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

January 8, 2022 | , , , ,
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Things to Do in Boston This Winter

Yes folks, it’s officially winter. We’re sure you got the memo as you dug your car out of a pile of snow in sub-zero temperatures the other day, but in case you didn’t we had our first big snowstorm of the season on Friday. We know you want to hunker down at home and hibernate for the season (we do too) but if you find yourself a tourist here in winter or a local getting a little stir-crazy and looking for some fun activities to keep you occupied in Beantown then we’ve got you covered. There are plenty of things to do in Boston during the winter so you better get cracking on this list!

Bundle up and remember that hot chocolate makes everything better, before, during, or after any of these activities. Or all three. Especially when it’s spiked (see #12). *wink*

25. Bootcamp and Brews at Idle Hands


Photo Credit: Idle Hands

This popular event is back at Idle Hands to help warm you up this winter in Boston! Warrior Fitness is taking over the tap room at Idle Hands Craft Ales with a high intensity, bootcamp style workout on several Sundays throughout winter. Join them for a 60-minute total body blast that will include: stretching, three circuits, an ab finisher, and a cool down. Then, hang with them afterwards for 2 5-oz Idle Hands beer samples and games. Sunday funday at its finest.

24. Afternoon Tea at Trifecta

afternoon tea

Photo Credit: Four Seasons Boston

Warm up this winter with a spot of afternoon tea at the Four Seasons Hotel One Dalton Street. They serve a lovely, contemporary take on the classic afternoon tea at their restaruant, Trifecta. The Afternoon Tea features eclectic tea sandwiches, freshly baked scones, unique sweets and bespoke blends of local favourite J’enway Tea Co. If you’re really feeling like warming up this winter in Boston, go for the spiked tea option! Trifecta’s in-house mixologists artfully pair each tea with a liqueur or spirit to elevate the flavour, based on the tea selection and flavour profile. Some of the favourites include Lady Blue Earl Grey Tea paired with Grand Marnier; Champagne & Berries Tea paired with St-Germain; Fruity Pebble Tea with Luxardo liqueur and Calming Chamomile Tea with crème de violette. Why haven’t we been spiking our tea all along?? Trifecta Afternoon Tea is offered on Saturdays and Sundays from 11:00 am to 3:00 pm. Cherio!

23. Private Food Tour with Bites of Boston

Just because our public food tour season is on pause until the spring, doesn’t mean we can’t still have a little food and fun together! Bites of Boston Food Tours is available to host private group food tour experiences for your group during the winter. Bundle up and enjoy a visit to one of Boston’s most tasty neighborhoods in the company of a knowledgeable and friendly local guide – a great idea for a family fun day, company outing, or other celebration!

22. Drink Coffee by a Fire Pit at Bow Market

fire pit

Photo Credit: Bow Market

Bow market is a hot spot (pun intended) in Somerville to shop, eat, and chill by a fire pit! This public courtyard in the heart of Union Square used to be a storage building but is now comprised of over 30 independent food, art, and retail shops. Come support these artesian vendors and fill your belly and bags with all the amazing things they have to offer. But, don’t forget to warm up with a warm drink by one of the fire pits. New England winter at its finest.

21. Eat Clam Chowder at Boston Chowda Co!

This may seem like an obvious one for New Englanders but it’s a DEFINITE for winter warming up. There’s truly nothing like a cold-nosed, chilly day with a steaming cup of chowder in hand. Head to Quincy Market for what we think is Boston’s best chowder at Boston Chowda Co. and kiss the winter blues goodbye one spoonful at a time.

20. See a Film at Brattle Theatre

outside brattle theater

Photo Credit: @grrlhauscinema via Instagram

A neighborhood institution in Harvard Square, the Brattle Theatre has been showing films since 1953. The Brattle shows the best in classic, cutting-edge, foreign, and art-house films. They also show first-run films and new releases of classic films, but their specialty is a repertory programming format consisting of films from a particular director, genre, or subject shown over the course of a week, or on the same weekday throughout the month. Put away the small screens to get some big screen time this winter.

19. Book an Igloo at Woods Hill Pier 4 for Dinner & Drinks!


Photo Credit: Woods Hill

Dine and drink underneath the winter starts at Woods Hill Pier 4 in the Seaport in one of their heated igloos! They have created a memorable experience to dine outdoors in cool weather, in a socially distanced, safe and private environment. Whether you are celebrating a special occasion or catching up with friends and family, each of their igloos offer beautiful panoramic views of the Boston skyline. While you stay cozy inside, they will serve you their delectable farm to table cuisine, creative cocktails, and carefully curated wines. May we suggest the warm spiked cider!

18. Watch the Boston Bruins Practice at Warrior Ice Arena

bruin player going onto ice

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.

17. Frostbite Sailing on Boston Harbor

sail boats on water

Photo Credit: Boston Sailing Center

Okay, so we think this is outrageous too. But there is something for everyone and we couldn’t resist including this on the list merely because it exists and we are impressed that people actually do this. Whether you consider this a bit of comic relief or a great suggestion for a winter activity, know that Frostbite Sailing exists on Boston Harbor and is there for you if you want to participate.

16. Taza Chocolate Factory Tour

taza chocolate

Photo Credit: Taza Chocolate Factory

Taza is a local chocolate company based out of Somerville that we LOVE! They make chocolate the old fashioned stone ground way, and it’s goooooood. The texture is slightly gritty but that gives it character, and the taste is incredible. This is as close to Willy Wonka and the Chocolate Factory as you can get here in Boston so go ahead and take their factory tour to escape the winter chill!

