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Top 6 activities to Do in Boston in the Winter

5 minute read
Top 6 activities to do in Boston in the Winter

One of the best things about living in Boston is experiencing all four seasons to their fullest. Of course, during arctic blasts and other extreme winter conditions, experiencing winter to the fullest doesn’t always seem like such a great idea.

Respectfully, we beg to differ. From playing in the snow to cozying up indoors, winter is one of the best times to live in Boston. The city is beautiful, and it’s difficult to explain the joy of a warm drink by the fire to someone who thinks that 40 degrees Farhenheit is a cold front. So whether you’re braving the winter wonderland, or staying indoors, here are five of the best things to do in Boston in the winter.

This isn’t a ranked list: just a collection of our favorite things to do in Boston when it’s snowing. So bundle up, and come along!

Head to Boston Common for Snowy Outdoors Fun

Boston Common is a great spot year-round, but falling snow brings out some uniquely wintery good times. Locals, visitors, and suburbians flock to the Common to play in the picturesque winter wonderland.

Go Ice Skating at Boston Commons Frog Pond Ice Rink

Go Ice Skating at Boston Common’s Frog Pond

An iconic winter tradition in The Hub, gliding across the frozen Boston Common Frog Pond earns its classic status anew every year from December to March. Skaters under 58 inches get in for free, and it’s only $5 otherwise. Skate rentals are $10 for adult sizes and half of that for children’s skates, making this a decidedly cost-effective winter activity.

There really is something magical about the scene: especially as the sun goes down and the city lights up. Living in Back Bay frequently feels like a scene from a movie sprung to life, but nighttime skating under strings of lights might as well be from a holiday special or romantic comedy, where you and Boston share top billing.

Sledding on Boston Common’s Flagstaff HIll

Go Sledding on Boston Common’s Flagstaff Hill

A big Boston reliably means two things: hunkering down with hot chocolate, for one. But the next day, kids and adults alike make their way up Flagstaff Hill to play on the snow-covered slopes. Nothing brings back the pure nostalgic joy of childhood like whooshing down a snowy hill at speeds that feel much faster than they actually are.

Flagstaff Hill is a popular spot, which makes it feel lively and vibrant: kind of like a sled party. But if you’re feeling crowded, or simply want to try some different hills, South Boston’s Marine Park and the South End’s Titus Sparrow Park might be less well-known but offer seriously great downhill action.

Food and Brewery Tours

Boston has a great food and drink scene, and if it’s too cold to run around outside, there’s a wide range of excellent seasonal fare available, and some fun activities to be had besides. For example:

Blend Fitness and Fun with Yoga at a Brewery in Boston

Blend Fitness and Fun with Yoga at a Brewery

Really, the title says it all. Mix your personal fitness with the craft beer scene by taking a yoga class at a local brewery. While locations like Lamplighter Brewing and the Remnant Brewing Company are outside the city — but still in Greater Boston, located in Cambridge and Somerville respectively — places like Democracy Brewing and Backlash Beer Company offer this uniquely modern twist on some of our hip favorites. Check Eventbrite for an easy list of locations and ticket prices.

Head to Taza Chocolate for “You and the Chocolate Factory”

Head to Taza Chocolate for “You and the Chocolate Factory”

While there might not be any Oompa-Loompas on staff, a tour through Somerville’s Taza Chocolate is basically like getting to see Willy Wonka’s factory in real life (with, you know, much better safety standards).

Want to see old-school, stone-ground chocolate being made? Eight bucks gets you in for a 45 minute to 1-hour tour, complete with samples of their organic, Mexican-style dark chocolate. Plus, 1$ of your admission fee goes to the Museum of Science to support education in the greater Boston metropolis. Coming with kids under 10 years old? Swing by at 10:30 in the morning most weekends for Taza Cacao Scout Bingo ($6) or Chocolate Story Time (free!) are sure to be a hit.

Catch Seasonal Events Around Boston

Everything we’ve covered so far works regardless of schedule: weather permitting, of course. But Boston also has plenty of great seasonal events worth taking in.

Visit the Annual Boston Tea Party Reenactment

Every year on December 16th, the Boston Tea Party Ship holds a reenactment of the revolutionary act. Start at the Old South Meeting House, and march alongside 100+ re-enactors who bring the historic event to life. Educational and downright fun, we’re not afraid to spill the tea on this event: it’s easily one of the best things to do in Boston in the winter months.

Take in the Lights at a Tree-Lighting Ceremony

Take in the Lights at a Tree-Lighting Ceremony

All through December, tree-lighting ceremonies literally light up Boston’s winter nights. Head to Boston Common and see the special Nova Scotian tree light up as part of a festive event, while Macy’s, Copely Square, the Massachusetts State House, Public Garden, and of course, the Big Tree lighting ceremony and Blink! light show at Faneuil Hall Marketplace each make for a magical winter evening.

And while it doesn’t involve a Christmas tree per se, the Christopher Columbus Park trellis lighting ceremony is routinely one of the best things to do in Boston in the winter.

Boston is a Winter Wonderland

So there you have it! Six of the best things to do in Boston in the winter. Honestly, this list could be ten times the length, and we still wouldn’t have covered all of the best winter activities in Greater Boston, so if you have any activities to add, please share your thoughts! Whether we left your favorite off the list, you want to share your experience with any of the above, or just have your own winter tips to share, let us know what you think the best things to do in Boston in the winter are!

Demetrios Salpoglou

Demetrios Salpoglou

Published December 5, 2019

Demetrios Salpoglou is the CEO of which is an information and technology based services company that provides cutting edge resources to real estate companies. Demetrios has developed over 90 real estate related websites and owns hundreds of domain names. Demetrios also owns and operates six leading real estate offices with over 120 agents.

Demetrios has pulled together the largest apartment leasing team in the Greater Boston Area and is responsible for procuring more apartment rentals than anyone in New England – with over 130k people finding their housing through his services. Demetrios is an avid real estate developer, peak performance trainer, educator, guest lecturer and motivational speaker.