostonian . You’ll also find home decor shops, bookstores, and plenty of beauty and skincare options.

The atmosphere is part of what makes shopping on Newbury Street so enjoyable. Cobblestone sidewalks, historic brownstones, and trees strung with fairy lights make it a charming place to be, even more so when there’s a blanket of snow on the ground.

All that shopping can make you hungry. Luckily, Newbury Street has an array of food options. Grab a quick bite from a food truck, settle in for some fine dining, or warm up with a hot drink from one of its many cozy cafés.

Even if you’re not a big shopper, I recommend that you walk down Newbury Street and enjoy the atmosphere. This is one of the prettiest spots in Boston in the winter!

5. Take a Tour

Boston is a city rich in history, culture, and stunning sights that can be enjoyed all year round. If you’re visiting Boston in winter, taking a guided tour can provide you with a deeper understanding and appreciation of the city’s many attractions. Here are some of the best tours to consider when you’re in Boston during the colder months:

Freedom Trail Tour

What It Is : A guided tour along the 2.5-mile-long Freedom Trail that takes you through 16 historical sites.

Why It’s Great in Winter : The winter snow adds an extra layer of charm to this historic walk. Just bundle up and maybe grab a hot cocoa beforehand!

Trolley Tour

What It Is : A hop-on, hop-off trolley service that covers Boston’s major attractions.

Why It’s Great in Winter : It’s a quick way to see the sights without spending too much time in the cold. Some even have heated trolleys!

Harbor Cruise

What It Is : A boat tour that gives you fantastic views of the Boston skyline and harbor area.

Why It’s Great in Winter : While many harbor cruises run only in warmer months, some specialty winter cruises offer breathtaking views of the snowy cityscape.

Brewery Tour

What It Is : Visit some of Boston’s best breweries to learn about the beer-making process and sample some local brews.

Why It’s Great in Winter : A brewery tour is an indoor activity, making it perfect for a chilly day. Plus, many breweries offer seasonal winter ales.

Haunted Boston Ghost Tour

What It Is : This evening walking tour takes you through some of Boston’s most haunted sites while telling tales of the city’s eerie past.

Why It’s Great in Winter : The early sunset and chilly weather add to the spooky atmosphere.

Fenway Park Tour

What It Is : A behind-the-scenes tour of Boston’s iconic baseball stadium.

Why It’s Great in Winter : While there’s no baseball in winter, the stadium tour is still available and much less crowded.

Food Tour of the North End

What It Is : Sample some of Boston’s best Italian food as you stroll through its oldest neighborhood .

Why It’s Great in Winter : The hearty Italian fare will warm you up in no time.

4. See the Tree Lightings

One of the most festive activities to do in Boston in winter is attending one of the many tree-lighting ceremonies. The city is home to several grand trees that are illuminated in spectacular fashion. From the ceremony at Boston Common to others in different neighborhoods, it’s a twinkling way to ring in the holiday season.

3. Skiing and Snowboarding

If you’re a winter sports enthusiast, you’ll be thrilled to know that Boston in winter offers relatively easy access to a variety of skiing and snowboarding options. While the city itself doesn’t have ski slopes, there are several excellent resorts and mountains within a couple hours’ drive. Here are some of the best spots to consider:

Wachusett Mountain

Location : About an hour and a half from Boston.

What’s Special : A solid mix of beginner, intermediate, and advanced runs. They also have night skiing, so you can hit the slopes after the sun sets.

Loon Mountain

Location : Around two hours north in New Hampshire.

What’s Special : Known for its expansive terrain and excellent snow conditions. It’s bigger than many of the closer resorts, offering a broader range of trails.

Sunapee Mountain

Location : Also about two hours away, in New Hampshire.

What’s Special : Sunapee is great for families and offers a balanced variety of trails for skiers and snowboarders of all levels.

Blue Hills Ski Area

Location : Just 30 minutes from downtown Boston.

What’s Special : While it’s smaller and has less challenging runs, it’s the closest option for a quick day trip to scratch that skiing itch.

If you’d prefer to go for a weekend, there are plenty of awesome mountains in New Hampshire , Vermont , and Maine that are a few hours’ drive.

2. Go Sledding

When the first big snowfall hits, one of the simplest and most enjoyable winter activities in Boston is sledding. Grab your sled, or even a cafeteria tray if you’re a college student looking for a cheap thrill, and head to one of the city’s many parks that become sledding havens in the winter. Here are some top spots to consider:

Boston Common

Location : Central Boston

What’s Special : This iconic park offers multiple hills suitable for all age groups. The Frog Pond area is a popular sledding spot, offering easy slopes for younger kids.

Larz Anderson Park

Location : Brookline

What’s Special : Known for having one of the largest and steepest hills in the Boston area, it’s perfect for those looking for a little more speed and excitement.

Arnold Arboretum

Location : Jamaica Plain

What’s Special : This park is ideal for sledding among beautiful, snowy trees. The sloping terrain provides plenty of options for sledders of various skill levels.

Prospect Hill Park

Location : Waltham

What’s Special : With multiple hills and an incredible view of the Boston skyline, Prospect Hill offers a sledding experience that’s both fun and scenic.

1. Visit Nearby Small Towns

One of the cool things about being in Boston in winter is that you’re not far from some quintessentially New England small towns that look like they’re straight out of a holiday card. A quick drive can transport you to charming locales where you can experience a different, more relaxed vibe. Here are a few spots worth the trip:

Location : About 30 minutes north of Boston.

What’s Special : Known for its witch trials, Salem offers history, museums, and a charming downtown area. In winter, the crowds are smaller and the vibe is cozier. See the top things to do here , as well as some awesome Salem restaurants here .

Location : Roughly 30 minutes west of Boston.

What’s Special : The town is rich in literary history, being the home of authors like Thoreau and Emerson. Walden Pond is particularly peaceful in the winter months.

Newburyport

Location : About an hour north of Boston.

What’s Special : This coastal town is beautiful in winter. With fewer crowds, you can really enjoy the boutiques and seafood restaurants at a leisurely pace. Plus, Newburyport offers some cozy, historic hotels that you won’t want to leave!

Check out our favorite things to do in Newburyport here , and our top Newburyport restaurants here.

Location : An hour and a half north of Boston.

What’s Special : Known for its art galleries and Bearskin Neck , a scenic stretch of old fishermen’s shanties converted into shops, Rockport offers a serene oceanfront experience in winter with plenty of things to do and delicious restaurants.

FAQs About Visting Boston In Winter:

Just how cold does boston get in the winter.

Boston winters can vary, but they’re generally cold. Temperatures can range from mild to quite chilly. Here’s a general idea:

• Average High: Around 41°F (5°C)
• Average Low: Around 28°F (-2°C)
• Average High: Around 36°F (2°C)
• Average Low: Around 22°F (-5°C)
• Average High: Around 39°F (4°C)
• Average Low: Around 25°F (-3°C)

Snowfall is also common, especially in January and February. The city can receive anywhere from a light dusting to several inches of snow in a single storm.

Wind chill can also be a factor, making it feel colder than the actual temperature. It’s not unusual to have days where the wind chill dips into the single digits or even below zero in Fahrenheit, particularly in January and February.

Basically, Boston in the winter is pretty chilly. It won’t be as cold as, say, Canada, but you  will want to bring tons of layers. Even for a night out at a bar, everyone will be dressed in sweaters.

What should I pack for Boston in the winter?

Boston in winter is chilly, often snowy, and sometimes downright freezing. But that doesn’t mean you have to sacrifice style for warmth. Here’s how you can look chic while braving the Boston cold:

Wool Coat : Go for a classic wool coat that reaches at least down to your thighs. Black, navy, or camel tones are versatile and timeless.

Puffer Jacket : For especially cold days, a sleek puffer jacket can be both warm and stylish. You’ll see a lot of  long puffer coats in Boston, usually in darker colors.

Leather or Suede Boots : Knee-high or ankle boots with a good grip are perfect for navigating the city streets.

Sneakers : A pair of stylish yet functional sneakers can be great for days when you’ll be doing a lot of walking but the weather is dry.

Snow Boots : Of course, you’ll see plenty of snow boots in Boston. I love a good low pair of snow boots that are cute and comfortable.

Sweaters : Pack a variety of knits, from chunky turtlenecks to slim cashmere pullovers. We pretty much wear sweaters everywhere in Boston in the winter, from museums to pubs.

Long-Sleeve Tees : These are great for layering under sweaters and jackets. Stick to neutral colors to maximize outfit combinations.

Accessories

Beanie or Fedora : A cute hat can keep you warm while also upping your style quotient. I personally wear a knit beanie everywhere I go – this is a staple.

Scarf : Go for a large, cozy scarf that can double as a wrap. Plaid or herringbone patterns can add some texture to your look and are pretty common.

Leather Gloves : They’re warmer than you think and way more stylish than chunky knit ones. This is the “upscale chic” city vibe for Boston in winter.

Lastly, you’ll want to bring nice sunglasses and simple jewelry. You’ll see most people wearing leggings or jeans tucked into boots just about everywhere, though you can get away with a tweed skirt and tights if the weather is more mild.

Guys tend to dress pretty casual and preppy, with simple jeans, workboots or snowboots, henleys, puffer coats, or wool coats (when they’re feeling fancy).

Is Boston walkable in the winter?

Boston is definitely a walkable city, even in the winter months. The compact layout of the city makes it convenient to go from one neighborhood to another on foot, and many attractions are clustered close together.

Boston gets its fair share of snow, and while the city is generally good at clearing main roads, you might find some smaller streets and sidewalks that are icy or slushy. Be careful when walking, and it’s advisable to wear boots with good grip.

Also, daylight is limited during winter; the sun sets as early as 4:30 p.m. in the deepest winter months. If you plan to walk around, either make the most of the daylight hours or stick to well-lit areas if you’ll be out in the evening.

Boston’s public transportation system, known as the “T,” is generally reliable and can be a great way to cover longer distances or to give yourself a break from the cold. Just be aware that inclement weather can sometimes cause delays. So plan in about 30 minutes anytime you want to take the T, even if it’s supposedly a short jump (there’s almost  always at least one delay).

While Boston is walkable, it’s worth noting that it’s also an old city with cobblestone streets, which can be a bit tricky to navigate in icy conditions. If you or someone in your group has mobility issues, extra caution will be needed. And you  won’t want to wear heels

Cozy Boston Hotels During The Winter:

When you’re visiting Boston in winter, a cozy hotel can make all the difference. Nothing beats returning to a warm, inviting space after a day of exploring the chilly city. Here are some hotels that offer that extra level of coziness you’ll crave during your winter getaway.

The Liberty Hotel

Location : Beacon Hill What’s Special : Situated in a converted jail, The Liberty offers a unique blend of historical charm and modern luxury. With warm fireplaces in the lobby and plush bedding, it’s a cozy spot to unwind.

Location : Beacon Hill What’s Special : This boutique hotel takes luxury to the next level. Each room features a fireplace, and you’ll have access to complimentary hot chocolate and warm cookies in the lobby.

Boston Harbor Hotel

Location : Waterfront What’s Special : Want to enjoy waterfront views without braving the cold? The Boston Harbor Hotel offers just that. Its rooms are designed to make the most of the views while keeping you snug and warm.

Omni Parker House

Location : Downtown What’s Special : Known as the longest continuously operating hotel in the U.S., Omni Parker House has a rich history and classic New England charm. It’s famous for its Parker House Rolls and Boston Cream Pie.

Location : Back Bay What’s Special : Sustainability meets luxury at The Lenox . The hotel features eco-friendly amenities, but what makes it a winter haven are the real wood-burning fireplaces in some rooms.

So, there you have it—a comprehensive guide to making the most out of Boston in winter. Despite the cold and snow, this historic city has a unique charm that truly comes alive during the winter months. From festive tree lightings and holiday markets to world-class museums and cozy hideaways, Boston offers a multitude of experiences that cater to all kinds of interests.

Visiting Boston in winter lets you see the city in a different light—literally and figuratively. The shorter days make the city lights glow brighter, and the snow-draped architecture turns familiar landmarks into postcard-worthy scenes. Yes, it’s cold, but with the right gear and a hearty New England spirit, you’ll find the city to be just as welcoming in winter as in any other season.

So, if you’re wondering whether to visit Boston in winter, the answer is a resounding yes. With a little preparation and an open mind, you’ll find that Boston’s winter offerings are as rich and rewarding as those of any other season. Get ready to layer up, step out, and dive into a winter wonderland like no other!

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16 Top Things to Do in Boston in Winter

Written by Shandley McMurray Updated Mar 24, 2023

Winter in Boston is no joke. With lows bottoming out at around 19 degrees in January, and highs averaging in the high 30s to mid-40s from December through February, you'll need to pack layers while visiting Boston in winter. Don't let the cold dissuade you from an early year visit. Boston is at its most majestic (not to mention quietest and cheapest) during the most frigid months.

Fans of the white stuff will rejoice while sightseeing around Boston in the winter, especially if they arrive in January or February, when the average snowfall ranges from 12 to 14 inches. The fresh powder is optimal for sledding through Boston Common or snowshoeing at Gore Place . There are so many fun things to do in Boston in winter that you'll almost forget that it's cold.

Hit the city during the Holidays, and you'll be blessed with pretty illuminations at the Museum of Fine Art's Festival of Lights , fun tree lighting ceremonies throughout town, Hanukkah celebrations at Faneuil Hall , and an impressive First Night celebration on New Year's.

Plan your cold weather visit with our list of the best things to do in Boston in winter.

1. Skate or Sled in Boston Common

2. walk the freedom trail, 3. admire the view from the prudential skywalk observatory, 4. explore the museums, 5. drink hot chocolate, 6. tour the taza chocolate factory, 7. watch a play in the theater district, 8. shiver while frostbite sailing in boston harbor, 9. shop 'til you drop at the prudential center, 10. visit a holiday market, 11. cheer for the home team at a celtics or bruins game, 12. take an old town trolley tour, 13. snowshoe at gore place, 14. go curling at boston seaport, 15. curl up with a good book at boston public library, 16. board the mayor's enchanted trolley, map of things to do in boston in winter, boston, ma - climate chart.

Unleash your inner Michelle Kwan (or perhaps just try to make it around a lap without falling) on the Boston Common Frog Pond . Set in the heart of the oldest public park in the country, this beloved pond is home to a skating school, and offers skate rentals, including seal-shaped aids to help little ones (or wobbly adults) find their balance.

Once you're well and truly chilled, or tired from landing so many triple axels, head to the Frog Pond Café for some warm and hearty comfort food and hot chocolate. The rink is open from November through March, and skating on it is one of the best things to do in Boston in winter.

If you're lucky enough to visit during a snowfall, grab a sled or a cafeteria tray and head to Flagstaff Hill . This is one of the best-known sledding destinations in the city.

While a smattering of snow might make it hard to spot the 2.5-mile-long red-brick line marking the Freedom Trail in winter, it's still one of the best places to visit in Boston. This long, winding path passes 16 of the city's most important historic sites, including the Massachusetts State House , Old South Meeting House , Old State House , and the site of the Boston Massacre .

The path also leads to Faneuil Hall , home of an iconic marketplace worthy of a few hours at least. From shopping to eating to watching a dance show or concert, there are so many fun ways to pass the time at this historic locale. Plus, Quincy Market is just next door.

The most incredible view of Boston can be found at the Prudential Skywalk Observatory. The best time to visit is during the late afternoon, when you can watch the sunset alight the sky with pink and orange hues.

Set on the 50 th floor of the Prudential Building , the Skywalk Observatory is one of the top tourist attractions in Boston . Visiting during the winter rewards travelers with an impeccable, 360-degree view of the snowcapped brownstones, powder-laden streets, frozen Charles River , and whitewashed Boston Common. On a clear day, you can see as far as 80 miles away.

Inside, you'll stay nice and toasty while learning about the city's history through interesting and interactive exhibits.

Good news for those looking for an inside activity. Boston is home to some of the country's oldest (and some would say best) museums. The Boston Tea Party Ships & Museum is unmissable, and easily one of the best places to visit in Boston in winter.

This iconic, floating spot offers visitors an impressive way to step back in time to 1773. Actors roam the recreated tea ships to help educate and entertain visitors who will all get a chance to throw "tea" overboard. Insider's tip: Visit on December 16 th to catch the annual tea party reenactment.

The Museum of Fine Arts Boston is another top attraction in Boston. Here, visitors can gape at masterpieces in every genre, ranging from ancient Egyptian sculptures to intriguing photography to modern street art. Insider's tip: celebrate Diwali at the ancient festival of lights in mid-November.

Treat the kids to a day at the Boston Children's Museum . Explore bubbles in the Science Playground, create something awesome in the Art Lab, or visit a Japanese silk merchant's home.

