Boston winter vacation

Have you ever wondered what to do in Boston over winter vacation? People from all over who are thinking of spending their winter vacation in Boston have you covered. We present to you the best ways to spend your winter vacation in Boston.

Sometimes, the best way to beat the winter blues is to escape the cold and soak up some sun with a winter vacation to Boston. Sure, NYC may have Broadway and Central Park, but Boston offers so much more — New England charm, vistas of the Boston Harbor, and delicious cuisine. I’ve created this guide based on firsthand experience living in Boston as a resident myself (not to mention I also work here during summers!). If you are thinking about planning your own trip to Beantown or want tips on where to experience everything it has to offer its visitors, you will want to read this guide.

Winter vacation in Boston is the perfect way to escape the cold and snow. With a variety of activities, you’ll never be bored while visiting this historic city.

If you’re looking for something more adventurous, head to Sky Zone Boston for an indoor trampoline park that will keep you busy all day long! Located right by Fenway Park, Sky Zone is sure to impress even the most avid sports fan. The facility offers birthday parties and other special events as well as open jump times for kids and adults alike.

If you’re looking for something more sedate, visit the Museum of Fine Arts Boston. This museum features nearly 250 galleries that showcase over 450,000 works of art from around the world. The museum has several special exhibits each year and hosts many lectures and events throughout the year as well.

Boston’s most popular restaurant is unquestionably Legal Sea Foods with locations throughout New England including one at Logan International Airport (BOS). The menu features award-winning seafood dishes such as broiled lobster tails as well as a variety of pasta dishes such as linguine with clams or mussels marinara served with garlic breadsticks and salad dressing on request. If you don’t see what

If you’re looking for a winter vacation that’s both serene and exciting, Boston is the place to be.

Boston is full of history, art, and culture. You can explore the city’s many museums, including the Museum of Fine Arts and the Isabella Stewart Gardner Museum. Or check out the famous Boston Common, where you’ll find a number of local vendors selling everything from souvenirs to delicious food.

If you’re looking for something more active, there are plenty of activities available in Boston as well: visit one of the city’s many parks or take an ice skating lesson at Frog Pond in Harvard Square.

The weather in Boston is typically cold during winter months (December-March), with temperatures averaging around 35 degrees Fahrenheit (-1 Celsius). But there’s no need to let that stop you from visiting! With so many indoor attractions like museums and shopping centers available throughout the city, there are plenty of things to do even when it’s cold outside!

WINTER IN BOSTON FAQ’S

You probably have plenty of questions about visiting Boston in the winter. Like, yes, we know it’s cold! But how cold is it? Will my hands freeze off?

Well, I’ve got all the answers you need to plan your trip.

HOW COLD IS BOSTON IN THE WINTER?

I’ll be blunt: Boston gets pretty freakin’ cold in the winter. The average temperature hovers somewhere around 37 degrees Fahrenheit in December, 30 in January, and 33 in February.

But the winter weather is all part of its charm, and a fresh coating of snow (which can happen as early as October) adds another layer of magic to the whole winter experience.

To see the city at its best, I suggest planning your visit for December. It is *slightly* warmer than the rest of the winter, and the holiday season means that trees are draped with twinkly lights, festive events abound, and as much cheer as we stoic, reserved, slightly gruff Bostonians can muster is in the air.

An equestrian statue of George Washington at the Public Garden covered with snow at sunrise in Boston
George Washington plows forward in the snow of Boston Public Garden, and you can too! Boston is incredibly walkable all year round.

HOW DO I GET AROUND BOSTON?

Boston is incredibly walkable — and also has a solid public transportation system that includes a subway (known as “The T,” short for MBTA), buses, and commuter rail trains — so no worries if you don’t have a car. Plus, unlike the overwhelming behemoth that is New York City’s transit system, ours is quite like Boston itself: small and cute.

In fact, it’s much easier to get around here in the winter without a car, since you don’t have to deal with the stress of parking between snowbanks and dealing with the city’s notoriously tricky and confusing streets.

We have five main subway lines designated by colors — green, red, orange, blue, and silver — which will get you just about anywhere you want to go in Boston proper and beyond to the suburbs of Newton, Brookline, Cambridge, Somerville, Malden, and Revere.

  • Word to the wise: if you’re used to cities with logically numbered streets and grid layouts that are easy to navigate, you might be in for a bit of a shock, because Boston has neither. In fact, it seems to actively discourage any kind of sense-making or logic when it comes to its roadways. One-way streets, streets that change names halfway down, streets that abruptly end…they’re all par for the course here, and it’s not uncommon for natives to still get lost once in a while. It’s just one of the many charming quirks of this special city (and another reason to forego the car if you can).

