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17 Best Things to do in Boston in the Winter (a Local’s Guide)

17 Best Things to do in Boston in the Winter (a Local’s Guide)

17 Best Things to do in Boston in the Winter (a Local’s Guide)
Quaint, snowy cobblestone streets. Steaming cups of hot chocolate. Cheerful holiday lights. Find out about all the things you can do while visiting Boston during winter!

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Snowy cobblestone streets. Steaming cups of hot chocolate. Cheerful holiday lights. Boston in the winter is a snow-covered wonderland! Whether you’re taking a frosty afternoon walk on through one of Boston’s many quaint historic streets, ice skating on a frozen outdoor pond, or warming up with a bowl of New England clam chowder and a decadent mug of hot chocolate, there’s so much to do and see in Boston in winter.

Although I was born in Boston (and still have fond memories of building epic forts in the snow during the winter) we tapped a local to create this guide to all the best things to do in Boston in the winter. Take it away, Kim!

Psst: Looking for more New England travel ideas? Take a look at all of our travel guides for the East Coast, including these:

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Printable Winter Packing List

This FREE 3-page printable packing list will help make sure you don’t forget anything for your next winter trip. We’ll also send you our favorite travel tips!

The skyline of Boston at sunrise after the first snowfall of the year
Skyline of Boston with heaps of powdery snow. Now where’s my hot chocolate?

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.

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)!

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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Drink is a cocktail bar without a menu, you tell them what you like and they whip it up! What?! Genius! (Photo Credit: Xander Brown)

Warm up with Cocktails (and Comfort Food)

A day of sightseeing in frigid weather calls for an evening of snuggling up with a stiff drink at one of the many intimate, dimly-lit lounges in the city.

  • Lookout Rooftop Bar: For an especially unique winter experience, duck into one of the glowing igloos on the top of the Envoy Hotel in the Seaport to sip on Patron Old Fashioneds and snack on blistered shishito peppers. This swanky spot draws the see-and-be-scene crowd all year round, and this is one unforgettable, eye-catching location that offers incredible views of Boston’s skyline to boot.
  • Yvonne’s: Located in the old Locke-Ober Steakhouse, Yvonne’s is a super swanky supper club where small plates like octopus with tomatillo salsa or chicken and quinoa meatballs, plus inventive cocktails, take center stage in a dark library-like atmosphere where celebrity portrait paintings are on display. Perfect for a romantic date or fun night out with a group, you’ll want to make reservations or get here early for a table or seat at the bar.
  • Lolita Cocina & Tequila Bar: With two locations in Boston, the dungeon-chic vibe at Lolita is just as spicy as its serrano-infused tequila cocktails and top-notch street corn cauliflower tacos. I’m talking red walls, black boths, and a whole lot of wroght iron, and somehow, it still seems cozy!
  • Drink: Drink is a cocktail bar without a cocktail menu. I know it sounds weird, but trust me on this one. You simply tell the expert mixologists behind the bar what flavors you’re in the mood for, and they’ll whip you up a custom libation. Genius, huh? That being said, they do have a fixed food menu, with the likes of burgers and fried calamari.
  • The Beehive: Enjoy a side of live jazz with your dinner at this sophisticated bistro in the South End, with red hanging curtains and a bohemian, Moulin Rouge-esque vibe. The menu items range from braised lamb shoulder to dry-aged smash burger, and they also have one of the most extensive Champagne and sparkling wine lists anywhere, so get fancy!
  • Publick House: If you’re in more of a beer-and-carbs mood, order a craft brew and mac and cheese at this neighborhood watering hole with your choice of toppings, which include bacon, pulled pork, and fried egg. You’ll be able to go back out and brave the elements much warmer and fuzzier!
  • Backbar: Satisfy all of your secret speakeasy needs at Backbar, a hidden Somerville favorite with a rotating menu of creative concoctions, including a delicious milk punch. It’s small, somewhat kitchy, and has some fabulous glasswear!