There's no better drink to warm your chilled bones than a sweet cup of hot chocolate. From sickly sweet to spicy to vegan, winter travelers will be rewarded with a wide variety of hot chocolate options to tickle their taste buds. Here are our favorite spots:

Tucked away on Clarendon Street, L.A. Burdick Chocolates is tiny yet beautiful, and boy does it smell great! Be prepared to meet many others here while sampling the creamy chocolates and the yummiest hot chocolate around. Insider's tip: the vegan dark is just as good as the milk. Grab a bag to bring home.

While Thinking Cup is best known for its coffee, you'd be amiss to avoid sampling its French hot chocolate. Rich and creamy, it's made with 64 percent Tainori Valhorna drinking chocolate. Insider's tip: there are three locations to choose from: Boston Common, the North End, and Back Bay.

1369 Coffee House has two locations: Inman Square and Central Square . That's a good thing since its offerings are both unique and unmissable. Ever had Mexican hot chocolate? Its spicy blend of coriander and cinnamon will awaken your senses, while the Dutch Homemade Hot Chocolate is a sumptuous gift to your mouth. Technically in Cambridge, it's a short, 15-minute (or less) commute.

Face it, there's no such thing as too much chocolate. That's why we had to add a tour of the Taza Chocolate Factory to our list of the best things to do in Boston in winter. You're welcome!

Technically in Sommerville (a 14-minute drive from Boston Common), this top attraction is a must-see (and taste). Famed for their stone-ground chocolate, Taza offers tours every Monday through Sunday to introduce visitors to their intricate treat-making process. It includes samples!

Insider's tips: Kids will love you forever if you take them to Taza Cacao Scout Bingo or Chocolate Story Time on a weekend morning. Be sure to book in advance, as the spots fill up almost as quickly as your belly will.

It's impossible to leave here empty-handed, so expect to be tempted into purchasing anything from the entire Chocolate Mexicano collection to a few bags of the delectable sea salt and almond dark bark.

Boston's main theater district consists of over a dozen venues set in the downtown core. Whether you're looking to attend a Broadway musical, Christmas-themed performance, or dance show, you'll find it all (and so much more) in this glitzy area.

Even if you aren't a fan of opera, you should visit the iconic Boston Opera House . A Washington Street staple, this lovely Baroque building is an example of luxury at its best. During the months of November and December, this is where you'll find The Nutcracker ballet, a holiday season must-see, especially for those traveling with kids.

Don't miss a trip to the Colonial Theatre on Boylston Street. Recently revamped in an extravagant (and very costly) renovation, the building's innards are intriguingly ornate. This is also where many popular shows have premiered before moving on to New York's Broadway.

Only hardcore sailors would be willing to rip through the frigid waters of Boston Harbor between November and April. Apparently, there are a ton of people willing to do just that. If you're one of them, bundle up and head to the Boston Sailing Center in Lewis Warf or Winthrop Frostbite Sailing Club in Winthrop (near Boston's Logan airport).

In addition to the exhilaration you'll feel as the frosty breeze hits your cheeks, you'll be rewarded with an unbeatable view of the city. A sailing newbie? No worries. You can take lessons at the sailing center, but you'll want to bundle up.

Not willing to risk falling in (or getting frostbite)? Check out the sailing centers' websites to find race times, and head to the harbor to watch from the dry shore with a cup of something hot and steamy to warm your hands.

Whether you're looking for holiday gifts or hoping to spend the day in a cozy, indoor spot, Prudential Center (called "The Pru" by locals) won't let you down. They've got all the big names, like Saks Fifth Avenue , Ann Taylor , Canada Goose , Lululemon , L'Occitane , and Sephora . You can even buy a Peloton bike or an armful of books from Barnes and Noble .

When it's time to eat, get your nosh on at one of the many tasty restaurants. Our faves include: Wagamama for noodles (their juices and dumplings are divine) and Sweet Green for a healthy break (the crispy rice bowl is delish). Eataly offers visitors a three-floor Italian dining and shopping experience.

What's the holiday season without a market? Held annually at the City Plaza Government Center , the Boston Winter Holiday Market is one of the most popular events in Boston, attracting close to 100,000 visitors each year. It opens the day before Thanksgiving and runs through New Year's Eve, offering visitors an ideal place to find the most unique holiday gifts.

The market's eclectic shops are housed in adorable European-looking "chalets," and you'll find a ton of tasty treats to fill your belly, as well as a wide range of festive shows and other entertainment to up the fun factor at this top winter attraction in Boston.

Love markets and craft fairs? Old South Church (in Copley Square ) hosts an annual Christmas Fair in early December. It's worth a visit just to ogle at the building's gorgeous architecture.

The South Boston Holiday Market is another one-day wonder held in early December at the Ben Franklin Institute . You'll be hard-pressed to find more innovative food, jewelry, and clothing designs than those on offer at this unique spot.

It's easy to get excited while watching a game at the TD Garden . The official home of basketball legends the Boston Celtics (they've won 17 NBA Finals) and hockey champs the Boston Bruins , this popular sports and entertainment venue is the largest of its kind in New England, and catching a game is one of the best things to do in Boston in winter.

Visited by more than 3.5 million people annually, the venue boasts over 200 events a year, so you might also be able to catch a concert while you're in town. Grab a bite at one of the Garden's three private restaurants or settle in to enjoy the game with Cheetos popcorn, nachos, burgers, or fries at one of the on-site concessions stands.

Walking through slushy streets can get annoying after a while. Take a break while still seeing the sights with a ride on the Old Town Trolley. Prepare to spend at least 100 minutes riding around town, listening to the guide's fantastic stories as he or she narrates your journey through the city's best spots.

Hop off at one of the 19 stops to enjoy the restaurants, shopping, or historic sites up close. Then, hop back on when you're ready to travel to the next destination. No need to futz around with parking or navigate around snowbanks, let the trolley driver do the hard work while you sit back, relax, and soak up the heat.

Technically outside Boston, Gore Place sits a mere nine miles from the downtown core. This country estate, which spans 50 acres, boasts a historic mansion and a farm so close to the city, you'll forget you aren't there. Each winter, Gore Place allows visitors to practice a pastime many of us have yet to experience: snowshoeing.

For a small fee ($20 for adults and $10 for kids aged 6 to 12), adventure seekers can strap on a pair of snowshoes and trek atop the fluffy white stuff as they explore the vast grounds. No snowshoes? No problem! As long as the ground is covered in snow, you can rent them (for adults and kids) from the Carriage House .

Gore Place isn't the only snowshoe-worthy spot. Strap 'em on and head to the Esplanade , Boston Common , or the Weston Ski Track for more outdoor adventures.

Snowport may well be the best thing to come to Boston Seaport, one of the city's hippest neighborhoods. You'll find it sandwiched between the waterfront and the historic Fort Point district , waiting to wow you with its fun (and sometimes free) activities.

In addition to iceless curling, this winter wonderland is jam packed with fun events the whole family will enjoy. Twirl around the 3,000-square-foot ice rink, munch on a baked waffle, or take a yoga class.

Didn't bring skates? No problem. You can rent them on-site, along with skating aids for less confident skaters. Not a fan of waiting your turn? Curling, which is offered for free, is open to reservations, so you can be guaranteed a slot when you arrive.

If you're looking for historic charm coupled with the intoxicating smell of old books, head to the Boston Public Library. Located on Boylston Street, a six-minute walk from Prudential Tower, the Central Library consists of two buildings located in Copley Square .

The historic McKim Building , which opened in 1895, was designed by architect Charles Follen McKim. Inside, you'll find the rich interiors and elegant touches you've read about, and a charm so inviting, you'll want to curl up at one of the desks with a good book.

The Bates Hall Reading Room is unmissable. Its emerald green desk lamps are almost as captivating as the ornate domed ceiling, intricate windows, and stone balcony.

The more contemporary, Boylston Street Building was opened in 1972 and designed by Philip Johnson. In 2016, it underwent a renovation, making this an uber modern space featuring impressive perks like a broadcasting studio.

Each December, the Mayor boards the Enchanted Trolley for a tour of the city. He spends a weekend (including Friday) aboard the festively adorned trolley, visiting the various neighborhoods throughout town and stopping at multiple spots to participate in tree-lighting ceremonies.

Join the fun festive activities, which include carol singing, holiday performances, and a visit (or more) with Santa. You can find out where the trolley will be and when online.

Looking for more bright lights? Check out Boston's First Night celebration , held every New Year's Eve to ring in the new year in style. You'll see fireworks, concerts, and other fun performances.

More Related Articles on PlanetWare.com

Unmissable Destinations in Massachusetts: The state of Massachusetts has so many great things to offer. From adorable small towns with storied pasts to sandy dune-lined beaches along Cape Cod , you will fall in love with these best places to visit .

Other Places to Visit in Winter : In addition to scoring the best deals on hotels, heading to cold locations boasts a bevy of other bonuses (we're looking at you, Christmas markets and ski resorts). Begin with a look at our list of the best winter vacations in the U.S for ideas. In Canada, check out these fun things to do in Vancouver in Winter . Or, for a little more adventure, head to one of these top winter holiday destinations around the world that are packed with snow!

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Backpacking in the USA , Winter Travel

Boston in winter: the ultimate guide .

I visited Boston many years ago, just for a day trip, so following the success of the guest post about Free Things to do in Boston, I asked Tegan and Alex from Why Not Walk to share their top tips for visiting Boston in Winter and they certainly came through!  Check out their ultimate guide to visiting Boston in winter:  

Boston is the capital of Massachusetts and is one of the oldest municipalities in the United States.  Famous for its history, whale watching tours and delicious food, Boston is a wonderful city to visit at any time of year, but here is why you should visit Boston in winter to make the most of the special winter activities and events.

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Know Before You Go to Boston

Before travelling to Boston, make sure you book accommodation and popular attractions ASAP as hotels and tickets can sell out.

🛌 MY FAVOURITE ACCOMMODATION IN BOSTON:

$$ The Revolution Hotel : creatively designed rooms great for groups

$$ The Verb Hotel : a music-themed boutique hotel near Fenway Park

$ HI Boston Hostel : a modern hostel with private and dorm rooms

⭐ TOP 3 BOSTON ACTIVITIES TO BOOK IN ADVANCE:

1. Guided Walking Tour of the Freedom Trail

2. Boston Tea Party Ships and Museum Interactive Tour

3. Boston Fenway Park: Guided Ballpark Tour

Find Deals to Book Your Trip

Flight Deals

Hotel Deals

Group Tours

Winter Weather in Boston

Many dismiss Boston as too cold in the winter for a visit, picturing howling winds and icy roads. However, given that Boston is a coastal city, its proximity to the Atlantic Ocean truly gives it the best of both worlds: it’s much more temperate than the rest of the state and region in the wintertime, but still gets to enjoy several gorgeous, fluffy snowfalls each year.

That said, average winter temperatures in Boston hover around or just below freezing, with January typically being the coldest month.  January also usually gets the most snow, although you can expect some snow from November through to April.

Why Visit Boston in Winter?

Boston is bursting with fun things to do all year, but we would argue the wintertime is an extra special time to visit.  Stroll along romantic cobblestone streets, stop for a hot chocolate or perhaps some outdoor ice skating, and enjoy Boston’s wealth of museums, local breweries, charming neighborhoods, sports teams, and more.

Read on for all our best tips for the ultimate winter visit to Boston, and for more Boston tips for any time of year, check out Why Not Walk’s Boston-area landing page here .

What to Wear in Winter in Boston

Layers, layers, layers! We cannot stress this enough. While Boston’s temperatures aren’t quite as cold as people like to think they are, what we do have in spades here is wind. The downtown and Seaport areas, in particular, are known for wind tunnels that can get fairly brutal due to their tall buildings, so we definitely recommend a scarf and gloves, as well as a jacket with a hood or a beanie or hat.

As Boston is a walking-heavy city, you should definitely bring warm and comfortable shoes, preferably waterproof ones. We especially recommend boots (like Uggs or Timberlands) and of course some nice, thick socks. 

As for a coat, down or alternative down is the way to go. You’ll see many Bostonians rocking the knee- or ankle-length coats. This isn’t totally necessary if you usually live in warmer climes, but definitely make sure to bundle up, and plan a mix of indoor and outdoor excursions for each day. 

YOU MAY ALSO LIKE: Free Things to do in Boston Massachusetts

Things to Do in Boston in the Winter

You could live in Boston for years (like we have) and still not experience everything Boston has to offer. Boston has something for everyone, from the history aficionado to the sports fanatic to the autumnal leaf-peeper.

Here are some of the top things to do in Boston at any time of year: 

• Boston’s “Little Italy” North End Pizza & History Walking Tour
• Boston History & Highlights Walking Tour
• Day Trip Tour to Quincy and Plymouth
• Boston Duck Boat Tour with Cruise Along Charles River
• Guided Walking Tour of Harvard University Campus

You can browse more tours and attractions in Boston here, or enjoy some of the best free things to do in Boston . While you’re visiting Boston, plan an epic East Coast road trip , as well!

FIND A TOUR IN BOSTON

While visitors flock to Boston and the region in the fall to see autumn foliage , we’d argue that a beautiful snowfall gives the leaves a run for their money. If a winter “city break” is what you’re after, Boston will not disappoint. Keep reading for all the best tips on the best things to do in Boston in winter, the city’s top winter attractions, and a sample Boston 2 day itinerary. 

Recreate the Boston Tea Party

Yes, it’s probably the most touristy thing to do in Boston, but if it’s your first time in the city then learning about the famous Tea Party at the interactive museum is a fun way to forget the weather!  This ships and museum tour runs several times a week even in the winter and allows you to travel back in time to 1773 to be part of the famous Boston Tea Party and the events leading up to the American Revolution.

You can explore fully restored replicas of the Tea Party ships, take part in an interactive museum tour and re-live the events of the day with live actors and 3D holograms.  You’ll even have the chance to throw your own tea overboard! 

Money Saving Tip

Visit the museums in boston.

Wondering what to do in Boston when it snows?  When the weather is poor, getting inside and visiting some of Boston’s incredible museums is a great way to keep warm and dry and learn something at the same time!

The Museum of Fine Arts (Back Bay/Fenway) houses over 450,000 works of art at the world’s 17th-largest museum. 

The Isabella Stewart Gardner (near the MFA): Once the home of notable Bostonian Isabella Stuart Gardner, the house and artwork were turned into a museum under the terms of her will. The ISG gained notoriety for a 1990 art heist that remains unsolved to this day. Don’t miss the gorgeous courtyard in the center.

The Boston Science Museum (Lechmere): though a bit dated, science fans will enjoy the Science Museum’s many exhibits and indoor zoo.

The Museum of African American History (Downtown): Don’t miss a visit to New England’s largest museum dedicated to preserving and honoring African-American history, located in the African Meeting House– the oldest Black church building in the U.S.

The Institute of Contemporary Art (Seaport): If modern and contemporary art is more your scene, the ICA does not disappoint. It also has lovely views of the Harbor area, and its neat architecture is an exhibit unto itself.

Check Out Vintage Movies, Glamorous Shows and Improv Comedy

These are some of our favorite places for a more unique Boston experience, especially during the winter!

Watch vintage movies (often in 35mm!) at Brattle Theatre (Harvard Square) or the Coolidge Corner Theatre (Brookline.) Coolidge Corner is the oldest Art Deco theatre in the area, built in 1933.

Get dressed up for a show at the Boch Center or the Emerson Colonial Theatre . You will be awe-struck at the beautiful decor, sweeping ceilings, and enormous chandeliers. All 3 of these theatres opened in the early 1900s and are some of the oldest continuously operating theatres in the region. You can also enjoy Boston’s premier symphonic ensembles at the Boston Symphony Orchestra (Fenway.)

Alternatively, laugh ‘til your sides hurt at a comedy show at ImprovAsylum (North End.)   

Warm Up with Hot Chocolate

Any excuse for a tasty hot chocolate is fine by me, and these tasty treats will warm you right up on a cold Boston winter day!

The Mexican hot chocolate at Ogawa Coffee House is absolutely decadent, and its location in downtown Boston is perfect if you’ve just gone ice skating at the Frog Pond (more info on that below!)

Located in the swanky Back Bay, LA Burdick offers all sorts of artisanal chocolate offerings, including hot chocolate.

If you don’t want to choose just one, check out seasonal Hot Chocolate Flights at The Met Back Bay . You can even ask for yours to be spiked!

If you like to combine your cocoa with Christmas carols, this cruise on Boston Harbor takes in the beautiful sights of the Boston Skyline while listening to Christmas music and carols as you sip on your cocoa. 

Bonus: If hot chocolate isn’t for you, and you’re more in the mood for normal chocolate, check out the Chocolate Factory Tour at Taza in Somerville.