15. Take a (Virtual) Kitchen Class at Formaggio Kitchen

formaggio staff with cheese

Photo Credit: Formaggio Kitchen

One of our favorite spots for cheese and culinary classes, Formaggio Kitchen, has taken their curriculum virtual! They will teach you everything from the basics to cheese caves to food and drink pairings to the cuisine of different regions around the globe. Formaggio Kitchen South End is a stop on our Sweet & Savory South End Tour and they are the perfect place to head for a winter blues pick-me-up that doesn’t require you to even put real clothes on.

14. Visit Boston Harbor Distillery

outside boston harbor 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.

13. Go Ice Skating on the Boston Common Frog Pond


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!

12. Drink Bourbon Hot Chocolate at Buttermilk & Bourbon!

spiked hot chocolate

Photo Credit: Buttermilk & Bourbon

Winter is for cozying up with hot chocolate there’s no doubt about that. BUT, Buttermilk & Bourbon is taking it one step further and spiking their mugs of rich hot chocolate with…you guesses it…BOURBON. We’ll gladly get snowed in any day with this treat. head to either their Boston or Watertown locations to enjoy this cup of pure winter joy.

11. Shop/Eat at The Prudential Center

outside prudential center

Photo Credit: @lukemacneil92 via Instagram

The Prudential Center, which most Bostonites refer to as the “Pru,” is a shopping haven full of retail stores and restaurants. It’s also home to Eataly, the Italian dining destination that will keep your senses stimulated. You can shop ’til you drop, refuel, and keep going without even having to leave the building and freeze. It’s easy to spend hours and hours in here. Trust us….

10. Visit Museums!

inside isabella stewart gardner museum

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.

9. Head to the Tropics at Shore Leave


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. Winter blues, be gone.

8. Visit Boston Public Market

inside 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.

7. Play Games, Eat, and Drink at Versus 

inside arcade

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.

6. Experience the Imagine Van Gogh Exhibition at the SoWa Power Station

van gogh exhibit

Photo Credit: SoWa

The SoWa Power Station in an iconic masterpiece of late-industrial glamour. Built in 1891 as the world’s largest power generation plant, it produced enough electricity to run the West End Street Railway. The century-old property’s structural elements have since been rescued and restored, transforming it into a blank canvas for community, celebration, and innovation. Right now it is the host to the Imagine Van Gogh Exhibit, an immersive exhibition featuring more than 200 of the Dutch artist’s paintings, and will be through March. The exhibit brings Van Gogh’s canvases to life in a vivid and spectacular way, transporting you off the chilly streets of Boston to another place completely.

5. Enjoy A Sinatra Sunday Dinner Show at Cappo


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.

4. Take an Online Cooking Class with Milk Street Kitchen

Founded by Christopher Kimball, Milk Street Kitchen is a culinary hub in Boston offering cooking classes and workshops, a magazine, podcast, and tv and radio shows. The space was inspired by Kimball’s travels and the idea that ethnic cooking is just dinner somewhere else in the world. At the Milk Street Online Cooking School you can join them for live streaming classes or take any of their free, self-paced pre-recorded lessons. In both virtual classrooms, you won’t learn just recipes: you’ll learn new ways to approach food and cooking, giving you a reinvigorated enthusiasm for putting dinner on the table. What better time to sharpen your culinary skills then the cold days of winter?!

3. Play Curling at The Liberty Hotel


Photo Credit: The Liberty Hotel

Back again is Curling at The Liberty Hotel! You can once again throw stones at Beacon Hill’s Liberty Hotel. Curling stones, that is. Join them for a winter curling experience at The Liberty’s private patio, The Yard, every Saturday and Sunday from December through March. Enjoy curling on their synthetic rink, cocktails, and light bites. Make sure to book ahead and your pre-paid package includes: 45 Minutes of Independent Curling on their Synthetic Rink (up to 6 players), Scoring Card with Playing Instructions, Carafe of Dutch Hot Chocolate, 4 ”Buzzy’s” Beef Sliders | Wagyu Beef with Great Hill Blue Cheese on Toasted Brioche with Spicy Aioli and 4 Just Baked Chocolate Chip Cookies. The ”Buzzy’s” Beef Sliders are inspired by The Liberty’s rich history as the Charles Street Jail. They are a nod to Buzzy’s Roast Beef stand, which was located adjacent to the jail, and where generous patrons would often toss the prisoners sandwiches over the wall. We love a Boston bite with a side of history!

2. Take A Candle Making Class with Noted.

candle making

Photo Credit: Noted.

Join Noted. at the Local Maker Studio in South Boston for a Candle Making Class, hosted by Ashley the owner of Noted. Each person will choose the style and fragrance for their candle which you will then make from scratch. To round out your set, you will also customize one of their Match Bottles! They offer a complementary glass of wine for class, to everyone 21+ of course. This is a great way to warm up with friends and make something that you can enjoy throughout the winter season. The fee includes all your class materials and return shipping to get your candles to you after class, they will not be ready to go home with you at the end of the session. You can also book a private class for you and your friends to have s more intimate experience.

1. Enjoy Soju Roulette at Double Chin

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!

Editor’s Note: This post was originally published on January 19th, 2018 and has been updated and revamped for accuracy and fresh content.

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