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A performance of The Sl**cracker with performers on stage in Boston
For a more bawdy holiday time, check out the annual and popular Sl**cracker! (Photo Credit)

Attend a Holiday Performance 

Get into the spirit of the holiday season with your sweetie by participating in an annual tradition: taking in a performance of The Nutcracker. But luckily for you, there are two versions in Boston (ooooh, fancy). But with one big difference:

  • The Nutcracker at the Boston Ballet: Come for the annual tradition across many a US city at the Citizens Bank Opera House for The Nutcracker. Not only are the dancers and musicians spectacular, but it’s always fun to dress up, enjoy a wonderful pre-show dinner, and delight in the festive spectacle of sugar plum fairies and toy soldiers. If The Nutcracker doesn’t get you in the holiday spirit you are officially being renamed Scroge!
  • The Sl**cracker: For something completely different, slightly saucy, and brillantly bawdy, check out a beloved, cheeky holiday-themed burlesque show called The Sl**cracker in Somerville. This parody show, which debuted in Somerville 2008 and has been going strong ever since, features local dancers of the ballet AND belly varieties, along with hula hoopers, actors, and others who put a fresh and irreverent twist on the Tchaikovsky classic.

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The beginning of a Boston Bruins hockey game at the filled TD Garden in Boston
Seeing the Bruins at TD Garden is a rite of passage in Boston! Go team! Photo Credit

Root, Root, Root for the Home Teams

Boston is synonymous with pro sports, and I’d be remiss if I didn’t mention that the seasons for our basketball and hockey teams, the Celtics and the Bruins, are in full swing this time of year at the TD Garden.

The Garden is THE place for big Boston events, from games to massive concerts, so it’s a rite of passage to set foot inside — and it’s also a fantastic place to hear some wicked good local accents as spectators yell at players for better or worse.

Even if you don’t consider yourself a sports buff, the camaraderie and enthusiasm of the crowd might just have you cheering along with them. And what better way to embrace the season by coming inside from the cold to a warm drink and an ice-cold hockey rink?

Wander around a Museum

You can still get your fill of culture when it’s cold out in Boston. Fortunately, we have a number of amazing museums – many of which are included in this pass – that celebrate everything from art to history to science and provide the perfect day-long diversion when you need a break from the cold (albeit gorgeous) snow:

  • Museum of Fine Arts: A must-visit on your first trip to Boston, the stunning MFA houses an equally stunning collection that features paintings, sculptures, textiles, and photography from Africa, Asia, Europe, and the Americas. Some of the world’s most famous pieces, including John Singleton Copley’s portrait of Paul Revere, Van Gogh’s Houses at Auvers (painted right before he committed suicide), and Renoir’s Dance at Bougival, are all on display here.
  • Isabella Stewart Gardner Museum: Perhaps the most unique place to see art in the city, the Isabella Stewart Gardner Museum also has a fascinating backstory: its namesake planned and designed every aspect of the space after her husband died in 1898. Not only is the architecture — which resembles that of a Venetian palace — beautiful to behold, but so is the art within, which spans paintings, sculptures, tapestries, and more. If your name is Isabella or it’s your birthday, you can get in for free!
  • The Museum of African-American History: The MAAH has the distinction of being the largest African-American history museum in all of New England, and its complex is home to both the oldest Black church building and the oldest Black public school in the country. The Museum offers interpretive talks and tours that tell the story of the earliest advocates for justice and freedom.
  • Institute of Contemporary Art: A refreshing contrast to the myriad old stuff, the ICA is home to forward-thinking pieces of all kinds, from sculptures to video to installations made of electronics or found objects that you really just have to see to appreciate. Currently on display are Eva LeWitt’s colorful casted-and-dyed sculptures that are created from commercial and industrial materials and Deanna Lawson’s large-format photographs that capture black individuals and families in a variety of settings.
  • Museum of Science: The MOS is chock-full of cool, interactive exhibits that explain how things work on earth — like the Hall of Human Life and Engineering Design Workshop — and how things work on other planets, too; head to Cosmic Light to explore the Milky Way. Check out the world’s largest Van de Graaff generator, which creates indoor lightning, or see a movie in 3D at the IMAX theater.
  • Boston Tea Party & Ships Museum: See how all of that famous tea-tossing really went down here. This museum, which floats atop Fort Point Channel, features live historical reenactments, restored 18th-century ships, and hands-on exhibits. Considering the city’s history, this museum is a fairly new addition, as it opened its doors in 2012. And yes, in case you were wondering, you can indeed enjoy a cup of Earl Grey at the on-site tea room.