YOU MAY ALSO LIKE: Things to do in Orlando in Winter

Ice Skating and Winter Sports in Boston

The ultimate Boston winter experience is outdoor ice skating at the Boston Common Frog Pond . The Common is the “Central Park of Boston,” and is located in the heart of downtown. Tip: if you go after sundown, there are twinkly lights all over the park that really set the scene! There is also seasonal ice skating at City Hall Plaza ’s Boston Winter installation, as well.

If indoor ice skating is more your scene, check out the Steriti Ice Rink in the North End. Admission is free, and you can rent skates for a few dollars. Pair this with a visit to the North End (Boston’s Italian neighborhood) and Boston Harbor afterwards. 

If you don’t want to splurge on (very pricey) hockey tickets, you can watch the Boston Bruins practice at Warrior Ice Arena. 

Enjoy the Red Sox stadium tour without the crowds– it’s available year-round!

If you are interested in attending sporting event while you are in town, check out the TD Garden calendar for Bruins and Celtics tickets, as well as concerts! 

Brewery + Distillery Tours

What better way to warm up on a wintery day in Boston than with a tasting of your favorite tipple?  You could join a tour that takes in three of the top breweries in town , or check out our recommendations below:

Sam Adams (Jamaica Plain): Sam Adams is definitely touristy, but worth a visit if you’re visiting Boston for the first time, or if you’re interested in how one of the nation’s largest breweries operates. The tour is free (make sure to reserve ahead of time), and you get samples and a free small glass with your tour. Sam Adams recently opened a new taproom in the Faneuil Hall area as well. 

Harpoon Beer Hall (Seaport): Harpoon wins “best brewery tour” in our book, hands down. Harpoon is a super fun atmosphere– they’re employee-owned, make amazing pretzels with their leftover beer byproduct, and their beer hall in the Seaport can’t be beat. Definitely sign up for their brewery tour– it costs $5, but includes some time at the end for unlimited samples! 

Boston Harbor Distillery (Dorchester): Their table-side tasting tour offers several samples and a history of their operation for $20/pp. They also have a VIP tour ($50/pp), offering a “back-room of whiskey-making” experience. Also in Dorchester is Bully Boy Distillers , which is worth a look too.

You should also check out these beer and brewery tours that are guaranteed to keep you warm and tipsy!

Explore Beautiful Wintry Neighborhoods in Boston

There are some lovely neighborhoods in Boston where you can talk a stroll, no matter what the weather.  Just wrap up warm and enjoy!

Beacon Hill

Located right behind the Boston Common with Charles Street as its main drag, don’t miss a visit to Beacon Hill while in Boston. Characterized by its cobblestones and mix of Victorian- and Federal-style brick row houses and antique black streetlamps, Beacon Hill is so charming and picturesque – and quintessentially Boston.

Don’t miss the State House with its gold dome, especially beautiful when covered in snow, and Acorn Street, one of the U.S.’s most-photographed streets.  

Likely Boston’s most “fancy” neighborhood, Back Bay is also home to beautiful architecture, as well as a large shopping district including Newbury Street and the sparkly Prudential Center. The Commonwealth Avenue Mall, leading up to the Public Garden, is beautiful in any season.

Boston’s Italian district is also Boston’s first neighborhood, continuously inhabited since 1640. The North End is adorned with narrow, winding streets and some of Boston’s oldest surviving architecture. Don’t miss American Revolution hero Paul Revere’s house and the infamous Old North Church (of “one if by land, two if by sea notoriety), both on the Freedom Trail.

Places to Check out Snow in Boston

If snow is what you’re after, you have a good chance of seeing it between December and March, with January and February usually clocking in as the coldest and greyest months with the most chance for that sort of precipitation. There is sometimes snowfall as late as April, to the delight of visitors and chagrin of locals.

Top Tip: If you want to increase your chances of seeing snow, plan a quick day trip to Western Massachusetts and the Berkshires while you’re in Boston, as they have fairly constant snow cover and are only about 2 hours away.

Closer by, the towns surrounding Boston are excellent places to enjoy a fresh snowfall – Brookline and Chestnut Hill, in particular, have beautiful Victorian architecture and stately homes that make a gorgeous backdrop for photos, and their wonderful reservoirs and parks are at their most impressive when covered in snow. 

Holidays in Boston

Boston really gets into the swing of the holiday spirit during the winter, check out the variety of holiday-themed pop-ups at bars around the city, including the Tiki bar Christmas pop-up at Shore Leave (South End), Pop-up igloos at the Envoy Hotel (Seaport) and a Hanukkah-themed pop-up at Backbar (Somerville).  You can even get your fix of Holiday movie-themed cocktails at Precinct Kitchen & Bar (Back Bay)!

Christmas in Boston

Holiday and Christmas lights appear all around the city during the winter.  The Boston Common is festooned with twinkling lights, as well as a lighting ceremony for a huge Christmas tree. Visit Faneuil Hall downtown, to see Quincy Market decorated with lights and decorations, and book tickets to see the Nutcracker ballet at the Boston Opera House.  

New Year’s Eve in Boston

First Night Boston is the city’s biggest New Year’s Eve celebration.  It is family-friendly and alcohol-free so if you are visiting Boston with kids then they will love it!  There are fireworks over Boston Common at 7pm, and another spectacular display over Boston Harbor at midnight. 

You can watch a parade, admire ice sculptures, watch a pyrotechnic show and catch some live music performances.  It is one of the best things to do in Boston in December, and a wonderful way to welcome in the New Year.  This website has more details about the events.

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How to Spend Winter in Boston 2 Day Itinerary

If you need some more tips for things to do in Boston during the winter, this Boston itinerary has more suggestions for you! 

Boston in Winter Itinerary Day 1

Start your day in Copley Square, visiting its churches and the Boston Public Library , and exploring the Back Bay neighborhood.

Tip: the BPL is one of Boston’s best-kept secrets. Built in 1888, its interior is absolutely gorgeous. Don’t miss the 2nd floor Bates Room for old-school study vibes, or the outdoor courtyard in the middle (follow the signs on the ground floor.)

Meander along Newbury Street, perhaps stopping in one of its chic eateries for brunch as you walk along. Newbury Street also has Boston’s most upscale shopping, if that’s in your budget. Pop over a block to the Commonwealth Avenue Mall promenade for a snowy stroll.

Continue down to the Prudential Center, a shiny shopping center where you can thaw for a little bit on a chilly day. For a lovely Italian market experience, check out Eataly. 

If you’re in the mood for some seafood for lunch, check out Saltie Girl . If that’s a bit out of your budget, enjoy locally-sourced DIY bowls at Dig Inn .

In the afternoon, take the green line or a ride-share a few stops to the Fenway area to visit the Fenway Baseball Stadium, the Museum of Fine Arts, and the Isabella Stuart Gardner Museum. If you’re not feeling too cold, the Fens area of the interconnected parks known as the Emerald Necklace is lovely in the winter.

In the evening, check out the South End for trendy eateries and bars. Stop into the Beehive for a drink and live jazz music, or Barcelona Wine Bar . If you decide to stay in the Copley area, Lolita is another favorite, for frozen margaritas and other cocktails in what we like to call a “dungeon-glamour” locale.

Lastly, a favorite bar in Seaport is Drink , for really neat DIY cocktails. Here’s how it works: you sit down at the bar, tell the bartender what combination of flavors and liquors you like (e.g. vodka and citrus, or “drinks that don’t taste like alcohol,” or rum and bitter), and they make you a surprise. It could be a bartender invention or an obscure combination – you never know!

Boston in Winter Itinerary Day 2

In the morning, take the MBTA’s green line or a ride-share to the Boston Common to start the Freedom Trail : a 2.5 mile walking tour of Boston’s esteemed role in the history of the United States. Pair the Freedom Trail with its sister tour in Beacon Hill, the Black Heritage Trail .

For a full, step-by-step guide to both trails (plus bonus local content!), check out Why Not Walk’s definitive guide to the Freedom Trail . We recommend allotting at least a half day for the Freedom Trail. While it can theoretically be done in about 1.5 hours, you will definitely want to spend longer at various sites!

The Freedom Trail ends in Charlestown, at the Bunker Hill Monument and the USS Constitution. You can spend some time exploring the area, or make your way back downtown for lunch.

For quick bites downtown, check out Sam LaGrassa’s for sandwiches, Dig Inn for locally-sourced bowls (if you didn’t go to the Back Bay location yesterday!), or Clover Food Lab for vegetarian-friendly fare. In nearby Chinatown, there are delicious dim sum and dumpling restaurants galore. One particular favorite is Gourmet Dumpling House .

Alternatively, there is something for everyone at Faneuil Hall Marketplace, which is a stop along the Freedom Trail if you’d like to take a break then. Here, you can sample Boston’s famous lobster rolls (we recommend hot rolls more than cold!) drizzled with fresh butter or clam chowder in a bread bowl. Note: For a less-touristy place to try lobster rolls, there’s always Yankee Lobster in Seaport.

In the afternoon, tour the North End, Boston’s quintessential Italian neighborhood. We hope you saved some room from lunch, because you can’t miss sampling hand-made Italian cookies, cannoli, gelato, and other treats here. Don’t miss the epic Mike’s Pastry versus Modern Pastry cannoli battle, at the very least.

You can stay in the North End for dinner too, choosing one of many restaurants (you can’t go wrong!) such as Regina’s for pizza, or Trattoria Monica , Giacomo’s , or Antico Forno for pasta and other Italian fare. Note that Giacomo’s does not take reservations, so you will likely have to start lining up at around 3PM or earlier to get in for dinner. This may not be worth it if you’re on a tight schedule.

In the evening, enjoy the downtown Boston bar scene at classy Yvonne’s or the Marliave , or the really fun dive bar Biddy Early’s . Watch live Irish music with the Guinness on tap flowing at Black Rose . If breweries are more your scene, check out Harpoon or Trillium in the Seaport, Dorchester Brewing Company in Dorchester, or Lamplighter in Cambridge.

Where to Stay in Boston This Winter

After a long day of exploring Boston, Massachusetts, you’re going to need somewhere to rest your head and get energized for the next day.

Here are a few great options for hostels and hotels in Boston for your visit:

HI Boston Hostel : This modern, environmentally friendly hostel is near Boston Common, Chinatown, the subway and most of the city’s sights. Dorms feature individual lockers and personal shelves, reading lights, and power outlets. You’ll get lots of privacy balanced with common spaces for socializing when you stay here. >>>CHECK PRICES

The Verb Hotel : A small, music-themed boutique hotel near historic Fenway Park. Fans of rock ‘n roll will love the funky decor and party atmosphere. Plus, it’s literal steps from some of Boston’s best restaurants, shopping, and activities. >>>CHECK PRICES

The Godfrey Hotel Boston : Stylish, sophisticated, and centrally located, this hotel provides excellent access to just about everything a guest would want to do in Boston.  >>>CHECK PRICES

If you’d like more options, you can browse all hostels in Boston on Hostelworld , or find great value hotels on Booking . There are also various options for Airbnbs in Boston too, take a look at some of the rental homes available here .

BROWSE HOTELS IN BOSTON

Travel Tips for Boston

We hope this post has inspired you to book your winter vacation in Boston this year!  Be sure to check out these extra travel tips to help you plan the best trip to Boston you can:

Getting There

• Use Skyscanner to find cheap flights to your destination.
• Public buses are the cheapest ways to get to your accommodation from the airport, but a shared shuttle transfer is quicker and cheaper than a taxi - you can pre-book those on GetYourGuide or Viator
• Try Omio for booking trains and Busbud for buses including Greyhound and Flixbus.

Where to Stay

• For hotels, I use Booking.com to check reviews and find the best deals on hotels and apartments wherever I'm travelling to.  Hotels.com is another good site.
• If you're on a tight budget, use Hostelworld to find the best hostels all over the world

• Get a quote for car hire with Discover Cars who compare car rental deals from many companies so that you can choose which is best for your trip.

Book Tours and Activities

• I use GetYourGuide or Viator to book everything from skip-the-line entry tickets to food tours as I can compare options from several companies and choose the best one for me
• If you're staying in a hostel, check out their tours and activities which are usually free or very cheap - and a great way to meet people!  

Get Travel Insurance

• Unfortunately, things can and do go wrong when you travel.  I never leave home without travel insurance, so consider getting insurance for your trip to cover things like adventure sports and activities as well as emergency medical, lost luggage, stolen items, trip cancellation and more.  
• Get a quote for your trip from True Traveller if you're based in the UK, or World Nomads or SafetyWing which both offer travel insurance for backpackers and long-term travellers.  Alternatively, use a comparison site like Travel Insurance Master to find the best cover for you.

Check Your Travel Documents

• Don't forget to check the validity of your passport and any other documents for your trip.  Use iVisa to check if you need a visa to visit your destination, and get up to date official travel advice from your government, for example on the Department of State website in the US or the UK government website .

Get Cheap Currency

• When travelling abroad, using a travel bank account like Wise means you get great deals on foreign currency - including a fee-free transfer of up to £500 when you use this link to sign up . 

Top Money Saving Tip for Backpackers

• Work exchanges are a great way to travel for longer and extend your trip as you can save a ton of money on accommodation.  Get an extra $10 discount on Worldpackers here or learn more about work exchanges .

About the Authors

Tegan George & Alex McKenzie

Tegan and Alex are travel, hiking, and biking enthusiasts currently based in Boston, USA. There is nothing they love more than exploring new places by walking, and they have visited over 30 countries together since they met in 2015. Their love for “walking the world” led them to found Why Not Walk , a travel guides site. Follow them on Instagram , Facebook , or Pinterest to start planning your next adventure.

If you’re looking for travel insurance for your trip to Boston, get a quote now from World Nomads .

Like this post?  Pin it to read later:

Just to let you know, this post may contain paid or affiliate links, which help to maintain Tales of a Backpacker and give me the chance to keep travelling, and to keep creating awesome content for you!  I only recommend goods and services I believe are useful and reliable.

Hi! I'm Claire Sturzaker, a 30-something foodie traveller who loves to enjoy the best of a destination without breaking the bank. I'm here to help you and all women backpackers to plan their best budget travel adventure. I am an avid supporter of female solo travel, and took my first solo trip 20 years ago! I love to write about travel, hostels, backpacking and van life.

1 thoughts on “ Boston in Winter: The Ultimate Guide  ”

Nice post Tegan and Alex. Super comprehensive guide here. Well done. I am heading to Middleton in under 2 weeks for a month long trip, about. We will miss Boston during winter but may take a trip into town as we will be about 30 minutes outside of Beantown.

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A local’s guide to surviving (and thriving) in a Boston winter

Feb 14, 2024 • 7 min read

Boston in winter? Totally worth it. Venture out into the icy air or retreat inside to cozy cafes and fireside tables, with food and drink to warm you from the inside out © Kimberly Maroon/Lonely Planet

Sponsored by

Bostonians don’t let the weather stop us, even in the coldest months. This is New England, after all, so we know how to make the most of winter. Join us as we venture out into the icy air or retreat inside to cozy cafes and fireside tables, with food and drink to warm you from the inside out.  

Embrace your inner winter warrior

Sometimes the best way to survive winter is to embrace it – don your warmest coats, hats and gloves, go outside, and play! Boston offers plenty of opportunities to do so, even right downtown at the Boston Common , where there’s sledding on Flagstaff Hill and ice skating on the Frog Pond. But locals know the hills in the outer neighborhoods are even more exciting, such as at the Sugar Bowl in Jamaica Plain, Walsh playground in Dorchester, and Fallon Field in Roslindale. Escape the crowds on the Frog Pond by heading to The Rink at 401 Park, in Fenway, or Skate @ Canal District, in Kendall Square in Cambridge.

You don’t have to venture too far out of the city for more adventurous snowy ski action. West of Boston, Weston Ski Center in Weston and Great Brook Farm in Carlisle both offer picturesque countryside, groomed trails, and equipment rental for cross-country skiing. For downhill, the Blue Hills Ski Area is just 15 miles south, in Canton.

If you prefer your winter sports at slower speeds, head to Harbor Way in the Seaport District to try your hand at curling. Don’t worry, it’s a lot more fun to do it than to watch it on TV! For less action and more relaxation, do winter the Nordic way with a visit to Moki Sauna Village on the Rose Kennedy Greenway. This outdoor wellness center offers wood-fired saunas and refreshing plunge pools for the ultimate winter warmup.

No matter what your winter recreation, you’re fortunately never far from a rich and rewarding cup of hot chocolate. Bostonians go cuckoo for cocoa, especially for the French hot chocolate at the Thinking Cup (in the Back Bay, the North End and Downtown) and for the dark hot chocolate at LA Burdick (in Harvard Square and in the Back Bay). For extra oomph, cozy up inside Caffé Vittoria in the North End for hot chocolate spiked with Kahlúa and brandy.

