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

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!

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 Trail 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. 

12. 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!

16. 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!

• Daedalus

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.

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

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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

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