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People reading and working at tables under green lamps at the impressive Boston Public Library in Boston
Snuggling up with a good book, watching snow fall out the window, is what the Boston Public Library is good for! (Photo Credit)

Lose yourself in a good book

Snuggle up with a good book at the Boston Public Library, where the Bates Hall reading room feels like it is straight out of one of the Harry Potter movies. It begs for a spot on your Instagram feed with a barrel vault ceiling that soars 50 feet, English oak tables and chairs, and kelly green banker’s lamps.

You can even take a guided tour to learn about the history of the library and the architecture of its central buildings. Something about hiding away in a cozy library on a wintry day seems so romantic and magical, especially watching the winter snowflakes fall out the ceiling-high windows.

Visit a Brewery or Distillery

Despite a few silly remaining rules that trace back to Boston’s Puritanical roots — happy hours are still illegal here, believe it or not — Boston’s has a pretty boozy history.

Boston was actually one of the top spots for beer with the advent of the Industrial Revolution in the 1800s, and breweries have only become more ubiquitous here since then. And what better way to enjoy a frigid winter day than to double down with an ice-cold lager? If you’re into drinks of the more spirited kind, you’ll find those, too.

  • Samuel Adams Brewery: Perhaps the most famous Boston-based beer (named after one of the most famous Boston-based men), Samuel Adams HQ is located in the neighborhood of Jamaica Plain. Along with the standard tour and taproom experience, the brewery frequently hosts events with live music and specialty beers. While trying their classic Boston Lager is a must, they have a Winter Lager with a touch of holiday spice to get you in the spirit, literally.
  • Harpoon Brewery: Word on the street is that in addition to fantastic beer, the Harpoon Brewery has some of the best views of the whole city from…the…men’s bathroom? Strange but true. They even have a “Winter Warmer Holiday Cinnamon & Nutmeg Holiday Ale”, so you can have a very seasionally on-theme drink! Don’t forget to try one of the incredible pretzels here along with your pint. 
  • Bully Boy Distillers: Family-run Bully Boy has the distinction of being one of the few distilleries in Boston, churning out whiskey, gin, amaro, and other spirits. See how it’s all made, then kick back with a cocktail in the tasting room, deck out in black walls, red rugs, and yellow lamps.

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Two women window shopping at night in the snow along Newbury Street during the holiday season in Boston
Strolling down Newbury Street on a chilly winter night, popping in and out of boutique stores is one of the best ways to enjoy the season. (Photo Credit)

Shop and People-Watch on Newbury Street

Newbury Street, the ritziest shopping thoroughfare in the city, has all of the usual designer suspects and top chains, but there are plenty of cool local businesses thrown into the mix, too — plus an amazing cross-section of visitors and residents strolling past the gorgeous and well-kept 19th-century brownstones at any time of the day. And what better excuse to indulge in some retail therapy than in cold temperatures? After all, it’s very possible that you need to stock up on scarves, boots, and jackets if you weren’t quite prepared for the winter weather. 

Newbury also has a pretty fascinating backstory: it was one of Boston’s earliest roads, and began taking shape as a posh destination in the 1920s, housing boutiques and even a salon for social dance lessons. By the 1970s, when local record store chain Newbury Comics opened on the street, young people began flocking and it became just about the hippest place to hang in town and has stayed that way since.

Some other awesome places to check out are:

  • Boston Olive Oil Company: Taste samples of more than 50 different oils at this small gourmet shop. They have popular olive oils like Chilean Picual, which has a beautiful floral nose, or the Arbequina / Barnea, which has “a delicate blend of savory and herbaceous greens with notes of green apples.” These aren’t olive oils you will find in your local grocery!
  • Trident Booksellers & Cafe: One of the city’s handful of independent bookstores, Trident has been providing locals and visitors alike with a memorable combination of fantastic food and literature since 1984. Pro tip: Grab a novel to read, sidle up to the diner-style counter, and flip through it while enjoying your eggs benedit and local tea!
  • Johnny Cupcakes: Sorry, you won’t find any cupcakes here. But you will find super cool apparel at this self-proclaimed “t-shirt bakery” that sells clothes out of pastry cases. There are plenty of designs featuring your favorite characters (Pikachu, Cookie Monster, etc.) in their signature cupcake and crossbones deisgn.