Escape the winter chill

If all these outdoor activities are making you shiver, never fear. Boston offers an endless array of indoor attractions for those who prefer to escape rather than embrace the cold. Candlepin Bowling is a classic New England pastime – a regional variation on ten-pin that uses cylindrical pins and smaller balls. Try it at Sacco’s Bowl Haven in Somerville, and follow up with fabulous pizza and craft beers from Flatbread Pizza. Missing your favorite summertime activities? Visit PuttShack in the Seaport District to play a round of mini-golf, or PKL in South Boston to battle it out on the pickleball courts. Both have full-service bars serving craft cocktails and draft beers – and you don’t have to go outside to earn them.

All that activity aside, when the temperatures drop, sometimes you just want to snuggle up with a good book. If that’s the case for you, go directly to Beacon Hill Books & Café. Every exquisitely decorated room of this neighborhood bookstore offers a thoughtful selection of titles to peruse – and plenty of nooks and crannies in which to hunker down and enjoy them. The café’s afternoon tea service will warm up your Sunday.

If you’re still longing for the tropics, Boston has a solution for that, too. The New England Aquarium transports you straight to the Amazon rainforest, the Indo-Pacific coral reef, and other warm-weather destinations. Best of all, the centerpiece Giant Ocean Tank showcases the creatures of the Caribbean Sea. (Pay no attention to those penguins you pass on the way there.)

Arts & culture

Boston is a fabulous destination for the arts year-round – but locals know winter is prime time, as the cultural calendar is packed. In 2024, Boston is hosting an exhibit of `Winteractive’ public art (through April), with 16 playful and poignant installations scattered around the streets of Downtown. Download a map – or just wander and discover.

If you prefer your art indoors, any of Boston’s world-class art museums is an inviting destination on a chilly day. The Isabella Stewart Gardner Museum is a particular favorite for locals, who relish the blooms and greenery in the interior courtyard of this Venetian-style palazzo in Fenway. During the winter months, the garden features glorious tropical plants, including many exotic varieties of orchids.

The performing arts calendar is in full swing all winter, with live jazz and blues heating things up at Wally’s Café and at the Beehive, both in the South End. The Boston Symphony Orchestra and the Boston Ballet both prepare special seasonal programs – this year, the BSO will present Music of the Midnight Sun, a celebration of Nordic composers and artists, and the Boston Ballet’s Winter Experience features three sensuous and soulful ballets by Mikko Nissinen and Helen Pickett.

Eat, drink, and be merry

Nothing warms the body and soothes the soul like a hearty meal. A highlight of any trip to Boston is its seafood – in winter, keep it simple with a hot bowl of creamy clam chowder, especially from Sail Loft in the North End or Row 34 in the Seaport.

Another culinary treat is Boston’s globe-spanning international fare. Every weekend from January to March, the Boston Food & Wine Festival plays host to dinners, classes, and exquisite food and wine pairings from around the world. But you don’t need a festival to tuck into a plate of pasta from Arya Trattoria or Carmelina’s in the North End, or to feast on dim sum at Hei La Moon or Empire Garden in Chinatown. Comfort Kitchen in Dorchester is a beloved local option, serving not-so-local fare from the African diaspora all over the world.

Winter is the perfect time to get cozy with your dinner date next to a roaring fire. Book a table downstairs at the South End Buttery or upstairs at Tresca in the North End. Or for Boston’s most romantic and sumptuous setting, request the firelit library at Yvonne’s. For more casual fireside drinks, sample the mead at medieval-themed Grendel’s Den in Harvard Square; or brush up on your history in Charlestown, where folks have been patronizing the Warren Tavern since 1780.

If you appreciate fresh air (really fresh), several venues keep their outside game going all winter. In South Boston, the Lodge at Publico converts the atrium into a seasonal `ski lodge,’ offering all the amenities of après-ski (if not the slopes). Think flannel blankets, fire pits, and artificial snow, as well as special seasonal cocktails. Fire tables keep patrons warm in the year-round beer garden at Charlie’s Kitchen in Harvard Square and in the courtyard at Bow Market in Somerville. And in the Seaport, the Lookout Rooftop Bar features heated igloos for your outdoor drinking pleasure. Wrapped in clear, weather-proof plastic, it’s a perfect (warm) place to sip a cocktail and admire the views of the sparkling city skyline on a crisp winter night.

Still planning when to book your winter visit? Consider coming for an only-in-Boston holiday. For the first time, the Lunar New Year is an official city holiday, observed on February 10; but the Chinese community will welcome the Year of the Dragon with its festive parade and `cultural village’ in Chinatown on February 18. The following month, March 17 is Evacuation Day, an official holiday commemorating the departure of British troops from the city of Boston in 1776. Of course, this date is better known as St Patrick’s Day – marked by the historic (and now inclusive!) dual-purpose parade in South Boston.

Sponsored by Meet Boston

As a travel entertainment and inspirational media outlet, we sometimes incorporate brand sponsors into our efforts. This activity is clearly labeled across our platforms.

This story was crafted collaboratively between Meet Boston and Lonely Planet. Both parties provided research and curated content to produce this story. We disclose when information isn’t ours.

With sponsored content, both Lonely Planet and our brand partners have specific responsibilities:

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Determines the concept, provides briefing, research material, and may provide feedback.

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We provide expertise, firsthand insights, and verify with third-party sources when needed.

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Visiting Boston in Winter

If you've always wanted to visit Boston but have heard that it's pretty cold in the winter...well, that's true.

But that's no reason to cross Boston off your bucket list of places to see in America.

Just do what we do -- grab a warm coat, a hat, and a scarf, then go out and take in all that the city has to offer.

One good reason to visit Boston in the winter is that there are things to do that you can't do at any other time of the year, like ice skating!

Another bonus is that other than around the holidays, it's off-peak tourist season so there are deals on airfares, train tickets, and hotels.

• Top Boston Winter Activities
• Family-Friendly Winter Attractions
• Christmas in Boston
• Free Things to Do in Boston
• Boston Bus Tours
• Things to Do Year-Round in Boston

Top Boston Attractions For Winter

These top activities include historic sites, outdoor fun, entertainment options, free things to do, and things to do during the holidays.

As you'll see, there is plenty to see and do in and around the city of Boston in the wintertime.

You might want to take a look at these posts, depending on when you are visiting:

• Things to Do in December ( weather )
• Things to Do in January ( weather )
• Things to Do in February  ( weather )

Go Ice Skating

Winter means it's time to put on our skates and hit the ice rinks.

There are some awesome rinks around the city.

Our favorite is the rink on Boston Common Frog Pond.

On a nice day, you can also stroll through the Boston Common which is the oldest public park in the United States, established in 1634.

A few other locations to go ice skating within Boston are:

• Steriti Memorial Rink
• DCR Kelly Outdoor Rink
• DCR Murphy Memorial Skating Rink
• The Rink at 401 Park (AKA Fenway Rink)

Others include:

• Community Ice Skate @ Canal District Kendall | Cambridge
• Simoni Skating Rink | Cambridge
• Kirrance Rink at Larz Anderson Park | Brookline
• Winter Skate at Patriot Place | Foxborough
• Warner Ice Arena | Brighton

For opening dates, hours, skate rental information, ticket pricing, and more, read our full post on Boston Ice Skating Rinks .

Note: for great sledding hills, check out Flagstaff Hill in Boston Common or Larz Anderson Park in Brookline.

Take a Free Walking Tour

Winter doesn't stop our guides from showing you the town!

On one of our  pay-what-you-wish  Boston walking tours , you'll find that groups are smaller so your guide can give some more personal attention!

Try one of these tours:

• Freedom Trail
• Harvard & Cambridge
• Beacon Hill Crime Stories
• North End / Little Italy

We also offer several  self-guided tours  and  GPS-enabled tours  for those who want to explore at their own pace.

Visit Faneuil Hall

If temperatures are colder than you'd like, there's plenty to do at Faneuil Hall to keep you busy and warm!

This historic Boston site features a visitor's center, the Great Hall, and a free military museum.

You can also spend time shopping in a few of the historic buildings that make up Faneuil Hall: North Market and South Market.

There are also plenty of places to fill yourself in a third building, Quincy Market, where you'll find hardy fare such as lobster rolls and chowder (otherwise known as chowda) and many other food options.

In late November there's an annual Christmas tree lighting of a tree that is always magically decorated.

Read more about what to do at Faneuil Hall .

See The Holiday Lights

The holiday season is especially fun in Boston. Hot chocolate never tastes as good as it does this time of year.

Take it from us: as local tour guides, we love feeling the Christmas joy in our city.

We think that you'll love seeing the holiday lights, and our self-guided tour takes you to them!

The tour starts at Faneuil Hall’s Holiday Tree and its fabulous light and sound show.

Then you'll head to Macy’s for the jovial window displays.

The tour also takes you past Boston’s official Christmas Tree and lights on Boston Common, the Commonwealth Avenue spectacular.

Here's the entire self-guided holiday lights tour .

Go to Boston Bruins Game or Other Sports Event

When it's cold outside, it's often nice to get indoors and see a game. Of course, if you want to see a team play outdoors, you can do that too.

Whether you enjoy basketball, football, or hockey, Boston will have a game for you.

• Boston Bruins
• Harvard Crimson
• Boston College Eagles
• Boston Celtics
• New England Patriots

Sports lovers may want to visit the New England Sports Museum .

The museum consists of a half-mile of exhibits at the TD Garden, the home of the Boston Bruins and Boston Celtics.

Tour the USS Constitution

The USS Constitution was one of six ships constructed in accordance with the Naval Act 1794.

The ship was made famous during the War of 1812 as it never lost a military engagement with the British.

Enemy cannonballs made barely made a dent in the ship, earning it the nickname “Old Ironsides”.

The hours are Tuesday to Sunday, 10 am-6 pm. There is a suggested donation, but any amount is appreciated.

Read more about the USS Constitution Museum and Ship Tour .

If you enjoy learning about historical ships, a short walk through the North End from the USS Constitution is the Boston Tea Party Ships and Museum. Find information here about an interactive tour .

Stop By a Holiday Market

Get in the festive mood by visiting a Boston holiday market.

They are a great place to find a unique gift for Christmas or Hanukkah, hand-crafted goods, and delicious foods.

You're sure to find caroling, workshops, and even iceless curling at some of them!

Here are some of the best 2023 markets:

• SoWa Winter Festival and Holiday Marke t | November 24th - December 17th
• Downtown Boston Holiday Market | November 24th-December 23rd
• Faneuil Hall Women's Holiday Market | December 1st-3rd, 8th-10th, 15th-17th, 21st-22rd
• Harvard Square Holiday Market | December 15th-17th & December 21st-23rd
• Snowport Holiday Market | November 10th - December 31st

See a Musical or Play

Warm up your heart with a Boston musical or play in the Theater District.

Check out this list of  Boston theater productions to find tickets for shows you can see when you're in town.

For example, the Nutcracker ballet, a holiday favorite, will be playing in November and December.

You can also check the calendars of these popular venues:

• Charles Playhouse
• Cutler Majestic Theater
• Citizen's Bank Opera House
• Emerson Colonial Theater
• Orpheum Theatre

TIP : If you are on a budget, there are usually at least one or two off- Broadway productions happening at any given time.

Take a Brewery Tour

As an alternative to hot chocolate, stay warm with a pint of freshly brewed beer!

The Samuel Adams Brewery Tour is free though a $2 donation is requested for their charity efforts.

Only guests over 21 will be able to sample, however. The tour takes just under an hour and happens daily except Sundays.

For just $5, you can take a 30-minute tour of the Harpoon Brewery . The tours are one hour and include a sample for guests over 21.

Please note that the entire Beer Hall, including tours, is 21+ only on Saturdays. Tours take place daily.

Ring in the New Year

If you are in town on December 31, you are in for a treat!

The biggest free public celebration is called  First Night Boston .

Ring in the New Year with a spectacular fireworks show that will take place at midnight.

In 2023, the schedule is as follows:

• 12:00 pm | Family Festival Kick-Off. Artistic performances, ice sculpture viewing, and live entertainment continues through midnight.
• 12:00 pm – 4:30 pm | First Night Boston Playhouse . Live performances within City Hall and other nearby indoor and outdoor venues.
• 6:00 pm | First Night Parade . A short “parade” of cultural performances and other guests in downtown Boston.
• 7:00 pm | Family Fireworks On Boston Common
• 8:00 pm | First Night Party On The Plaza . Back-to-back musical performances, ice sculptures, and non-stop light displays.
• ice sculptures, and non-stop lighting displays.
• 11:50 pm | Midnight Countdown
• Midnight | First Night Harbor Fireworks

Visit a Historic Attraction

Any time of the year is a fine time to visit these sites of significant American history events.

Tickets are $10 or less and several don't charge anything for children under 5.

Old North Church

Established in 1723 as Christ Church in the City of Boston, Old North Church is the oldest church building in the city.

It is both a national historic landmark and an active Episcopal Church congregation.

It is open Tuesday – Saturday from 11 am – 5 pm and Sunday from 12:30 pm – 5 pm. Check the site for holiday hours.

General admission tickets are $5 per person. Children under 6 are free. Tours are offered.

Other historic sites:

Paul Revere House

Learn about the midnight ride's famous rider, Paul Revere. It is open 10 am - 4:15 pm, November 1st - April 14th.

Adults: $6 / Children 5-17: $1 / Under 5: Free.

Old South Meeting House

See where the Boston Tea Party got started. This historic colonial landmark is open 10 am - 5 pm.

Adults: $15 / Seniors (62+) & Students: $14.00 / Children (under 12): $8.00

Trinity Church

This is one of the 10 most important buildings in American architecture. See why on a guided tour Tuesday-Sunday 10 am - 5 pm.

Adults: $10 / Seniors and Students: $8.00 / Children under 12: Free.

Old State House Museum

The Birthplace of the American Revolution in Boston is at the Old State House Museum.

It is open from 10 am to 5 pm. Visit the website for a list of planned closures .

Adults $15.00 /Seniors (age 65+) & Students: $14:00 / Children ages 6-12 $8

Save Money With a Tourist Pass

If you’re planning to enjoy a lot of different activities while you’re in Boston this December,  a tourist pass can save you  a lot of money on popular attractions.

One of the easiest options is a build-your-own-pass, which allows you to save 20% off 2 or more tickets. 

Another nice thing about these passes is that they make it easier to save a few bucks on attractions that are already inexpensive.

Here are a few of the most notable tours and tickets included with Boston tourist passes:

• New England Aquarium
• Hop-on-Hop-off Bus Tour
• Boston Duck Tour
• Six Flags New England
• Boston Children’s Museum
• Whale Watching
• Franklin Park Zoo
• Sam Adams Brewery Tour
• Fenway Park Tour

Some of these services also include skip-the-line entry at certain locations, making it easy to save both time and money.

Depending on how you use these passes, you could save anywhere from 20% - 50% or more.

For more information on how to save money with these services, make sure to read our full post covering which  Boston tourist pass  offers the best deals.

Go to a Free Museum

Here are a handful of cool Boston museums that are always free to visit.

• USS Constitution Museum
• Waterworks Museum
• Commonwealth Museum
• Boston University Art Galleries
• Boston Fire Museum
• Boston Athenaeum
• Ancient & Honorable Artillery Company
• Bunker Hill Museum
• Warren Anatomical Museum
• The Russel Museum
• Massachusetts Historical Society
• McMullen Museum of Art
• MIT List Visual Arts Center
• Boston Public Library

These museums are free at certain times:

• Children’s Museum (only $1 on Sunday from 1:30-4:00)
• Museum of Fine Arts (free on Wednesdays from 4-9 pm.)
• Institute of Contemporary Art (Free Thursdays from 5-9 pm)
• Isabella Stewart Gardner Museum (Free on your birthday or if your name is Isabella!)
• Coit Observatory ( Free on Wednesdays nights)

See a list of all the free museums in Boston .

See Gingerbread Houses

The Back Bay neighborhood has an annual gingerbread design competition, each year with a new theme.

All entries can be viewed from December 7th to 21st, 2023, in the Atlantic Wharf Lobby.

To see more of the area, take our   Back Bay Tour  which is offered every Tuesday at 10:00 a.m.

Family-Friendly Winter Activities

Many kids love winter. Above, we've covered some of the things kids can enjoy in Boston like ice skating.

Here are a few more family-friendly things to do. For more ideas, see our post Things to Do with Kids in Boston any time of the year.

Experience Zoo Lights

This holiday display will be up at Stone Zoo until January 7th, 2024, giving families one last opportunity to enjoy the attraction.

Visitors can expect to see live reindeer, decorated animal areas, and a plethora of trees and other displays lighting up the night.

Tickets for this event are separate from tickets to the zoo, but they are also cheaper than zoo tickets.

Learn more about Zoo Lights .

See a Holiday Show

Kids and adults alike love the Grinch and Charlie Brown. If you are in Boston from early December until teh end of the month, you are in luck!

