Things to Do in Boston This Winter

Joseph Coupal - Thursday, January 09, 2020
Lallis & Higgins Insurance, Quincy, Weymouth, MA

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 Sunday. 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 #11). *wink*

24. Snowflake Afternoon Tea at The Langham Hotel

Cozy up around an elegantly set table at The Langham Hotel for a wintery spin on the classic afternoon tea. Their snowflake tea menu includes tea sandwiches, cream scones with jam, and an assortment of pastries that have been kissed by the winter season, and of course a pot of tea too. We’ve got our eyes on the hot chocolate pot de crème with toasted marshmallow. Don’t mind if we do.

23. Private Food Tour with Bites of Boston

Just because tour season is technically on pause doesn’t mean the rules can’t be bent just a little. 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!

Note: Regularly scheduled neighborhood food tours in the South End, Allston, and Chinatown will start again in March.

22. Visit Bow Market

Bow market is the new hot spot in Somerville attracting people all throughout the year. 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.

21. See a Film at Brattle Theatre

A neighborhood institution in Harvard Square, the Brattle Theatre has been showing films since 1953. According to them: 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.

20. Have Hot Chocolate at LA Burdick

Let’s be real. Winter is allllll about the hot chocolate. All day every day. L.A. Burdick is the perfect getaway from the frigid winter temperatures. Sit inside and savor the best hot chocolate you will ever taste. It is thick and rich and full of flavor. They offer various chocolate varieties from different countries that all have unique flavor profiles – just like coffee does.

19. Watch the Boston Bruins Practice at Warrior Ice Arena

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.

18. Frostbite Sailing on Boston Harbor

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.

17. Take a Yoga Class at a Brewery

One of our favorite winter activities is mixing our fitness with booze. Need we say more? Warm your heart with brewery yoga, being offered by many local Boston breweries this winter. You can find a list of breweries offering yoga on Eventbrite; and most classes include one beer in their ticket price. Nama-stay-thirsty.

16. Taza Chocolate Factory Tour

Taza is a local chocolate company based out of Somerville. 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 Kitchen Class at Formaggio Kitchen

Visit one of of our favorite spots this winter for a kitchen class where you’ll have the chance to learn about all types of things culinary from cheese caves to food and drink pairings to the cuisine of different regions around the globe. Formaggio Kitchen 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.

14. See a Comedy Show at ImprovBoston

Knock, knock.
Who’s there?
Jokes…that are a lot better then this one.

Visit ImprovBoston for a show. Everyone could use some laughter in their day! And clearly we’re not the ones with the jokes. We’ll stick to food.

13. Visit 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.

12. Go Ice Skating on the 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!

11. Have the Hot Chocolate Flight at Met Back Bay

This piece de resistance is the Boston Hot Chocolate Experience being offered at Met Back Bay. Four luxurious, flavored hot chocolates make up this flight. But wait. There’s more. You can get them SPIKED, making them a true flight. Each flavor has an “adult” upgrade to warm the heart and soul. Go ahead, you deserve it. We’ll see you there!

10. Shop/Eat at The Prudential Center

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….

9. Visit the Skywalk Observatory

For a beautiful, one-of-a-kind view of Boston visit the Skywalk Observatory, conveniently located on the top of the Prudential Center, so while you’re there shopping stop up. You can see “Boston’s past, present, and future” from there as this is also the location of the Dreams of Freedom Museum. The full experience gives visitors an appreciation for Boston’s storied past, its remarkable architecture, and its rich global culture.

8. Have a LARGE Cocktail with Your Friends at Fat Baby

What’s the go-to activity when it’s cold outside? DRINK! At least that’s what it is in Boston. So many restaurants have fun large format cocktails to share with your friends but the one that has especially caught our eye as of late is Fat Baby in South Boston, “Southie” to the locals. Try their rotating Polynesian Punch or one of their other specially crafted drinks and you’ll be warm in no time.

7. Visit Museums!

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.

6. Visit Boston Public Market

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.

5. Take a Cooking Class with Cozymeal

Instead of spending money on a dinner out this winter try learning how to make a great meal yourself. Even if you’re a top-notch home chef, taking a class with a friend or significant other can be a fun way to mix things up. Cozymeal offers a huge variety of cooking classes for you to choose from for groups of all sizes. You can have the class at the chef’s pre-approved place or have them come to you. These experiences are very customizable and guaranteed to be a great time with a delicious ending!

4. Visit Branch Line’s Beer Hall on Wednesday Nights

Branch Line won’t let the freeze stop their fun so go ahead and join them! Every Wednesday night they transform their year-round covered, heated patio into a classic, German beer hall. Head over for some bites and brews and forget about what the weather is doing outside.

3. Eat Boston Classics at Beantown Pub

If you’re looking for a winter activity in Boston then why not keep it classic and head to Beantown Pub for some Boston baked beans and brown bread to comfort you. History is pouring out of this place from the molasses in the beans and bread to it’s location right on the Freedom Trail in historic downtown.

2. Play Games, Eat, and Drink at 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.

1. Have Drinks at the Igloo Bar at the Envoy Hotel

For you winter extremists head to The Envoy Hotel and sip some drinks in your own personal rooftop igloo overlooking Boston’s skyline and harbor. This is a unique and exclusive experience that you don’t want to miss. Arrive early since the six, heated igloos are usually given out on a first come, first serve basis. It’s open from Wednesday through Saturday from 4 to 11pm. Talk about making the best of winter in Boston. You are for sure #winninginwinter if you do this!


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