Don’t Let Winter Freeze Your Fun: 21 Things to Do in Boston in the Winter

Exciting Things to Do in Boston in the Winter

Yes folks, it’s officially winter. We know you want to hunker down at home and hibernate for the season (trust us, we do too), but if you find yourself a tourist braving Boston’s chill or a local getting a little stir-crazy, we’ve got you covered. There are plenty of things to do in Boston in the winter, and this city knows how to make the cold months feel downright magical. From cozy indoor escapes to festive outdoor adventures, consider this your go-to guide for staying entertained all season long—so you better get cracking on this list!

Cozy Private Food Tour

Just because our public food tour season is on pause until spring doesn’t mean the fun has to stop. In fact, if you’re looking for things to do in Boston in the winter, exploring the city through its food scene is one of the coziest (and tastiest!) options around. Winter is the perfect time to savor comforting bites, discover local gems, and warm up with friends while experiencing Boston in a whole new way. Bites of Boston is here to make it extra delicious with private group food tour experiences available all season long.

Bundle up and follow one of our friendly local guides through one of Boston’s tastiest neighborhoods on a festive Happy Hour Stroll, a Classic Boston Tour complete with warming chowder, or a Chinatown adventure featuring steaming, cozy soup dumplings. It’s the perfect way to add a little cheer, connection, and comfort to your winter calendar.

Classic Afternoon Tea

Photo Credit: Trifecta

If you’re craving a cozy, elevated escape from the winter chill, treat yourself to afternoon tea at Trifecta — a Boston dining spot that’s perfect for a seasonal indulgence. Imagine sipping a warm, fragrant pot of tea and nibbling on elegant sandwiches and pastries while the winter light filters softly through charming windows. To make the experience extra festive (and extra jolly), don’t miss their signature tea cocktail — a merry mix of holiday flavors that pairs beautifully with scones or petit-fours. It’s a wonderfully warm, slightly indulgent way to slow down, savor the season, and add a touch of holiday cheer to your winter itinerary.

Catch a Christmas Classic 

Photo Credit: Brattle Theater

A neighborhood institution in Coolidge Corner, the Brattle Theatre has been delighting film lovers since 1953. Known for showcasing the best in classic, cutting-edge, foreign, and art-house cinema, the Brattle also screens first-run titles and new releases of beloved favorites. Their specialty, though, is their curated repertory programming — themed series that spotlight a director, genre, or subject over the course of a week or on select days throughout the month. This winter, tuck away the small screens and enjoy some true big-screen magic. The Brattle will be showing holiday classics all season long.

Cocktails in a Rooftop Igloo 

Photo Credit: Envoy

Dine and drink under the winter stars at The Envoy Hotel in the Seaport, where cozy rooftop igloos create a one-of-a-kind outdoor dining experience. Perfect for celebrating a special occasion or catching up with friends and family, each igloo offers panoramic views of the Boston skyline and waterfront while keeping you warm and comfortable. Indulge in seasonal fare and sip on festive cocktails like the Holiday Cruise, warm mulled wine, or a round of “Ho Ho Ovo” shots.

Visit a Winter Oasis

Photo Credit: View Boston

Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must on your holiday to-do list. The winter oasis features an array of holiday inspired cocktails, small bites, and unforgettable views of the city! Access to the winter oasis is granted on a first come, first served basis.

Catch a Bruins Practice

Photo Credit: Boston Bruins

If you want to see the Bs play but don’t want to spring for the pricey tickets, or if you just want to get a fresh perspective on watching this powerhouse team, then head to Warrior Ice Arena at Boston Landing to catch a practice. The Bruins practices are open to the public and their schedule is posted on the Warrior Ice Arena website. It’s crazy how close you can get to the players, for FREE. It’s a lot of fun watching them joke around with each other and have some fun at practice.

Savor Homemade Bombolotti

Photo Credit: Cantina Italiana

A must on any list of things to do in Boston in the winter is indulging in a warm bowl of homemade bombolotti with lobster, the signature dish at Cantina Italiana in Boston’s historic North End. Made fresh in-house with their special pasta machine, each perfectly crafted noodle soaks up the rich, buttery lobster sauce for an indulgent, soul-warming meal. This ultimate winter comfort food blends Italian tradition with a touch of luxury — a must-try for food lovers looking to savor the season in Boston.

Frostbite Sailing on Boston Harbor

Photo Credit: Boston Sailing Center

Okay, we know this might sound a little outrageous, but we couldn’t resist including it on our list of things to do in Boston in the winter — mostly because it actually exists and, honestly, we’re impressed that people really do it. Frostbite Sailing with the Boston Sailing Center offers adventurous souls the chance to brave the chilly waters of Boston Harbor for a truly unique winter experience. Whether you see it as comic relief or an unforgettable winter activity, Frostbite Sailing is ready and waiting for anyone brave enough to participate!

Crack Open a Book!

Photo Credit: Parkside

When the winter chill sets in, one of the coziest things to do in Boston in the winter is curling up with a good book — and Parkside Bookshop in the South End is the perfect spot to do just that. One of our favorite bookstores in the city, Parkside is a welcoming haven for readers of all tastes. Be sure to explore their huge collection of local cookbooks, perfect for finding inspiration for your next culinary adventure. Whether you’re browsing for a classic novel, a new bestseller, or a cookbook to spark some kitchen creativity, Parkside Bookshop is a must-visit stop on a winter day in Boston.