These time-tested classics are in and around Boston this year!

• How the Grinch Stole Christmas  | November 28th-December 3rd| Providence
• Nutcracker  | November 14th-December 13th| Boston
• A Charlie Brown Christmas  | December 16th | Lowell
• Disney on Ice Into the Magic  | December 21st-30th | Boston

Museum of Science

This science museum also has a zoo! It is home to the Hayden Planetarium.

The exhibits range from space discovery to natural science to the physics of sport.

It is open 9 am-5 pm.

Admission varies as there are many add ons such as a visit to the Planetarium or IMAX Theatre.

You can get more information here .

The Commonwealth Museum

Their collection includes John Adams’ expense report from his trip to Philadelphia, John Hancock’s cover letter to the Massachusetts copy of the Declaration of Independence, and more.

With interactive exhibits, The Commonwealth Museum is great for kids.

They can pretend to be a judge at the Salem Witch Trials or figure out if you would be a Tory or Patriot before the Revolution. 

It's free to visit and is open Monday through Friday from 9:00 a.m. - 5 p.m.

Harvard Natural History Museum

The Museum was created to be the “public face” of three Harvard research museums and is a great way to stay warm and explore some of the fascinating exhibits of natural history.

Visitors can touch rock and mineral specimens dating back to the beginning of our solar system and experience glass models of plants, flowers, and more.

Read more about the Harvard Natural History Museum .

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The 15 Best Things to do in Boston in the Winter

There’s nothing like Boston in the winter . And that’s coming from someone who spent two weeks trapped in her freshman-year dorm because the snow was piled higher than the front door.

But it’s also coming from someone who has fond memories of dancing around the Public Garden in her pajamas in the snow after the Patriots won the Super Bowl and who spent many a night strolling through the Boston Common, loving the way the holiday string lights seemed to dance around her.

Winter in Boston can be brutal. But it’s also incredibly magical. I’ve compiled a list of some of the most magical things to do in Boston in the winter, from ice skating on an iconic pond to getting in on the sports culture. Stick to this list, and you’re bound to fall in love with Boston in the winter just as much as I have.

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

15 Fun Things to do in Boston in the Winter

1. go ice skating on frog pond.

When the weather heats up, the Boston Common Frog Pond becomes a place where all the kids play around in the shallow pool, trying to cool off. But when the snowy season starts, Frog Pond becomes one of the best winter activities in Boston. 

Though there are other places to go ice skating in Boston, Frog Pond is likely the most iconic. There are few things better than gliding on the ice with the string lights twinkling on the trees all around you.

2. Join the Beacon Hill Holiday Stroll

If you’re experiencing a Boston winter, visiting Beacon Hill is simply a must-do. As the freshly fallen snow begins to build on the famous cobblestone streets, there’s a certain magic to this historic district.

Beacon Hill also offers one of the best things to do in Boston during winter, the Beacon Hill Holiday Stroll . At the start of December, Charles Street is closed to vehicles, creating an enchanted evening where guests can listen to Victorian carolers, enjoy sampling seasonal treats, and experience some festive fun.

Take the Beacon Hill History Walking Tour

3. Have a Board Game Night at Knight Moves

Over in Brookline, you’ll find a place that’s perfect to spend a cozy night in. Knight Moves is a board game cafe, and having a board game night here is one of the most fun things to do in Boston in the winter.

Grab a comfy sweater, call up your friends, order yourself a hot chocolate, and pick from their vast collection of board game titles. Whatever you’re in the mood for, you’ll find it here. Whether you’re looking for a quest that will take hours to finish or a short game you can play over and over again, the game you want is likely in their collection, which features over 600 titles.

4. Go Tree Lighting Hopping on the Enchanted Trolley Tour

The Mayor’s Enchanted Trolley Tour is a Boston winter tradition that goes back more than two decades. In early December, this tour hops from event to event around the Boston area. 

The mayor’s trolley brings with it tons of holiday fun and signals a time of coming together for the Boston community. In addition to tree lightings happening at stops throughout the tour, there will also be other famous faces alongside the mayor, including Santa and Mrs. Claus.

5. Shop at the Holiday Markets

Need to get some holiday shopping done? Whether you’re looking for gifts or just looking for fun things to do in Boston in the winter, the holiday markets are the place to be.

Several markets pop up in the winter. Over at the Seaport, you’ll find Snowport , which has quickly become one of the biggest markets in the city. Here, you’ll find more than 100 small local merchants, as well as winter-themed games and foods.

Or head to Somerville to experience a litany of events at Bow Market , offering incredible eats and local artisans displaying their wares. Harvard Square also features its own Holiday Fair , which is always bursting with unique finds.

6. Get Tickets to a Hockey Game

Hockey is simply a part of Boston’s culture. Bostonians take great pride in their Boston Bruins , which is why watching a hockey game is one of the best Boston winter activities. 

However, Bruins games can cost a pretty penny. If you want something a little more budget-friendly but just as fun, head to a college game. 

If you want to see something absolutely wild, join the many fans watching the annual Beanpot tournament , which sees the teams from Boston University, Harvard, Boston College, and Northeastern go head to head on two Mondays in the winter, typically the first two Mondays of February. But be warned: These fans fight hard for their school!

7. Spend a Day at the Museums

Boston is filled with many wonderful museums, and spending time exploring them is one of the best things to do in Boston during winter if you want to escape the cold. There’s something for every interest. 

Are you an art lover? The Museum of Fine Arts and the Isabella Stewart Gardner Museum are two top choices.

Meanwhile, science fans will want to find their way over to the Charles River to discover the Museum of Science , which features over 700 interactive exhibits, live presentations, and much more.

If you’re traveling with little ones, you’ll love seeing them expand their imaginations over at the Boston Children’s Museum . 

8. Enjoy the Somerville Illuminations Holiday Lights Tour

If you love when the holiday season starts because of all the beautiful light displays, you’re going to want to head to Somerville for the Illuminations Holiday Lights Tour , one of the best winter activities in Boston. Starting at the beginning of December, this lights tour is actually a month-long show of one of the best and brightest displays around the city.

Although there used to be a trolley tour to help you see all the lights, that is sadly no more due to the cost. But you can still take self-guided tours of the light displays all month long. Plus, there are special events throughout the month, like an evening of city-wide caroling and another night where you can join others to take the tour by bike. 

9. See “The Nutcracker” at the Boston Ballet

From the end of November to the end of December, seeing “ The Nutcracker ” put on by the Boston Ballet at the Citizens Bank Opera House has been one of the best things to do in Boston in the winter for many, many years. 

While the Boston Ballet Orchestra plays Tchaikovsky’s beloved score, the characters are brought to life on stage by the incredible dancers, surrounded by breathtaking sets. It’s a truly enchanting experience, and you’ll want to come back every holiday season to see it.

10. Listen to the Holiday Pops

Speaking of enchanting holiday experiences, the Holiday Pops are another one of the can’t-miss winter activities in Boston. The Holiday Pops are a Boston winter tradition that’s beloved by Bostonians and visitors alike. 

Throughout December, the Boston Symphony Orchestra invites you to Symphony Hall to listen to holiday music favorites and even sing along yourself. Plus, there’s even a visit from Jolly Ol’ Saint Nick himself.

If you have little ones, book a Kids Matinee performance, which includes post-concert pictures with Santa and additional festive treats. There are also special sensory-friendly performances. 

11. Take a Holiday-Themed Harbor Cruise

You might think that a harbor cruise is just a summer activity, but it’s also one of the most fun things to do in Boston in the winter. Come winter, the cruises offer unique options to experience the beautiful Boston harbor in comfort. 

One of the most fun options is the Cocoa and Carols Holiday Cruise , which is put on by Classic Harbor Line Boston. On this cruise, you’ll board a classic yacht that’s all decked out for the holiday season. 

Holiday tunes will play throughout the 1.5-hour-long journey as you enjoy the sights of the Boston skyline. Food and drinks are available to purchase on board, including hot cocoa for the little ones and alcoholic beverages for the grownups. 

12. Head to Harvard for the Midwinter Revels

Each December, Harvard University is home to one of the best things to do in Boston in the winter, the Midwinter Revels . At this unique show, you’ll delight in traditional songs, dances, and stories from cultures all across the world. 

The productions vary from year to year, which is why you should make this show an annual tradition, as you’ll always see something new. 

13. Watch ‘It’s a Wonderful Life’ at The Brattle Theatre

The Brattle Theatre isn’t just any theater. This historic Cambridge institution is known for its movie showcases, which dive into specific movie genres, eras, and directors.

But once the holiday season rolls around, they start up their annual tradition of playing one of the most beloved holiday movies of all time, “ It’s a Wonderful Life .” No matter how many times you’ve seen this film, there’s nothing quite like seeing it in The Brattle’s famous theater. 

14. Go Sledding

Whether you’re a college kid delighted about their classes being canceled or a child who awoke to the joyful sound of the phone ringing to say that school’s off, there’s no better way to celebrate the snowfall than by going sledding. Boston offers plenty of places to enjoy this winter tradition.

The most iconic spot is Flagstaff Hill in the Boston Common. But you’ll also find plenty of fellow sledders at other locations like the Arnold Arboretum and the Sugar Bowl, both in Jamaica Plain.

15. Shop and Eat Around Faneuil Hall

Decorated with beautiful lights and a massive tree for the holiday season, Faneuil Hall is one of the best places to visit in the winter in Boston. This historic area, with its cobblestone streets, is perfectly charming as the weather gets chilly.

Spend some time hopping from shop to shop, from comic book stores to places to get new ornaments for your tree. Then, grab a bowl of clam chowder to warm up and take a seat inside this beloved landmark.  

There you have it! The 15 best things to do in Boston in the winter. What are your favorite winter activities in Boston? Let us know in the comments!

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About the Author:

Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California. When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes. Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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The 15 Best Boston Tours

Get to know one of America's most historic cities with these tours.

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Hoping to experience Boston through the eyes of a local? A guided tour may be just the thing. Factoring in traveler sentiment and expert opinion, U.S. News selected some of Boston's best tours. Whether you're eating your way through the North End or zipping around Boston Common on a Segway, you'll see this New England city in a new light and learn some of its history along the way during these top Boston tours.

The Revolutionary Story Tour

Price: Adults from $76; kids from $38 Duration: 4 hours

Many reviewers call this tour enjoyable and one of the best walking tours they'd ever been on thanks to the engaging guide. Led by a local resident with degrees in history, political science and public policy, the tour takes visitors through the streets of Boston to chronologically retell the story of the American Revolution. Along the 3.5-mile jaunt, you'll pass by a dozen of the sites featured on the Freedom Trail, and you'll also hear about the key players in 18th-century Boston, including John Adams, Benjamin Franklin and Paul Revere.

Tours are offered daily at 9:30 a.m. There is also a 1:30 p.m. tour Thursday through Sunday during the winter months and daily during the summer months through the beginning of November. There is a maximum of 16 people per tour. The company partners with another local guide to provide private tours.

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City Experiences by Hornblower – New England Aquarium Whale Watch Cruise

Price: Adults from $65; kids from $45 Duration: 3.5 hours

Hop on one of City Experience's high-speed catamarans for a whale watching excursion to the Stellwagen Bank National Marine Sanctuary. This area is a magnet for whales, dolphins, sea birds and other marine creatures who head there to feed. New England Aquarium naturalists on board offer their insights on whales, answer questions and explain whale behaviors, a big plus for travelers. During your trip, you may see several different species of whales, including humpbacks, finbacks, minkes, sei whales and endangered right whales.

Tours leave from mid-May through early-November from Long Wharf, which is located near the aquarium. Tour frequency depends on the month, but there is at least one per day. Cruisers say the tour is fun and report seeing plenty of wildlife. Combo tickets that include admission to the aquarium are also available. The company also offers sightseeing and sunset cruises.

CityView Trolley Tours

Price: Adults from $42; kids from $20 Duration: 1 hour

The family-friendly hop-on, hop-off CityView Trolley Tours offer a convenient and comfortable way to explore the city and visit its top attractions , something visitors (especially those in Boston for the first time) appreciate. Stops at the New England Aquarium, Quincy Market and Old North Church, among others, make it easy to access sites along the Freedom Trail and other neighborhoods. What's more, guides share fun and informational tidbits along the way.

Trolleys run daily from mid-April to November from 9:30 a.m. to 4:30 p.m. Note: While you can hop on and hop off the trolley as you please, tickets are only valid for one full tour loop. Two-day passes are also available.

Old Town Trolley Tours – Boston Hop-On Hop-Off Trolley Tour

Price: Adults from $50; kids from $29 Duration: 1.5 hours

Explore the top sights in Boston on this hop-on, hop-off trolley tour that makes 18 stops. Along the route, you can hop off and explore attractions like Faneuil Hall, the "Cheers" bar, the USS Constitution and the Old State House, and then hop back on at your leisure. Without getting off, you'll tour for about 90 minutes. Trolleys frequently stop approximately every 15 minutes. Participants praise the convenience this tour offers and rave about the entertaining, informative guides. Reviewers also say the tour is a great way to see the city without having to do a lot of walking.

Trolleys run daily from 9 a.m. to 4 or 5 p.m., depending on the time of year. For one-day tours, tickets allow for unlimited re-boarding. Tickets also get you discounted rates for a Boston Harbor cruise as well as discounted entry to the Boston Tea Party Ships & Museum. Two-day tickets, as well as the Ghosts & Gravestones evening tour are also available.

Boston Pizza Tours – North End Pizza Tour

Price: From $49 Duration: 2.5 hours

Sink your teeth into some of Boston's best pizza on this walking tour. You'll start your stroll in North End, which is considered Boston's Little Italy. Along the way, you'll pass by five sites on the Freedom Trail, including the Paul Revere House and the Old North Church. The tour cost includes three full-size pizza slices, water and a cannoli. Tourgoers applaud guides for their positive attitudes and entertaining, educational delivery of Boston history. Reviewers are also complimentary of the food.

Tours are generally offered two times daily at 11 a.m. and 2 p.m., but a 5 p.m. tour is offered during certain months of the year. Tours are capped at 12 participants. The tour can accommodate vegetarian diets; those with other dietary restrictions (such as vegan diets or food allergies) will need to take a private tour.

Fenway Park Tours

Price: Adults from $25; kids from $17 Duration: 1 hour

Baseball fans and history buffs relish the chance to take a behind-the-scenes peek at America's oldest ballpark. Even non-baseball fans find the tour worthwhile, according to reviewers. The tour takes visitors to important sites within the ballpark, including the world-famous 37-foot-high Green Monster. The excellent guides, full of Red Sox and Fenway Park trivia, offer an entertaining tour and are a hit with participants.

Tours run year-round from 9.m. to 5 p.m. (at 10 a.m. November through March) and start on the hour. On game days, the last tour is scheduled three hours before game time. Fenway Park also offers a variety of other stadium tours, including Day Game Premium Tours and Fenway in Fifteen, a condensed 15-minute tour.

Courtesy of Rose Kennedy Fitzgerald Greenway

Boston Segway Tours

Price: From $69 Duration: 1 or 2 hours

Boston Segway Tours takes visitors on an adventure through the city. Since it's faster to glide than walk, you can cover much more ground on Segway than by foot. As you travel from Boston Common to the Rose Fitzgerald Kennedy Greenway, your guide takes you by some of Boston's most famous landmarks while always keeping an eye out for riders' safety, according to tour-takers. Pick a two-hour tour to visit Cambridge.

Participants must be 14 or older and weigh at least 100 pounds to ride; additional restrictions may apply.

Urban AdvenTours – City View Bike Tour

Price: From $60 Duration: 3 hours

Exploring Boston by bike is a great way to cover a lot of ground in an exciting, active way. Urban AdvenTours' flagship City View Bike Tour takes participants on a 10- to 12-mile trek through six different neighborhoods. You'll bike through major Boston sites, such as North End, the Boston University campus and Kenmore Square, Fenway Park, the South End, Boston Common and Long Wharf. Along with the comprehensive overview of the city, riders commend the care guides take in making them feel safe.

This tour rides daily at 10 a.m., with additional 2 p.m. departures on Saturday and Sunday during the summer months. The tour is best for those comfortable riding on city streets. Children must be age 10 or older. Adults can upgrade to an electric bike for an additional fee. Urban AdvenTours also offers cycling trips through Cambridge and the Emerald Necklace park system, as well as a family-friendly tour for kids 10 and younger.

Off the Eaten Path Tours

Price: Adults from $95; kids from $40 Duration: 3 hours

On this food tour of the North End – Boston's famous Italian neighborhood – owner Paula Noukos promises more than just samples of tasty food. Besides stopping at popular spots, such as Bricco Panetteria and Galleria Umberto, you'll hear tips on how to shop for the best extra virgin olive oil and balsamic vinegar. You'll also learn about the history and architecture of this unique neighborhood, a highlight for reviewers. Travelers are also fond of the guide and appreciate her vast knowledge of the neighborhood.