WHAT IS BOSTON KNOWN FOR?

Boston is known mainly for two things: its colonial history and its sports. While strolling through its most famous public park, Boston Common, it’s not, um, uncommon to spot a costumed Ben Franklin scrolling on his iPhone in between guided tours, or to find yourself smack-dab in the middle of a Red Sox victory parade.

However, the city’s beginnings actually date back to around 2400 B.C., when the Massachusett Tribe of Native Americans lived here, dubbing the land Shawmut, meaning “place of clear waters”.

Fast forward to the 1630s, when the Puritans arrived and much of the Boston we know today began forming. Then came the Boston Massacre in 1770, the Boston Tea Party in 1773, and the Revolutionary War in 1775, all key events in both the country and city’s story.

While it may lack the year-round temperate weather of southern and western U.S. states, the city’s colorful fall foliage, spring blooms, idyllic New England summer atmosphere, and — of course — enchanting winter scenery gives visitors something to look forward to at any time of the year.

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A sunny snowy day at Copley Square looking out toward the Boston Public Library and Old South Church in Boston
A sunny snowy day at Copley Square looking out toward the Boston Public Library and Old South Church in Boston. Boston is known for its deep, rich history! Photo Credit

THINGS TO DO IN BOSTON IN THE WINTER

Being in Boston in the winter doesn’t mean you have to stay inside the whole time; in fact, I strongly discourage it!

There are plenty of fun activities outside in the frosty brilliance of the snow to keep you occupied, and with the right attitude — and the right warm clothing (see below!) — you’ll have a cool time in even the coldest of weather here.

The exterior of Quincy Market with holidays lights and a Christmas Tree along the street at night in Boston
The annual holiday lights in front of Fanueil Hall and Quincy Market are truly epic! Photo Credit

SEE ALL OF THE HOLIDAY LIGHTS

There’s just something about holiday lights; no matter how many times you see them, they get you right into the spirit of the season during the long winter nights. Here are the best spots to light-peep:

TREE LIGHTINGS

If you’re lucky enough to find yourself in Boston in December, you might just have the chance to see one of several holiday tree lightings. There’s caroling, plenty of Christmas cheer, and despite the cold temperatures, the energy is as warm and fuzzy as can be, giving the city a very small town Gilmore Girls feel.

  • Boston Common Tree Lighting: The biggest tree lighting takes place in early December at Boston Common, and usually features local — and sometimes national — singers and theater performers, fun activities, yummy food, and hot beverages. Plus, of course, the pièce de résistance: a massive tree, given as a gift each year from the Province of Nova Scotia, that’s dressed to the nines in bright, vibrant multicolored lights. Once the switch is flipped, that is.
  • Copley Square Tree Lighting: Located in the beautiful Copley Square, with a large fountain overlooking Trinity Church, you can witness the lighting of the large, light-covered tree with refreshments and holiday giveaways! Don’t forget to look for holiday favorites like Santa and Rudolph while you listen to holiday music by the Boston Pops Brass Quintet!
  • Holiday Trellis Lighting at the Christopher Columbus Waterfton Park: While not a tree lighting per se, this lighting is still epic! Located along the waterfront, this 260-foot long trellis is illuminated with 50,000 blue bulbs in a very dramatic holiday display, along with lighted trees in the park itself. Besides the usual hot chocolate and cookies, they also offer the very-Boston clam chowder.
A Christmas tree lit up at night in front of an impressive clock tower in Boston
Blink! At Faneuil Hall is simply magical during the holiday season! Photo Credit

BLINK! AT FANEUIL HALL

Located at Faneuil Hall Marketplace, which features a large clock tower and columned marketplace from 1742, watching the light show here is like stepping back in time. Set to classical tunes by the Boston Pops, more than 350,000 white and colored bulbs on both the tree and the surrounding buildings pulse and flash to the music at random intervals.

The beginning of Blink! typically coincides with the tree lighting at Faneuil Hall around Thanksgiving, and you’ve never experienced a light show like this before. Blink! runs for six weeks, and is totally free to watch.

ILLUMINATIONS TOUR

The Illuminations Tour is a holiday light tour that takes you past the most decked-out holiday houses in Boston! I’m talking lawn reindeer, inflatable Santas, and yes, enough tacky Christmas lights to make you gasp in delight.

Local residents can add their house to a Google map, letting the general public come and gawk at their cheerfully gaudy creations…and then recoil in horror as they imagine their power bill.