Drink Loaded Hot Chocolate

Photo Credit: savemeabite_ and fatcactusboston

When winter calls for something decadent and over-the-top, you’ve got to try the hot chocolate from Fat Cactus at Snowport. This isn’t your average cocoa — it’s a towering indulgence, piled high with whipped cream, gooey marshmallows, drizzled chocolate, and all the cozy comforts you crave after a chilly day. To make it even more irresistible, each cup has a Tuck’s truffle at the bottom, melting into the rich chocolate for an extra burst of sweetness. Perfect for sharing… or not. Whether you’re wrapping up a day of sightseeing or just treating yourself, this loaded hot chocolate is a deliciously outrageous, must-try winter indulgence made just for Boston’s cold months.

Take a Cheese & Wine Class 

Photo Credit: Formaggio Kitchen

One of our favorite spots for all things cheese, wine and beyond, Formaggio Kitchen South End, offers in-person classes that cover everything from the basics to cheese caves, food and drink pairings, and the cuisine of different regions around the globe. They’re also a stop on our South End Tours, making them one of the best things to do in Boston in the winter. It’s the perfect way to warm up on a chilly day with a hands-on, delicious experience that’s sure to lift your spirits.

Visit a Local Distillery

Photo Credit: Boston Harbor Distillery

There’s nothing better to warm you up during the frigid winter months then a glass of whiskey. It’s a fact that we can’t refute. Boston Harbor Distillery is the ideal place to spend an afternoon warming up. Visit their cabin-like cocktail bar filled with a wood and brick interior to enjoy some spirits with your friends or family. To make them even more “Bahston,” they have a line of spirits distilled from Sam Adams beer.

Go Ice Skating in the Park

Photo Credit: Boston Common Frog Pond

One of Boston’s most classic winter activities is skating on the Boston Common Frog Pond. It’s pretty magical ice skating outside in the middle of Back Bay. Forget you’re cold and focus on amping up your stopping game, we all know this is the hardest part of skating, but you got this!

Visit Museums!

Photo Credit: Isabella Stewart Gardner Museum

What is the perfect way to get some walking in and enjoy the great indoors? A museum day of course! Lucky for you Boston has tons of museums to offer. A few of our favorites are: the Museum of Science, the Museum of Fine Arts, and the Isabella Stewart Gardner Museum. Make a day of it and take your time enjoying things you might not have noticed.

Head to the Tropics

Photo Credit: Shore Leave

This local favorite is the perfect tropical haven to escape frigid winter days and nights. Shore Leave will help you forget dreary New England winters with cocktails that remind you of feet in the sand and sun on your skin. A true tropical oasis in the South End, head in for sushi, burgers, hot dogs, and tropical drinks. And for the month of December, Shore Leave transforms into a magical holiday haven, adding festive cheer to their already vibrant atmosphere. Winter blues, be gone.

Visit Boston Public Market

Photo Credit: ArchDaily

Boston Public Market is a mecca for local, specialty foods of all kinds. They have bagels and doughnuts and coffee and artisan s’mores and more. Oh, you want to hear more? Okay. They have fresh pasta and fudge and vegetables and juice and seafood…and more. You’ll just have to go and see for yourself! You could easily spend an entire afternoon eating your way through the market. And we proudly admit that we have before.

Play, Drink & Be Merry

Photo Credit: Versus

This hip arcade/restaurant/bar has been the place to be for a night of fun since it opened its doors not too long ago. Old school arcade games line the walls flashing their lights and accentuating the pop-art all over. The interior is inspired by 80s pop culture and the cocktail menu has a fun game-inspired spin to it. Try out their Reboot Bellini or their Joystick Julep for example. Game over.

Sinatra Sunday

Photo Credit: Cappo

Warm  up on Sunday evenings at Cappo in Southie. They are offering a Sinatra Sunday Dinner Show featuring Rich DiMare and the Ron Poster Trio every Sunday. Doors open at 5 pm. so you can enjoy live music from 6-9 pm along with a hearty Italian Sunday dinner. They have 15 stage-front tables available for dinner reservations, with the full menu available so be sure to book ahead and reserve your spot.

Play Curling

Photo Credit: The Liberty Hotel

Winter doesn’t stop the fun at The Liberty Hotel, Boston’s iconic former jail turned luxury hotel! Try your hand at curling on their private patio for its mix of strategy and skill. The curling package ($180 for up to 6 people) includes 45 minutes on the rink, a scoring card with instructions, and a sweet & savory box of treats. With lighter synthetic stones, it’s perfect for beginners and curling fans alike. Curling runs all winter long, so grab some friends, sip cocktails, and enjoy this unique Boston winter experience!

Soju Roulette

Take a gamble that is definitely going to play out in your favor with the Soju Roulette at Double Chin in Boston’s Chinatown. One of our favorite places to eat and drink in the city, this modern Hong Kong-style restaurant was founded by the Chin sisters, Emily and Gloria. Located in the heart of Boston’s Chinatown, they specialize in Chinese dishes with modern twists and fun cocktails that you won’t see anywhere else, like the Soju Roulette – two rounds of eight shots including their original, mango, strawberry, peach, lychee, and green apple flavors. Cheers to winter. You’re guaranteed to warm up real fast here!

S’mores On a Rooftop

Photo Credit: Intercontinental

Craving a sweet winter night out? Head to the rooftop at InterContinental Boston for their indulgent s’mores package — one of the coziest things to do in Boston in the winter. Nestle by the fire with your crew, roast marshmallows over the glow, and build the perfect s’more. Pair it with a hot drink or a winter cocktail, and enjoy city‑scape views that make the moment even sweeter. Whether you’re wrapping up a long day or simply want a festive treat with friends or loved ones, this rooftop s’mores session is a delightful winter escape high above downtown Boston.

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