Tours are generally offered Tuesday through Saturday at 11 a.m. and are limited to 12 people.

Courtesy of Boston Duck Tours

Boston Duck Tours

Price: Adults from $53; kids from $38 Duration: 80 minutes

Quack and splash your way around Beantown with the entertaining Boston Duck Tours, which takes passengers around Boston and into the Charles River on World War II-style amphibious landing vehicles. On the tour, entertaining "conDUCKtors" keep up a lively patter, describing neighborhoods, Boston history, architecture and trivia along the way. A highlight for many visitors is when the vehicle heads into the river offering a different perspective of the city.

Ticket discounts are available for seniors and children 2 and younger. Tours depart from the Museum of Science, the Prudential Center and the New England Aquarium several times a day from mid-March through early-December.

Boston Crawling – Independence Pub Crawl

Price: From $75 Duration: 2 hours

Sip your way through the city at four historic watering holes on Boston Crawling's Independence Pub Crawl. On this tour, you'll visit pubs that have historic significance, drink local brews and hear Boston's "secret" history as you barhop along the Freedom Trail. Reviewers say the tour is informative and fun and applaud the beer recommendations provided by the guides.

Participants can take tours daily at 3 and 7 p.m. There is also an additional noon tour on the weekends. Tourgoers must be at least 21 years old, regardless of whether they're drinking. Tickets include four draft beers of your choice. If you prefer to purchase drinks as you go, you can purchase tickets for a lesser price.

PhotoWalks Tours of Boston – Freedom Trail

Price: Adults from $45; kids from $20 Duration: 1.5 hours

Explore the historic sites of the city and refine your photography skills at the same time on this tour. In addition to visiting Freedom Trail landmarks, such as Boston Common, Park Street Church, the Granary Burying Ground and the Boston Massacre Site, you'll also learn expert tips on how to use your camera or smartphone to take the best pictures – a highlight for many participants. Reviewers are also complimentary of the insightful guides.

Tours run Tuesday, Thursday and Saturday year-round at 1 p.m. The tour is capped at 10 participants, but maybe more during peak times of the year. If you're interested in exploring other neighborhoods or topics, you can sign up for one of PhotoWalks' other tours, including Beacon Hill and the North End, among others.

Courtesy of the Freedom Trail Tour

Freedom Trail Tours – Walk Into History

Price: Adults from $17; kids from $8 Duration: 1.5 hours

The nonprofit Freedom Trail Foundation leads the way on this tour of the Freedom Trail – a milelong path that weaves past some of the city's most historic sites. A costumed guide, in character, leads you to 11 sites, including Boston Common, King's Chapel, the Old South Meeting House, the Boston Massacre site and Faneuil Hall. Reviewers rave about the guides and the characters they inhabit, and highly recommend this excursion over a self-guided tour of the Freedom Trail.

Tours are given daily at 11 a.m., noon and 1 p.m. Other themed tours, including tours that focus on the women of the Revolutionary War and African American patriots, are also available.

Boston Foodie Tours – Boston Public Market & North End Tour

Price: From $90 Duration: 3 hours

Boston Foodie Tours explores two of Boston's famous mainstays: The North End and the Boston Public Market. After enjoying pizza, cannoli and bread in the North End, you'll wind your way to the market to sample doughnuts and ice cream, among other treats. Your tour concludes with a tasting of clam chowder and cornbread. Past tourgoers say this is a must-do experience while visiting Boston.

Tours run Tuesday through Saturday at 10:30 a.m. and 11:30 a.m. on Sundays. Tours are not given on major holidays. The company also offers a comprehensive tour of the North End, plus a private foodie outing to Beacon Hill, among other options.

City Brew Tours – Boston Signature Brew Tour

Price: From $89 Duration: 3.5 hours

For an in-depth Boston beer education, City Brew Tours' Signature Brew Tour is a great place to start. During the tour, you'll be chauffeured around the city in a comfortable van, visit three craft breweries, get behind-the-scenes tours and enjoy up to 12 different local craft beers and a snack along the way. Tourgoers laud the knowledgeable guides and love that driving isn't an issue.

City Brew offers this tour Wednesday through Sunday. Outings depart at 4:45 p.m. and 5:30 p.m. on Wednesday and Thursday. Friday through Sunday, tours begin at noon. All participants must be 21 or older to tour. Tours are capped at 14 participants. A Boston Brew Mystery Crawl is also offered, as are private tours.

You may also be interested in:

• The Best Hotels in Boston

The Best Whale Watching in Cape Cod

• The Best Weekend Getaways in New England
• The Best Historical Cities to Visit in the USA

Tags: Tours , Boston , Travel , Vacations , food and drink , New England Vacations , US Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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22 best winter day trips from Boston

From cozy getaways to glittery jaunts to the best foodie stops, we found the most fun destinations to hit outside The Hub this winter

Bostonians take winter fun seriously, it’s an integral part of living in the Northeast. Truly, the only way to survive the winter cold is to plan fun activities that get you out of the house. One of the best ways to avoid cabin fever this time of year is to get out of the city. And, a little day trip can really lift the spirits. Explore all that New England has to offer, including quaint, historic towns and shoreline stops, as well as gaming destinations and, of course, buzzing ski towns. And if you don’t have time to head of Boston right now, stick stay closer to home and enjoy the city’s best attractions , best free things to do and best museums in Boston . RECOMMENDED:  The coziest Airbnb cabins near Boston

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Best winter day trips from Boston

1.  Bretton Woods, NH

Located in the White Mountains National Forest, New Hampshire’s stunning Bretton Woods is a winter wonderland spread across more than 2,000 acres, at the base of the tallest peak in the Northeast, Mount Washington. You can take a canopy tour zipline, dine at the mountain top and, of course, glide down the slopes.

2.  Woodstock, VT

Most New Englanders know this bucolic village from summer and fall visits, but they’re missing the beauty of the green covered in a deep snow. It’s the perfect setting for the annual Woodstock Snow Sculpture Festival, held every February. You can also browse Woodstock’s unique shops like FH Gillingham & Sons general store, or the Arts on the Green gallery. Enjoy farm to table dining at the Prince and the Pauper , or grab a pizza and a nice glass of wine at the Ransom Tavern .

3.  Portsmouth, NH

One of our favorite destinations in New England, Portsmouth has a thriving food scene, offers one-of-a-kind shopping, historic walking trails and a beautiful waterfront. Pick a dry day to walk around the shops, then hit Vida Cantina , owned by James Beard nominee David Vargas; or Toscana Italian Chophouse & Wine Bar for a warming bite. Earth Eagle Brewing ’s taproom is a more casual option, with gourmet burgers and dogs that are worth the trip.

4.  Mystic, CT

Scenic, historic Mystic is renowned for stellar attractions such as the Mystic Aquarium and Mystic Seaport Museum . Once you make the 90-minute journey from Boston, you can make a day of it—but if you choose to stay over, try The Whaler’s Inn . Nestled just steps from the banks of the Mystic River and the Bascule Drawbridge, the Inn offers inspired dining at The Shipwright's Daughter . Of course, no visit to Mystic is complete without a meal at The Oyster Club , and a trip to try the award winning pizza at Nana’s Bakery is a must.

5.  Salem, MA

• Things to do

October may be the busiest time of year to visit Salem, but the city is just as fun in the winter. With the Peabody Essex Museum, lots of great restaurants and so many other cultural things to do, Salem is a great day trip from Boston--especially because it is accessible via the commuter rail. So you don't even need a car!

6.  Newport, RI

While you may think summer is the time to visit Newport’s glorious Gilded Age mansions, the annual Newport Winter Festival is among New England’s largest winter celebrations and takes place each February with ten days of events. Along with concerts and a children’s fair, there’s a killer Chili Cook-Off featuring chefs from local restaurants. Treat yourself to a fun, stay at Castle Hill Inn , or stop by The Reef for classic seafood with impressive ocean views.

7.  Kennebunkport, ME

The Maine coastline is always beautiful, but it’s even more stunning to see those mighty waves crash on a snowy afternoon. There’s lots to do too, like Kennebunkport’s annual Paint the Town Red event that stretches Valentine’s Day into a month-long celebration. Dock Square—the town’s unofficial center—is decked out in red twinkly lights, capped with an eight-foot glowing red heart created from lobster traps. Throughout the month, there are special pop-up dinners, mixology classes and wine tastings, many of them offering specials and deals.

8.  Westford, MA

Ski, board, tube and soak in the wintery scene at the Nashoba Valley Ski Area , just 25 miles west of Boston in quiet Westford. This family-owned resort has 18 beautifully groomed trails on 55 acres of terrain. The adjacent, separate tubing park has 18 lanes, making it New England’s largest such facility. Winter events include the annual Grease the Rail Jam and legendary freestyler Wayne Wong’s annual ski clinics with resort co-owner, Olympian Pam Fletcher. It all comes to a splashy end in March with the Meltdown Pond Skim: ski into slush!

9.  Newburyport

Enjoy an off-season stroll through history in this seaport town, on a cool winter day. Start by visiting the Newburyport Historic District, which encompasses most of downtown, and is listed in the National Register of Historic Places and includes the Cushing House Museum & Garden and the Custom House Maritime Museum . After taking in the local lore, dine on classic seafood at Michael’s Harborside or head to the Newburyport Brewing Company , both open year round.

10.  Dennis Port, MA

Is Cape Cod worth the visit in the winter? If you like uncrowded beaches, hiking and getting creative with activities—plus, not sitting in summer traffic—then the answer is yes. Take the under two-hour drive to Dennis Port and head outside to cross-country ski, snowshoe or, if the ground is bare, just walk the Cape Cod Rail Trail for a breathtaking view of the seascape during the winter. Stop by the Pelham House Resort for brunch with an ocean view (without the crowds!) and reserve a private beach bonfire for the whole group with s’more kits and spiked, salted hot caramel cocoa to end your perfect day.

11.  The Inn at Hastings Park

On a Sunday morning finish the weekend with brunch just outside Boston. The Inn at Hastings Park is a historic hotel located a few miles outside Boston.  Offering brunch  on Sundays, this is just the place to escape the city and enjoy the Relais & Chateaux  atmosphere. 

12.  Old Saybrook, CT

Old Saybrook, a very un-touristy town on the coast, is eminently walkable and is  home to the Katharine Hepburn Cultural Arts Center, or The Kate, which is named for the area’s most famous native. You can also explore Saybrook Point and Fort Saybrook Monument Park, and take in the quiet winter beauty of these protected coastal wetlands. Dine at the newly reopened The Essex , a local favorite that’s a Wine Spectator and Yankee Magazine award winner, or pop by the historic Monkey Farm for a more casual experience.

13.  North Adams, MA

North Adams is an old mill town by the Hoosic River that now attracts serious art- and nature-lovers from across the country, primarily due to the spectacular Massachusetts Museum of Contemporary Art, better known as MASS MoCA . Hikers and folks looking for some fresh air head to Mount Greylock, Massachusetts’ highest peak, but bring your snowshoes or a sturdy vehicle in the winter. For Berkshire farms inspired eats, try the Break Room at Greylock Works for a menu that changes daily.

14.  Jackson, NH

If covered bridges iced with snow are your thing, you’ll get a treat heading into this  quiet valley town. Once there, head to the Jackson Ski Touring Foundation’s nonprofit cross country ski and snowshoe center. Considered some of the finest cross-country ski trails in the Eastern U.S., at the main lodge facility you’ll find a retail shop, rental shop and waxing area. There is a trail-warming hut, and ski lessons are available, along with snowshoe tours. After a strenuous day outdoors, dig into a charcuterie board and pan roasted farm sirloin at the Thompson House Eatery .

15.  Watch Hill, RI

Watch Hill in Rhode Island is another popular summer destination that is just as charming in the off season. And perhaps even more so due to the lack of crowds.  Swing by  Ocean House  and the Weekapaug Inn. Be sure to plan your visit so you can spend the afternoon at the  Weekapaug Inn  for lunch and then the evening for dinner at Ocean House.

16.  Westerly, RI

While visiting nearby Watch Hill, or as a stand-alone trip, sweet little Westerly is a decidedly non-touristy town with lots for visitors to do. Take a chilly stroll (or maybe not that chilly, based on the past few winters) on a stretch of Misquamicut State Beach, then head to downtown Westerly for fresh baked doughnuts at Knead , cocktails and oysters at High Hope Tavern and a modern Peruvian meal at Bar Pisco .

17.  Provincetown

With the ferry running into December, and Cape Air year round , there’s no better season than the holidays to visit sassy P-town. Take in the lobster pot “tree,” climb the 252-foot granite Pilgrim Monument for dramatic harbor views, dine year round on great seafood at Mac’s Fish House and enjoy strolling the peaceful streets.

18.  Brattleboro, VT

Brattleboro —a funky, artsy destination in the foothills of southern Vermont’s Green Mountains—is surrounded by wonderful hiking terrain, but you might also want to explore the town’s bohemian shops and farm-to-table eateries. Go vegan at the Superfresh! Organic Cafe, or head to the Chelsea Royal Diner, an original 1939 Worcester Lunch Car. In February, the annual Winter Carnival brings together the arts and entertainment communities for a weeklong jamboree. Visit the Vermont Jazz Center or one of the many artisan breweries. To learn about local history, stop into the Brattleboro Historical Society, which has a wonderful collection of memorabilia.

19.  Providence, RI

This easy to navigate city should be on your radar year round for a day trip. Put on your warmest winter coat and treat yourself to a dine-around through Federal Hill, the city’s impressive Italian neighborhood, loaded with Italian eateries and shops. Visit the Rhode Island School of Design’s museum , which includes one the country’s finest university art collections, and don’t miss celebrated Syrian bakery Aleppo Sweets .

20.  Groton, MA

Head to this classic New England town and enjoy a brisk stroll around the Rocky Hill Wildlife Sanctuary , home to uninterrupted woodlands and ample solitude, and enjoy more than three miles of hiking trails while keeping an eye out for moose, beavers and porcupines, as well as nearly 100 species of birds. Other options include hiking Gibbet Hill Farm and exploring historic Bancroft Castle . If you’re visiting on a weekend, check to see if Puritan & Co.’s Will Gilson is cooking up dinner at his family farm, the Herb Lyceum .

21.  Uncasville, CT

If you’re not feeling outdoorsy, plug into the nightlife at Mohegan Sun . The casino is essentially a giant indoor winter playground packed with restaurants, bars and entertainment venues. The gaming tables and slots are one option, but you can also catch a comedy or music act. In January, the annual Sun Wine and Food Fest adds three days of wine, beer, and spirits tasting, plus celebrity chef demonstrations.

22.  Everett, MA

There’s one major reason to head to Everett, and that’s the relatively new Encore Boston Harbor Casino. Stay warm and cozy 24 hours a day while you hit the tables, or enjoy a relaxing massage in the resort's luxurious spa (which is offering winter skin saving treatments, like the Skin Replenishing Ritual, all season long). Sample new flavors at Cheese Meet Wine or bet on the Pats at Wynn BET Sports Bar .

More foodie fun

The best food-filled road trip from Boston

It doesn't get much better than food and travel—why not combine the two and take a food-focused road trip? Here's a go-to itinerary for anyone looking to take in the area's best treats and culinary experiences. Given New England's relatively small footprint, you can mix and match these stops based on your liking.

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10 Things to Do in Boston in the Winter

Is Boston worth visiting in the winter? While chilly Boston might not inspire the same kind of excitement as warmer destinations, don’t be quick to dismiss Boston from your list of winter vacation contenders. With its illuminated trees set against a backdrop of historic brownstones and cobble-lined sidewalks dusted with snow, Boston from November to February undergoes a winter wonderland transformation that most US cities only dream of recreating . 

Seeing snow for the very first time is enough of a draw alone for some bucket-list travelers. But if you find the frigid temperatures challenging, not to worry: we’ve included a packing list at the end of this article with everything you need to keep yourself warm and comfortable while you’re out exploring. And when you’re ready for a rest, you’re sure to find a cozy spot right in front of the fireplace at HI Boston hostel . 

Still wondering if Boston is worth visiting in the winter? Here are 10 great things to do that will make you love Boston in the winter!

1. Go ice skating on Boston Common’s Frog Pond

Lace up those skates and join the merrymaking with locals and visitors of all ages at Frog Pond. Whether you’re a first-time skater or a seasoned veteran on the ice, gliding around one of the best outdoor rinks in the USA, in the country’s oldest public park, never loses its charm. The rink is open daily from December to March with ice skates and lockers available for rent. Order some hot cocoa to warm you up between laps.