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A lobster roll with fries in New England
At Neptune Oyster in Boston’s North End, you can get a mouth-watering lobster roll. I mean, doesn’t this look INCREDIBLE? (Photo Credit)

Eat your way through a Boston Food Bucket List

Sure, you can find just about every type of cuisine in Boston, but there are some dishes we do better than the rest. I’m pretty sure it’s scientifically proven. Here’s what you absolutely have to eat before you leave Boston:

  • Clam Chowder: Union Oyster House has the distinction of being not only Boston’s oldest restaurant (1826 to be exact), but it’s widely believed to have the best clam chowder in the city. A National Historic landmark, Daniel Webster was a regular customer, and you can’t go wrong with a meal here.
  • Boston Cream Pie: For this iconic treat (it’s actually the Massachusetts state dessert), you simply must go straight to the source. It originated at the Omni Parker House hotel in the 1850s after the chef and his baking staff decided to get creative and pour chocolate icing over vanilla-cream-filled sponge cake, and a legend was born. 
  • Lobster: You’re practically spoiled for options when it comes to dining on the region’s beloved crustacean, but it also depends on how you’d like to eat it. For a lobster roll, Yankee Lobster or Neptune Oyster are frequently at the top of the list. There are plenty of creative entree takes, from the lobster and waffles at Saltie Girl to the lobster pizza at Scampo.
  • Baked Beans: Those visiting Boston for the first time might be a little surprised to learn that baked beans really aren’t that big of a deal around these parts. Oh, and nobody who actually lives here — seriously, nobody — ever refers to Boston as “Beantown.” That being said, you can certainly find the classic molasses-marinated beans as a side dish on a handful of menus around the city, including those at Bostonia Public House and okay, yes, the Beantown Pub; they’re the only one who uses that name, I swear.

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Snow falling at Trinity Church in Copley Square during the winter season in Boston
If you’re lucky, your guided tour of Copley Square to Downtown Boston Freedom Trail will include some falling snow! (Photo Credit)

Take a Tour

By far, the best way to see the city is on foot. While it can be a blast to wander around on your own and stumble upon cool hidden gems, a guided tour can help give you some more context around the background of each building or home.

Since these tours last at least two hours, make sure to bundle up and wear sensible footwear for potentially slogging through some ice and snow (psst: these are my favorite winter boots – more details in this post!)

  • North End Pizza, Cannoli, and History Food Walking Tour: Education and eating in one fell swoop? It is possible! Wander around the North End, Boston’s “Little Italy,” to learn about its rich past and sample tasty treats. During this two-hour guided tour, you’ll enjoy a few slices of authentic pizza, hit up five different historic sites including the Paul Revere House, and finish things off with a cannoli. 
  • Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail: Architecture and history buffs can marvel at the stately homes and buildings in Beacon Hill and Back Bay during this two-hour walking tour that crosses into parts of the Freedom Trail. You’ll also stop by many of the spots where events that are a critical part of Boston’s history took place, like the Old State House, the Boston Massacre Site, and several churches, including the 18th-century King’s Chapel.
  • Boston Seafood Tour: When in Boston, do as the Bostonians do: eat seafood constantly. Enjoy a fully fishy day, combined with some walking and history, on this two-and-a-half hour tour that stops at some of the city’s best eateries for clam chowder and lobster rolls for both lunch and dinner, as well as bustling Faneuil Hall and Quincy Market.
  • Ghosts and Gravestones Tour: Just because it’s the “holiday season” doesn’t mean you shouldn’t get spooky. Hell, a Chirstmas Carol is literally about three ghosts! Hop on the “Trolley of the Doomed” for a 1.5-hour tour where you’ll visit nearly 400-year-old burial grounds, including the graves of John Hancock, Paul Revere, and Samuel Adams and learn about things like the biggest grave-robbing scandal in New England’s history. Merry Chirstmas, mwahahaha!