Head to Somerville by subway, bus, Uber, or car to Somerville City Hall to hop on a 45-minute trolley tour (or take the self-guided driving tour)!

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Lots of people ice skating at sunset with twinkling lights at the Boston Common Frog Pond in Boston
Frog Pond Pavillon is the most popular and iconic place to skate in Boston. Watch people whoosh by and grab some hot chocolate after! (Photo Credit)

GO ICE SKATING

Contrary to popular belief, you don’t have to be a kid (or have kids) to go ice skating in Boston. Winter fun is for all ages here, so put lack up your skates and hit the ice, you fledgling figure skater, you!

  • Boston Common Frog Pond: Is it touristy? You bet. Is it a total blast? Also yes! Not only do you get the chance to skate in one of the most charming public parks in the country, but the possibilities for people watching are amazing even when you aren’t in the mood to show off your skills on the rink. The laughter of couples, families, and children fills the air along with the scent of goodies from the snack bar — don’t forget to grab a cup of coffee or cocoa after your skating session as you stroll through the Common and admire the (hopefully) snow-covered trees that frame the red-brick buildings of Beacon Street beyond the park.
  • Skate @ Canal District Kendall: For another option for your skating pleasure, check out Skate @ Canal District Kendall across the river in Cambridge. You can skake on this adorable oblong rink, surrounded by the modern Canal District buildings, the fairy lights of the surrounding trees reflecting in their windows. Afterwards, you can walk along the Charles River and watch Boston twilinking in the snowy twilight. Consessions and hot bevergaes available.
  • The Rink at 401 Park: This skating rink may be the hippest, and most “adult” feeling rink, nuzzled between Time Out Market and Trillum Brewing Company. This means that after skating in their super adorable and modern rink, you can grab food from the market in one of 15 eateriers AND grab a beer. They’re also sponsered by REI, which we love, so skating here is a true no-brainer!

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A canopy of twinkle lights at the SoWa Winter Festival with artisan stands in Boston
At the SoWa Winter Festival & Holiday Market, you can wander under dazzling lights and take in alllll the holiday cheer! (Photo Credit)

HIT UP THE HOLIDAY MARKETS

Whether you have some actual holiday shopping for friends and family to do, or you just want to soak up the lively atmosphere with a hot beverage in hand, make sure you get a taste of one of Boston’s winter markets.

  • SoWa Winter Festival & Holiday Market: SoWa (short for South of Washington St.) is a district in the South End that’s home to art galleries, a year-round vintage market, and an outdoor artisanal market in the spring and summer. In the winter, SoWa also shines with a winter festival that features seasonal cocktails and handmade gifts from local makers under a canopy of twinkling lights. It doesn’t get much more magical than browsing for unique holiday presents like candles, jewelry, and scarves with a spiked hot cocoa in hand, smelling the scent of fresh pine trees for sale- it’s always the perfect way to get into the spirit.
  • Holiday Market at Snowport: Once you’ve done your shopping, it’s time to play. Over in the Seaport, the relatively new Holiday Market at Snowport is a real-life oceanfront winter wonderland that will fulfill all of your festive fantasies with a Christmas tree market, freshly baked waffles, open-air electric sleigh rides, games like light-up bocce ball, and a 3,000-square-foot ice skating rink that also offers curling. If this doesn’t sound like some North Pole-realness, I don’t know what does!

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Lia drinking in a coffee shop in Boston wearing jeans and boots.
Actual footage of Lia in her natural habitat: drinking delicious coffee at Tatte in Boston. But let’s face it: in the winter, hot chocolate is far superior! Here’s where to get a hot mug of. itin Boston.

DRINK (AND EAT) DELICIOUS CHOCOLATE

What’s better than a steaming cup of hot chocolate on a chilly winter day? Really, tell me, because I can’t think of a single thing! Here are some of the best places to get some chocolate-y goodness to warm your soul:

  • L.A. Burdick: With two locations in Boston’s Back Bay and Cambridge’s Harvard Square, L.A. Burdick has some of the richest and best cocoa you’ll find anywhere, and I’m not exaggerating. In fact, they call “Drinking Chocolate” – because they’re fancy like that – and it’s so decadent and heavy that unless you’re seriously hardcore, order the small size and thank me later. 
  • Taza Chocolate Factory: True chocoholics can even take things a step further and check out a fully functioning factory to see how your favorite sweets are made at Taza Chocolate Factory in Somerville. Don’t worry; there won’t be any Willy Wonka weirdness here (well, hopefully) — just an informative and entertaining experience that obviously ends with chocolate samples. 

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