2. Chill out in an illuminated igloo at The Lookout Bar

Thanks to the growing popularity of “pop-up” experiences around the country, Boston’s winter nightlife offerings have never been hotter. Starting in early November, the Lookout Rooftop Lounge on top of The Envoy Hotel in Boston’s Seaport District is outfitted with its famous “Ice Boxes.” These LED-lit plexiglass igloos can hold up to six people and come with their own thermostats and complimentary blankets. Sip on their winter-inspired seasonal cocktails while soaking in a sweeping view of a glittering skyline and Boston Harbor.

3. Tour around the Taza Chocolate Factory

Chocolate enthusiasts will delight in a multisensory tour of Boston’s very own chocolate factory. Taza Chocolate is a social enterprise producing stone-ground Mexican chocolate, a grittier dark chocolate quite unlike the processed sweets found in most grocery stores. This hour-long tour gives you an inside look at the company’s chocolate-making wizardry, highlighting everything from their ethically sourced cacao beans to their iconic disk-shaped bars. And did we mention they don’t skimp on their free samples? Get ready for some toothsome fun that won’t break the bank.

4. Hitch a ride on Boston’s Old Trolley Tour 

Keep the cold at bay while taking in the city’s historic gems on the hop-on, hop-off Old Trolley Tour. The vintage trolley car operates year ‘round, rain or shine, and is fully heated. The full tour showcases 18 of Boston’s top attractions with engaging commentary from the trolley conductors, which is especially helpful if you’re visiting Boston for the first time and want to cover the most ground without having to walk or take the subway. And if you want to get off and take time savoring a particular stop, each ticket allows unlimited re-boarding.

5. Sample a taste of Boston’s best brews

The Boston brewery circuit is synonymous with good times. $5 at Harpoon Brewery and Beer Hall in the Seaport District nabs you unlimited samples of Mass. Bay Brewing Company’s range of libations. At the beer hall, don’t forget to order their pillowy, fresh pretzels, made with the brewery’s leftover beer grains. For those who like things a little more mainstream, visit the Sam Adams Brewery in Jamaica Plain. Named after one of America’s Founding Fathers, it offers visitors a free tour of its factory operations. Just make sure to reserve ahead of time as the free tour is in high demand.

6. Become a whisky connoisseur at Boston Harbor Distillery

Beyond the standard brewery tour awaits a more refined sampling experience at the Boston Harbor Distillery in Dorchester. Situated in a historic warehouse on the waterfront, women-owned Boston Harbor Distillery stocks barrels of whiskey varieties and has even created a whiskey made from aged Sam Adams beer.

7. Root for your favorite team at a TD Garden game

In this world-class sports city, nothing is more Bostonian than catching a Boston sports game. The winter sports calendar is the prime time to score reasonably priced tickets to see the Boston Bruins hockey team and/or the Boston Celtics basketball team in action. The two teams play at TD Garden on an almost daily basis in the winter and every game is fully indoors. Plus, nothing gets the heart pumping as much as being surrounded by a crowd of Boston sports fans, who are in a league of their own thanks to their brazen attitudes and colorful language. 

8. Sip on innovative cups of hot chocolate

Nothing will thaw you faster than a piping hot cup of hot chocolate. Lucky for you, Boston has no shortage of great cafes featuring not-so-average mugs of hot cocoa. Try the famous Drinking Chocolate at L.A. Burdick’s Chocolate Café ordered either dark, milk, white, or spicy. Gâté Comme des Filles counter-only service in Bow Market carefully concocts Parisian-style hot chocolate served with a thick dollop of whipped cream. Get your dark hot cocoa fix at Curio Coffee, utilizing local Taza chocolate that pairs like a dream with their liege-style waffles. And if you like hot cocoa on the bolder side, visit Flour Bakery for their fiery hot chocolate spiked with chile and cayenne pepper for that extra heat.

9. Support small businesses at an indoor market

Of the many things to do in Boston during the winter, nothing provides more respite from the cold than visiting its indoor marketplaces. The most popular with tourists is Faneuil Hall and Quincy Market , but a stone’s throw away is the lesser known Boston Public Market . Located right next to the Haymarket subway stop, this food hall is home to 30 New England culinary small businesses, each offering artisanal goods and a gourmet spread of the region’s best ingredients. In Union Square, the recently opened Bow Market is a haven for independent creative retailers with a vibrant community feel. You can get everything from adorable stationery to Korean bibimbap bowls. If you’re more into eccentric purchases, the five-story Cambridge Antique Market never fails to impress with its vast array of vintage finds.

10. Experience holiday fun Boston-style

Around the holidays, there are some delightful seasonal experiences that add to Boston’s magical winter quality. Year after year, the Boston Ballet enchants with its annual performance of the holiday classic, The Nutcracker .

If you’re a fan of DIY holiday light installations, enjoy the Illuminations Tour around Somerville to support local businesses while admiring the electric frivolity of facades decked with lights, ornaments, and tinsel. Situated northwest of Boston’s Downtown, Somerville is another city part of the Greater Boston area and can easily be reached by subway (or “T”) on the red line. The Illuminations Tour has been traditionally run as a trolley tour but was converted into a walking tour in 2020 in response to the pandemic. A digital map is available online for you to follow.

Now in its sixth year, the 2021 SoWa Winter Festival brings the revelry of Europe’s Christmas market traditions to Boston. From December 3 to 13, scour the 100 vendors on display for the perfect souvenir, holiday gift, or tasty treat.

What To Pack for Your Visit to Boston in the Winter

When in doubt, layer up. Invest in heattech undershirts to hide beneath chunky knit sweaters. Bring a puffer jacket that’s water- and windproof to keep you extra toasty. 

Winter accessories are essential to fighting wind chill: don’t forget gloves, a scarf, and a warm beanie or earmuffs to keep those ears warm. Last but not least, sturdy, waterproof shoes or boots with good grips are the best when combating sidewalks covered in snow, puddles of slush, or even black ice. And make sure your feet are extra insulated with warm socks. If I know I’m going to be walking around for a long time, I’ll wear long john trousers underneath my jeans too. One can never be too prepared for extreme weather in Boston, especially during winter.

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Things to Do in the Winter

Winter Things to Do in Boston

When the temperature starts to drop and the winter season begins, there’s still plenty of fun to be had in Boston. Whether visiting many of the city’s most popular indoor attractions or enjoying events and other seasonal activities, here are some of the top things to do during winter in Boston.

Discover the magic of wintertime in Boston and embark on a historical “Transportainment ® ” adventure!

Go Ice Skating at Frog Pond

One of the most popular spots in the city to go ice-skating, Frog Pond is located within Boston Common . You can rent skates or bring your own and the café offers delicious hot cocoa to warm you up when you need a break.

Take the Old Town Trolley Tour

A great way to see all the sights, the Old Town Trolley Tour will take you to more than 100 of the city’s most popular attractions and historical sights . Along the way, you’ll be entertained by the onboard conductor and have no need to worry about finding parking around the city. Hop on and off as often as you wish and check out all that Boston has to offer.

Holiday Tree Lighting Ceremonies

If you’re visiting Boston in December , you can get into the spirit of the season by enjoying several different tree lighting ceremonies. The Boston Common ceremony takes place in early December and includes games, prizes and activities such as the lighting of the special tree that was a gift from Nova Scotia. There are also ceremonies at Copley Square and the Commonwealth Avenue Mall. Experience the sparkling lights and merriment that signifies the beginning of the holiday season in Boston.

First Night

One of the most popular events in Boston is the special New Year’s Eve celebration that takes place in several Boston neighborhoods. First Night attracts more than a million people each year and includes fireworks, live performances, a grand parade, crafts, ice sculptures and more.

Hanukkah Celebration at Faneuil Marketplace

Bring the family and enjoy music, crafts, delicious latkes, jelly doughnuts, Hanukkah gelt and games for the children. The Freedom Menorah will be lit and dedicated to the victims of the Boston Marathon bombing. Check online for the date and time of this family event.

Relive the Boston Tea Party at the Annual Reenactment

Returning in 2023 

Annually on December 16 , visitors and locals gather to commemorate the fateful night that forever changed America’s history. The event begins at the Old South Meeting House as you join more than 100 re-enactors who bring the Boston Tea Party to life. You’ll march alongside the colonists to Griffin’s Wharf, dump tea overboard and learn about the Boston Tea Party and how it sparked the American Revolution.

Old Town Trolley’s Holiday Sights & Festive Nights Tour

Take in the fun and merriment of the holiday season on an Old Town Trolley Holiday Sights & Festive Nights Tour ! You’ll have a front-row seat as you experience the dazzling lights and splendor of the season, riding through town as carolers fill the night air with music. Add complimentary seasonal beverages and snacks, and you’re all set for what promises to be a new holiday tradition in Beantown!

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BOSTON TOURS

Boston's best tours now offering small group public walking tours.

Simply The Best Boston Sightseeing Tours

Experience Boston - a historic & vibrant city, on a private tour with your own personal guide. With its rich history, diverse neighborhoods, and legacy of arts, culture., dining, education, and sports, there is something for everyone! We are passionate about our city, and we look forward to sharing it with you.

This is not a mass-market tour. We offer customized private tours in Boston that deliver more of what you want to see. While most Boston tours will touch on the highlights of this great city, we want to show you all that and more. We believe that visiting Boston should be fun. We'll give you the stories behind the scenes through the eyes of the locals. Walking along the iconic Freedom Trail, you'll hear stories from the American Revolution. Plus, you'll hear unique stories, like how a deadly wave of molasses once flooded Boston's North End and why the locals never say "Beantown".

Come and experience Boston at your own pace. How to explore the city is entirely up to you. We offer walking tours, driving tours, and step-on bus guide services. It's our goal to make sure you see as much as possible while having fun along the way. You just might learn a few things too!

BOSTON SIGHTSEEING TOURS

Freedom Trail Walking Tour

TOURS START MAY 14th! Tours will run on Tuesdays and Thursdays. Additional days coming soon!

Experience more than 250 years of history on Boston’s Freedom Trail a red brick line connecting historically significant sites.

Most Freedom Trail tours only cover half of the trail. Our 3 hour tour will show you everything from the Boston Common to Copp's Hill - 14 sites in all plus many other interesting things to see and stories to hear!

The Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.

Tour-in-Four -- 4 Hour Private Tour

A four-hour combination walking and riding tour. In this extended tour, you will stroll through the historic North End. Perhaps have a snack from a famous North End pastry shop. See the Old North Church and Paul Revere's house, Explore Copp's Hill Burial Ground and learn about the "Spite House", the "Brink's Job" robbery. and the Great Molasses Flood and so much more. Stroll through the cobbled streets near Faneuil Hall and learn about our Revolutionary War past. Drive through downtown, Historic Beacon Hill, the Back Bay, and Fenway. If time permits head over the Charles River to MIT & Harvard. Travel through the new and vibrant Seaport District and along the beautiful Boston Harbor.

Private Freedom Trail Tours - 3 Option Available

Experience more than 250 years of history on Boston’s Freedom Trail which is a 2.5 mile red line connecting 16 historically significant sites.

The price listed for for all walking tours is for up to 10 participants. Each additional guest is $10.00/person up to 30 people.

The Overview Tour -- 2.5 Hour Private Tour

This tour covers the many exciting sites & attractions of Boston, Cambridge & Charlestown in a short amount of time. See sites along the waterfront, through the North End, Charlestown, The West End, Beacon Hill, Back Bay, and Cambridge, if time permits also see portions of Harvard and MIT.

The Everything Tour -- 5.5 Hour Private Tour

The name says it all. This exciting journey covers all major sites with a stop for lunch. In this detailed excursion you will experience all of the sites & attractions we offer.

Beacon Hill Private Walking Tour

Beacon Hill is one of the oldest and most picturesque neighborhoods in America. From the golden dome of the State House to the luxury homes of Louisburg Square, this tour takes you by picturesque streets, highlighting examples of early American Federal, Greek Revival, and Victorian architecture.

Learn about Boston's first settler, Reverend William Blackstone, a reclusive clergyman. Hear about Robert Gould Shaw and his role in leading freed slaves in the Civil War. Walk portions of the Black History Trail and stroll along the famous cobbles of Acorn Street.

Cheers! Beacon Hill & Back Bay Combo Private Tour

Starting atop Beacon Hill by the gold domed 1798 State House, stroll through these historic neighborhoods, one from the early and the other, late 1800’s.

The elegant red brick sidewalks and Federal style townhouses of Beacon Hill have attracted residents from Louisa May Alcott to John Kerry. See the cobblestoned street that is the most photographed in the city, and hear of the famous residents in this charming exclusive Historic District. Architectural detail, flowered window boxes, and wrought iron finishes decorate these magnificent homes.

Back Bay & Copley Square Private Tour

In this exciting and historic excursion you will learn how it earned its name and how its progressive development during the 1800’s birthed some of America’s most renowned architectural wonders. You will view Boston’s memorable mansions and grand townhouses along Commonwealth Avenue.

The Underground Railroad/Black Heritage Trail Private Tour

The Underground Railroad was not a railroad or underground but it did have real live conductors who gave their lives so Slaves could be free. Underground railroad is a symbolic name used for over 200 years to break away from slavery.

Historic Salem Private Walking Tour

See where history and mystery converge in a captivating walking tour of Salem! This 3-hour journey offers a comprehensive and immersive experience of Salem, providing a blend of maritime history, colonial heritage, and the captivating stories that have shaped this iconic city. No admissions are included. Optional admission to any attractions – add one hour

Join us for a private exploration through time and tales in the heart of Salem!

Lexington & Concord Private Tour (in your car with our guide)

Travel 16 miles outside the city to the nearby communities where America was born. You’ll hear stories of brave individuals on both sides of the Revolutionary War and have an accurate, vivid picture of the action of April 19, 1775. History will come alive as your guide retells the story of the morning skirmish on quaint Lexington Green where 77 Minutemen stood against 700 British Red Coat soldiers in the first encounter of the Revolutionary War. A charming town, its Green has been carefully preserved and features several statues and historic monuments. View many colonial homes from the 1700’s around the Green and along our route.

*This tour requires our guide to ride along in your vehicle.

Plymouth Private Walking Tour

Walk where the Pilgrims trod and hear how their faith inspired them to flee from England, find refuge in Holland, and cross the ocean to the shores of New England.

This tour will help you understand the monuments of Plymouth erected in honor of her founders as you hear the stories of these Separatists in their own words.

Other Local Areas to Visit

We now offer custom group bus charter tours to areas outside of the city core including Plymouth, Salem, Marblehead, Gloucester & Rockport, Lexington & Concord. Give us a call to discuss your plans!

Why choose us?

See More With Our Knowledgeable Local Guides!

Our guides are well-versed in Boston's fascinating history, architecture, culture, and food. They'll show you local favorites like Fenway Park, the Boston Marathon finish line, and the bar from Cheers. You'll get the local perspective on Boston's arts, culture, food, education, and sports legacies. There is something here for everyone, and our guides can't wait to share it all with you!

Custom Tours

Custom Tours are our specialty. Let us design one for you!

We specialize in setting up just the right tour for you. We can arrange visits to museums, add stops along the way, coordinate to areas further out of town and anything else that you wish to see.

Step-On Services

Step-On Services for schools & larger groups.

Got a bus? No problem! Need a bus? Again, no problem! We work with area charter bus companies to bring you many different options for small or large groups that are needing transportation services

Top Rated on Trip Advisor & other travel review sites!

Tour with confidence knowing that we are highly rated on many travel review sites. We are often recommended by concierges from Boston area hotels and travel professionals as well as visitors from around the world.

Explorations In A City Of Firsts

As one of America's oldest cities, Boston can proudly claim many "firsts." The first public park, Boston Common, is across from the Massachusetts State House in the Beacon Hill neighborhood. The Boston Public Library, founded in 1852, is the first extensive free municipal library. The first subway system in America opened in downtown Boston in 1897. And the first lighthouse in America was established in Boston Harbor on Little Brewster Island in 1716. We boast the first telephone call, the first public school, the first computer, and many, many more!

Boston, and the surrounding area, are also home to many great inventions. The disposable razor was patented in 1901 by King C. Gillette. The 54th Massachusetts was the first unit in the Union Army made up of free Black soldiers in the Civil War. And the original Toll House Chocolate Chip Cookie was invented in nearby Whitman, MA, by Ruth Wakefield.

Frequently asked questions

What are private tours.

Private tours include just you and your family and friends. That’s all. To ensure you have a personal experience, your group will consist of you and your family/friends/colleagues, only. We never mix groups, or put you with strangers. There is no minimum: if it’s just you, we look forward to becoming your travel companion for the day.

Do you offer private tours for larger groups?

Yes! Larger groups include tour group on a bus, school groups, corporate groups, etc. Tours for larger groups range in size from 10 to upwards of 60 or more people. For information and pricing on group tours for other organizations, please contact us.

What if someone in my group has mobility issues?

We will work with you to the best of our ability to ensure you’re able to enjoy our city at a comfortable pace and within a reasonably safe, respectful environment.