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Go Sledding

Boston is also a great destination for this classic winter activity. The only hitch is that you’ll have to bring your own sled, as unlike ice skates, there aren’t any sled rentals here.

  • Flagstaff Hill in Boston Common: Locted right next to the Frog Pond Ice Saking Rink, this small hill is the perfect place to take a leisurely sled in the middle of the winter action. You can expect lots of people on this hill, it is American’s oldest public park after all, but the winter magic is contagious and you’ll find yourself laughing along with every one else.
  • Corey Hill Park: Willing to go a bit outside of the city for an even better slope? Corey Hill Park in Brookline, which is easily accessible on the Green “C” Line (Fairbanks Street), features a 260-foot-long hill and is another fantastic spot to get some runs in. It has incredible views of the city being so high up, which also means, this hill is fast!
  • The Arnold Arboretum of Harvard University: While the Arboretum is also a little ways out of the city, it’s still accesible by the Orlange line to Forest Hills. Here among the winter wonderland of the arboretum, you can walk along snow covered trees as you make you way to Peters Hill at Walter and Bussey Streets, which has fewer trees for your (safe) sledding pleasure.

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14 Things to Do in Montreal in the Winter: The Ultimate Montreal Winter Guide

The iconic Acorn Street in Beacon Hill with brick houses with snow on a sunny winter day in Boston
Acorn Street in Beacon Hill is quintessential Boston, and in the snow it’s even better! Beacon Hill is a central and cozy place to base yourself for Boston explorations. (Photo Credit)

Where to Stay in Boston in Winter

For the quintessential Boston experience, you’ll want to stay in Beacon Hill. Between the cobblestone streets (Acorn Street is one of the quaintest — and most photographed — in the entire world), charming gas lamps, and beautiful brownstones, this neighborhood is likely the one you immediately envision when you think of Boston. It’s also within walking distance of must-visit Boston neighborhoods like Back Bay and the North End, so you’ll be right in the center of the action. 

The only downside? Most accommodations around here aren’t cheap. One of the several boutique hotels in the neighborhood will run you at least $300 per night and quite possibly much more than that. Hey, it costs to be quaint!

Fortunately, there are some great alternatives in the form of vacation rentals! Here are some of our favorites below:

  • This historic apartment on Charles Street is modern, cute, and right in the heart of Beacon Hill, with brownstones as far as the eye can see! They have multiple different options for apartment sizes as well, so it’s a great choice for couples or traveling with friends.
  • This super cute little apartment will have you snuggly and warm with it’s very own little kitchen, sitting area, and cute little bathroom. It’s the perfect place to shed those winter layers and warm up with a cup of homemade hot chocolate!
  • This sleek studio which will keep you comfortable and close to the action, with a lilttle kitchenette and full size bed. While not a huge space, it’s th perfect place to hibernate after your explorations. This VRBO does require a 7-night minimum stay, so better for a week exploration!

For a more budget option that’s still staying close to Beacon Hill, there are a couple of hostels in Theatre District / Chinatown with plenty of common space, modern design, and an overall cozy feel. They’re perfect jumping-off points for your weekend here!

  • HI Boston is located in Chinatown, near the Boston Common, Downtown Crossing, and the Boston Opera House. Not only are you near three train lines, but also within a 20 minute walk of Beacon Hill and tourist-favorite Faneuil Hall. (It isn’t included in this itinerary, but it is a cool market of food vendors, but it can be a little crowded – especially on weekends.)
  • Found Boston Common is in the Theater District, Chinatown’s neighbor. Inside a Georgian building, the period pieces harken to 19th century Boston high society – how else would you want to spend your trip?

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25 Essentials for Cold Weather Travel: Winter Travel Packing List

Brick houses in the South End at night during the holiday season during a snowstorm in Boston
Brick houses in the South End at night during the holiday season in Boston. Dress for the cold so you can enjoy beautiful winter evenings like this! Photo Credit

What to Pack for Boston in the Winter

Boston is all about comfort over style any time of the year, and that is especially true in the winter. You’ll definitely want to bring lots and lots and LOTS of layers, plus hats, scarves, earmuffs, and well-insulated boots for trudging around in the potential snow. The warmer you are, the more fun you’ll have — I promise! Mainly because you won’t be focused on how you’re freezing your butt off.

Ever heard that saying, “there’s no such thing as bad weather, just bad clothing?”  In addition to keeping you warm as you explore, weatherproof clothing is especially important if you’re going to do outdoor activities. So, be sure to bundle up in your favorite cozy sweaters, a warm coat, and waterproof winter boots! We’ve got all the details you need.

We recommend wearing a base layer underneath your clothing on cold days during your winter trip – that means that the layer closest to your skin should all be made from merino wool. Merino wool is super warm, incredibly soft (nope, it’s not itchy) and much more lightweight than synthetic fabrics, as well as being naturally antibacterial, which means you can re-wear it without the re-wear funk. If wool isn’t your thing, wear an equally insulating textile like hemp or silk. Avoid non-insulating fabrics like cotton, and remember that natural fibers are pretty much always better than manmade textiles like polyester.

After your base layer, you’ll need to add on at least 1 additional layer before your outerwear, like a pair of pants and a sweater. On REALLY cold days, where the temperatures are below 10 degrees, we recommend adding on another base layer before your clothing layer & outerwear. And if you’re doing winter activities, add a waterproof layer as well, like lined snow pants. For more winter travel packing tips, head over to our Cold Weather Packing Guide.

Here are our tried and true travel essentials for winter travel.

  • Merino Wool Base Layer Leggings: These super comfy 100% wool leggings function just like long underwear. They’re made of soft, super-luxurious wool and make your legs feel like they’re being hugged by an extremely soft sheep. Jeremy has this pair. You’ll want to wear these underneath your pants on cold days during your trip.
  • Merino Wool Base Layer Undershirt: Laying is crucial when it’s this cold, and you’ll need to start with a layer of insulation on top and bottom. If it’s not terribly cold that day, I can sometimes get away with a short sleeved or even sleeveless wool base layer. I also defintey just wear my long sleeved base layer as a shirt somtimes! This is mine and this is Jeremy’s.
  • Wool Socks: Make sure you don’t just have run-of-the-mill acrylic socks for your trip – they won’t keep your feet warm while you’re out in the snow! Instead, bring socks that are primarily made of soft, heat-regulating wool, like these or these.
  • Warm Walking Boots: We recommend boots that can withstand ice or snow, are weatherproof and waterproof, and are comfortable enough to walk in for HOURS. Sounds darn near impossible, right? Well, it’s not. We’ve found the best boots for winter, and we’re OBSESSED with them (and yes, we both have the same ones. Because we’re kinda gross like that). They’re cute, they’re insanely comfortable, they’re waterproof leather with warm thermal insoles, and they’re extremely lightweight and foldable so you can stuff them in your bag when you travel. We can’t recommend these boots enough, and they’re the only shoes we bring on cold weather trips. They’re made to last and they’re worth every cent. Here are my boots and Jeremy’s boots. You can read more about them in our round-up of our favorite travel shoes for women or for men.
  • Travel Jeans:  My favorite travel jeans have 6 POCKETS. 6!! And 2 of them are zipped and hidden inside other pockets, for extra pickpocket protection. They’re super stretchy and buttery soft, dry quickly even after walking through the snow, and roomy enough to layer over an insulating base layer (or two). They’re cozy enough to wear on a plane, stretchy enough to accommodate that 5 extra pounds of holiday weight I always seem to bring back home with me, and they’re super cute! We’re both obsessed. You can get a pair of men’s or women’s jeans on the Aviator USA website.
  • Warm Flannel Shirt: I’m in LOVE with the MerinoLux flannel button-down from Royal Robbins. It’s stretchy, it’s cozy, it’s blended with merino wool (yassss) and most importantly, it’s warm AF and super breathable. It’s also wrinkle-resistant, odor-resistant, and moisture-wicking, and has a hidden zip pocket – so basically everything you could ever ask for in a flannel shirt. I’ve been searching for the perfect flannel for YEARS (you know, like one that didn’t give me that annoying button-down boob gap and allowed me to actually cross my arms) and this is The One. I love it! Here’s mine and Jeremy’s.