Where does the tour begin?

Starting points can vary depending upon the tour that you choose. Private tours can often begin at the Boston location of your choice including hotels, B&B’s private homes, etc. or a designated meeting place will be determined prior to tour day. The Freedom Trail tours begin at the corner of Hanover Street and Cross Street at the Tony DeMarco boxing statue or the corner of Park Street & Tremont Street between the Park St. subway stations.

Are prices per person?

No! Prices are per group, in US dollars. The price of your tour is guaranteed the moment we receive your deposit.

Are there any additional fees or admissions?

Optional admission to the Old North Church - $5.00 and Paul Revere House - Adults - $5.00 Seniors and College Students - $4.50 Children (ages 5-17) - $1.00 Cash only for admission. Old State House Museum optional visit admission: Adults - $10.00 , Seniors (62+) - $8.50, Students - $8.50, Youth (6-18), Members, US Military, and Veterans - FREE

A booking fee is added to bookings made online through the reservation service. Call us with questions or for additional details.

What forms of payment do you take?

We accept all major credit cards, Venmo or company check in advance of your tour.

What is the cancellation policy?

BTS must receive written notification of cancellation. The date such notification is received by BTS will determine the applicable cancellation penalties. The following cancellation penalties apply:

• More than 90 days prior to participant's scheduled tour date, 100% of paid contracted tour amount will be refunded by BST.
• From 21-90 days prior to participant's scheduled tour date, 50% of paid contracted tour amount less any costs associated with ground transportation will be refunded by BST.
• From 14- 21 days to scheduled day of participant's tour date 25% of paid contracted tour amount less any costs associated with ground transportation will be refunded by BST.
• Any cancellation of tours less than 14 days prior to participant's scheduled tour date, no refunds will be issued will be refunded by BST.
• For tours requiring use of a third-party vehicle, no refunds are available if the notice given conflicts with the third-party cancellation policy.

Do you accept gratuities?

Tipping is by no means a requirement or expectation for anyone on our team. If you had a great tour and enjoyed the service that your guide provided then leaving a tip is always greatly appreciated. This can be done with cash, Venmo or added to your invoice.

When are tours offered?

Tours run year round. Select the date on our reservations calendar and a tour representative will respond to confirm the date and time you prefer is available.

What about the weather?

This is New England. We are a hearty bunch and will go out in all kinds of weather. If it rains, we can spend more time inside of attractions and dodge the puddles while using an umbrella. Flexibility is the name of the game! We reserve the right to cancel any tour if the weather conditions are determined to be unsafe.

How do I book a private tour?

To book a private tour for up to 6 people you can book online or call us at 866-817-TOUR. To book a tour for a larger group contact us by email or telephone. Please note that as we are often out giving tours, phone calls are returned in the late afternoons or evenings.

Can I order a gift card?

Yes! We offer virtual gift cards for any amount which can be sent to you or directly to the recipient. Simply click here.

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Winter on the Waterfront

While the days are shorter and colder weather is setting in, there’s still so much to see and do on your waterfront!

Explore miles of Boston’s Harborwalk , warm up at a local business, or tap in to virtual events at home. Take our recommendations for dining, art & light installations, and activities to help you make the most of the waterfront all winter long. Whatever you choose, go ahead and #BundleUpBoston, and enjoy your waterfront!

Events & Activities

Winter Wander on Peddocks Island

Experience an unforgettable winter day as you wander the trails of Peddocks Island in search of winter tracks and traces. Enjoy a guided walk, play in the snow (if the weather cooperates), or join us by the fire for s’mores by our fire pit.

• Saturday, February 24, 2024 | 11:00pm -3:30 pm | REGISTER

Revelry and Revolution: An Evacuation Day Harbor Cruise

Learn the real history of the British evacuation of Boston in 1776 on a harbor excursion featuring live historical narration, live music, and close-up views of Boston Light: America’s first light station.

• Saturday, March 23, 2024 | 11:00pm -3:30 pm | REGISTER

Revolutionary Harbor Lecture Series

Join the National Parks of Boston for this special winter lecture series running monthly, January through March.

What’s the Tea? The Boston Tea Party’s Impact on Boston and its Harbor | Tuesday, February 13, 2024 | REGISTER

Women’s History on the Boston Harbor Islands: The Great Brewster Journal | Wednesday, March 20, 2024 | REGISTER

Merry Moakley at Moakley Park

Join us for a family-friendly evening of festive fun with pizza, music, hot cocoa, crafts, free books, photos, games, and more.

• Thursday, December 7, 2023 | 3:30 – 6:00 pm

11th Annual Waterfront Ice Sculpture Stroll

Our signature Waterfront Ice Sculpture Stroll is back! Get ready to count down to 2024 with more than 30 ice sculptures hosted by businesses and cultural sites across the waterfront – the largest Stroll EVER!

• Sunday, December 31, 2023 | 1:00pm -5:00 pm | MORE INFORMATION

Friends of the Boston Harbor Islands New Year’s Day Boat Trip to Thompson Island

Join the Friends of the Boston Harbor Islands for a New Year’s Day boat trip to Thompson Island!

Enjoy a 45-minute boat ride through the Boston Harbor Islands and a panoramic view of the Boston skyline. Explore Thompson Island’s meadows, forests, beaches, and 40-acre salt marsh and learn about its intriguing history.

• Monday, January 1, 2024 | 12:00pm -4:00 pm

Winter Wildlife Cruise

Grab your camera and binoculars and join park rangers and local naturalists to observe animals who make their wintertime home in Boston Harbor and around the outer Harbor Islands.

• Saturday, January 20, 2024 | 11:00pm -3:30 pm

New England Boat Show

The 2024 Discover Boating New England Boat Show has a wide selection of boats, an abundance of must-see attractions, and fun features for all ages.

• Wednesday-Sunday, January 10 – 14, 2024 | 10:00am – 2:00 pm | LEARN MORE

Winter Warmer at Moakley Park

Come to Moakley Park for a free, fun afternoon complete with warm drinks, yummy snacks, games, crafts, and more: Enjoy s’mores, popcorn, and hot cocoa Catch a musical performance Make Valentines for community elders Play yard games like Spike Ball & Cornhole Pick a book to take home Share your favorite Moakley memories & chat with friends around a fire.

• Saturday, February 10, 2024 | 2:00 pm-4:00 pm | REGISTER

Explore Your Waterfront

Hold on to your handwarmers — the Seaport’s been shaken up in a giant snow globe and transformed into a magical winter getaway. Find gifts, treats, activities, and plenty of surprises in this one-stop wonderland you can enjoy all season.

• Through February 2024 | LEARN MORE

Boston’s Black Heritage Trail

The Black Heritage Trail® is a 1.6 mile walk through the heart of Boston’s Beacon Hill neighborhood. The trail showcases residences and community buildings associated with a Black community that thrived on, and near, the north slope of Beacon Hill before, during, and after the American Civil War.

• Daily | LEARN MORE

Art & Lights

Christopher Columbus Waterfront Park Holiday Trellis Lights

Bundle up and enjoy the the ambiance of the Christopher Columbus Parks iconic trellis ablaze in blue lights to commemorate the Holiday Season!

• Through January 2024 | LEARN MORE

Ship Lights at Martin’s Park

Martin’s Park at the Smith Family Waterfront is a climate-resilient park built in memory of eight-year-old Martin W. Richard, the youngest victim of the 2013 Boston Marathon bombing. The accessible park provides play opportunities for children, families, and visitors of all abilities. The wooden play ship is the centerpiece of the space that will be lit for the holidays.

• Through February 2024 |  LEARN MORE

Hatchling on The Greenway

Created by interdisciplinary design team Studio HHH, Hatchlings is a 100% solar-powered installation that pays joyful homage to one of Boston’s architectural gems and envisions a brighter, more environmentally sustainable future for our city. This creative activation will provide Bostonians with an experiential destination during the coldest months of the year while showcasing an innovative and sustainable approach to holiday lights.

ICA Free Thursday Nights

The ICA is free for all visitors every Thursday evening. Tickets for Free Thursday Nights will be available at 10 AM on that Thursday morning.

• Every Thursday | RESERVE TICKETS

Fitness and Wellness

Winter Harbor Hikes or Runs

Start your year off on the right foot with a self-guided walk along Boston’s Waterfront. Check out one of four recommended routes around the harbor to get outside and get moving!

• Castle Island – Dorchester Heights – 2 miles
• Paul Revere House to Bunker Hill Monument – 1.3 miles
• Boston Harbor Islands Welcome Center to Seaport – 1.3 miles
• Maverick Station to Hyatt Regency Boston Harbor – 1.5 miles

Support our programs!

Boston Harbor Now is a 501(c)(3) nonprofit organization. Our programs would not be possible without the support of our generous donors. We hope you will consider joining your neighbors with a gift in support of our community programming.

THE 10 BEST Boston Tours & Excursions

Boston tours.

• Historical & Heritage Tours
• Walking Tours
• Sightseeing Tours
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Likely to Sell Out
• Special Offers
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Boston Hop-On Hop-Off Trolley Tour with 14 Stops

2. Freedom Trail: Small Group Tour of Revolutionary Boston

3. Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

4. Tour of Historic Fenway Park, America's Most Beloved Ballpark

5. Boston Whale Watching Cruise by High-Speed Catamaran

6. The Revolutionary Story Epic Small Group Walking Tour of Boston

7. Boston Duck Boat Sightseeing City Tour with Cruise Along Charles River

8. Boston Small-Group Walking Food Tour With Tastings

9. Boston Harbor Sunset Cruise

10. Brunch in a Crunch in Boston

11. Boston Tea Party Ships & Museum Admission

12. Boston Ghosts and Gravestones Trolley Tour

13. Boston Historic Sightseeing Harbor Cruise with Up-Close View of USS Constitution

14. Boston Freedom Trail Daily Walking Tour

15. Harvard University Campus Guided Walking Tour

16. View Boston Observation Deck Admission Tickets

17. Boston Seafood Lovers Adventure

18. Boston to Plymouth Day-Trip including Quincy, Plimoth Patuxet and Mayflower II

19. Boston Signature Dinner Cruise

20. Martha's Vineyard Day Trip with Optional Island Tour from Boston

21. 1 or 2 Day Hop-On Hop-Off Trolley Tour with Harbor Cruise Option

22. Boston Harbor Sightseeing Cruise

23. French Steakhouse Dinner Cooking Class in Boston

24. Boston: North End to Freedom Trail - Food & History Walking Tour

25. Salem High Speed Ferry to/from Boston

26. The Small Group Boston Tour, I know secrets that others don't!

27. Sightseeing Day Sail around Boston Harbor

28. Walking Tour Downtown Freedom Trail + Beacon Hill & Copley Square

29. Boston Small-Group Freedom Trail History Tour Pub Crawl

30. Boston to Newport Small-Group Day Trip with Breakers & Marble House Admission

What travelers are saying.

• GrandTour41823227275 1 contribution 0 5.0 of 5 bubbles Bunker We were on three different trolleys. Bunker was amazing!!! He was the best. His commentary was excellent!!! His driving was excellent. Very enjoyable!!! Read more Review of: Boston Hop-On Hop-Off Trolley Tour with 14 Stops Written April 28, 2024 This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

• Freedom Trail: Small Group Tour of Revolutionary Boston
• Tour of Historic Fenway Park, America's Most Beloved Ballpark
• Boston Hop-On Hop-Off Trolley Tour with 14 Stops
• Boston Tea Party Ships & Museum Admission
• Harvard University Campus Guided Walking Tour
• North End Boston Food Tour
• Intrepid Urban Adventures - Boston
• Mobsters and Lobsters
• Walk & Talk Boston Walking Tours
• Trailblazer Tours Boston - Private Tours
• Cambridge Historical Tours
• Night Rider Private Charters of Boston
• Boston Chinatown Tours
• PhotoWalks Tours
• Boston Foodie Tours
• Tuckamore Aviation
• The Motorsport Lab
• New England Aquarium Whale Watch
• Boston Crime Tour
• Boston Segway Tours
• Boston's "Politically Incorrect" North End Food Tour

Walking Tours

Our walking tours.

Boston By Foot tours offer opportunities for visitors and locals to explore Boston’s cityscape and discover its history with a passionate and knowledgeable guide. Core tours are offered on a daily and weekly basis during the April-November tour season, while others are offered monthly or quarterly. All tours are available upon request as a private tour at any time.

View tours by frequency, topic or by schedule by accessing our calendar . Each tour page contains detailed information about each of our offerings. We look forward to sharing our love of Boston with you!

PLEASE NOTE: Registration for all public walking tours closes one hour before tour start time.

Explore by Category

Daily & weekly, beacon hill, boston by little feet, the dark side of boston, heart of the freedom trail, the north end: boston's immigration gateway, reinventing boston, road to revolution, monthly & quarterly, art, architecture and gardens, back bay’s victorian architecture, bay village, becoming back bay, before boston: shawmut peninsula through 1630, ben franklin: son of boston, black voices: writers for a 19th century revolution, boston reborn: after the great fire of 1872, boston’s chinatown, boston's gilded age, boston’s lgbtq past, boston’s loyalists, bulfinch triangle, change and response: boston’s architecture, commonwealth avenue, east cambridge, fort point and seaport: the evolution of the south boston waterfront, the hub of literary america, jewish beacon hill, johnny tremain’s boston, leather district, louisa may alcott’s boston, north end by little feet, remarkable women of jamaica plain, rethinking boston brutalism, the rose f. kennedy greenway, rowes wharf: sensationally good city making, annual events, footloose on the freedom trail, beacon hill with a boo, new for 2024, art introspective: copley square to the south end, boston common: past lives and hidden stories, boston's city hall, sam adams' boston, slavery and abolition in massachusetts, sails & cruises.

Offered in partnership with the Charles River Boat Company and the Liberty Fleet of Tall Ships

A Sail Through Time

Architecture cruise, private tours, book a boston by foot private tour.

Boston By Foot private tours are perfect for family groups, school groups, corporate groups, university and alumni groups, people who wish to tour with their pets, and anyone looking for a more personalized tour experience.

Any of the walking tours listed on our website can be booked upon request as a private tour. Please review the available tours using the category tabs on the right.

Our ability to offer you your preferred tour at your preferred time will depend on the availability of our guides. Some tours have more limited availability than others. Unfortunately we are not able to offer tours on the same day of a request, nor are we able to guarantee tours without enough notice. We kindly request at least 1-2 weeks notice to make arrangements.

If you are unsure of what tour would be most suitable for your group, please note this in the booking request form and we’ll be happy to assist. There is no minimum attendance requirement, but tours of 12 people or fewer are charged at a flat rate. Larger groups are charged on a per-person basis. Multiple guides will be scheduled for larger groups.

Book a Private Tour Online Request a Tour for More Than 20 People Request a Specialty Tour

Limited tour options available in Spanish, French, German, Italian and Mandarin. ASL interpretation available with notice. Please note that we do not offer step-on services, driving tours, or tour guide services lasting more than three hours.

Additional Tours by Request

Adams family in boston, adventures at sea, art deco in the back bay, art deco in boston’s financial district, avenue of the arts, beacon hill from both sides, boisterous bostonians: riots & protests, boston by bulfinch, boston common and the public garden, the custom house historic district, dams, bridges & locks, east boston: maverick square and beyond, davis square, fierce and feminine: great women of boston, finding aesop’s fables in copley square, the esplanade, the flat of beacon hill, fort point channel, historic waterfront, grave undertakings, in washington's footsteps, jewish north end, the ladder blocks, literary beacon hill: the 20th century, notable women of beacon hill, longwood & cottage farm, the making of mit, the north slope of beacon hill, old west end, road to the vote: boston suffragists, south boston’s broadway, taverns to tea houses, upham’s corner, architectural darwinism, working women: boston women find their voice, boston’s french connection, boston’s opera history, decline and rebirth of a city, harvard yard, mission hill, murder, martyrs, and mysticism, roxbury highlands, sowa: south of washington street, our virtual programs & tours.

Though we love exploring Boston in person, we recognize that it's not always possible. For these situations, we offer a range of virtual tours and presentations that can be viewed from anywhere. A series of these programs are offered on our public program calendar each winter and can also be booked upon request at any time. These virtual programs are perfect for school groups, corporate team building, libraries, community centers, or just a group of friends who would like to experience our tours without traveling into Boston.

The following presentations can be booked at any time, anywhere, pending guide availability. Please contact our office at [email protected] for details.

2024 Winter Programming

Trinity church: revolutionary church in copley square (2-part series), preservation of the charles street meeting house, the downtown waterfront: boston's forgotten redevelopment project, the trailblazing life of susan dimock, m.d., boston's innovation trail, boston's music history: a tasting menu (3-part series), boston's great fire of 1872, programs by request, boston in the 21st century, murder, mayhem and martyrs.