Lia frolicking in the snow in Banff in the winter.
It’s important to dress appropriately for snow frolicking, so that you can frolic freely without worrying about, like, how much snow you’re going to get down your shirt (yikes). Practice safe frolicking, y’all!
  • Lined Leggings: On very cold days, I add an extra layer of insulating warmth by throwing a pair of lined leggings on over my base layer and under my jeans (I’ve also worn them without extra pants on top of my base layer because leggings are real pants, fight me). I have two pairs of warm lined winter leggings, one lined with merino wool and one lined with fleece.
  • Warm Hat: A warm hat is an absolute necessity. It also doubles as a super cute accessory! Did I just rhyme? You want a hat that will stay on your head when it’s windy wind and keep your ears nice and warm – bonus points if it’s lined. Personally I’m a fan of the ones with poofs on top, like this or this. Jeremy is more of a purist, and likes to wear beanies like this one, which is made from earth-friendly recycled wool and nylon.
  • Warm Coat: Your jacket is arguably the most important thing you’ll bring on a winter trip other than your shoes. It has a big job – namely, keeping you warm but not sweaty, allowing you to actually move your arms, and letting you explore for hours without feeling heavy or restrictive. Plus, it’s gonna be in almost all of your photos.  I bring this this cozy fleece-lined coat with me, and Jeremy wears a wool-blend coat similar to this one and this one.
  • Packable Down Jacket: Jeremy and I each bring two jackets each on our winter trips: our heavy/bulky coats, and a lightweight, travel-friendly packable down jacket. It’s perfect for those days when I want the freedom of not wearing a big heavy coat, and it’s also a fantastic added layer of warmth on super cold days. For this trip, I brought this down jacket and Jeremy brought this down jacket.
  • Gloves: Don’t go outside in the winter without gloves on! Jeremy and I both have these wool gloves that work with touchscreens, because let’s face it, I have a hard enough time using my phone without wearing gloves. Over those gloves we layer on a thicker pair that allows us to do things like throw snowballs at each other.
  • Scarves:  I LOVE a chunky scarf. They’re my favorite accessory! I love this super soft scarf from Royal Robbins, which is blended with wool and turns into a cute shawl or infinity scarf with a few well-placed buttons. I’m also a big fan of scarves that are big enough to double as blankets, like this one or this one.
  • Winter Sports Gear: If you’re planning to go skiing or snowboarding on your trip, bringing a few things can easily be packed in your suitcase will save you cash on rentals. We recommend these goggles and these gloves for snowboarding, and these travel-friendly crampons for snowshoeing.  

Whew! That should keep you warm and toasty. Oh hey, want a printable version? Just sign up below and we’ll send a checklist straight to your inbox.

Printable Winter Packing List

This FREE 3-page printable packing list will help make sure you don’t forget anything for your next winter trip. We’ll also send you our favorite travel tips!

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25 Essentials for Cold Weather Travel: Winter Travel Packing List

About Our Contributing Writer: Kim Windyka is a Boston-based writer and coauthor of the guidebook 111 Places in Boston That You Must Not Miss. Her work has been published by The Atlantic, McSweeney’s Internet Tendency, New York Magazine, Fodor’s, xoJane, HelloGiggles, The Outline, and the New Hampshire Visitors Guide, and her essays have appeared in the books Madonna & Me and Popular: The Ups and Downs of Online Dating from the Most Popular Girl in New York City. A copywriter by day, she has more than a decade of experience across industries including travel, tech, finance, and fashion. You can see more of her work at www.kimwindyka.com, follow her on Instagram at kimmyloowho, and on Twitter at @kimlw.


Which one of these things to do in Boston in winter are you most excited to try first? Comment below and let us know!

Psst: Inspired for more wintery trips? …. Here are some of our favorite winter posts!

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Our Top Travel Tips & Resources

Here are our favorite travel tips & resources for saving money and planning travel logistics! For more tips, check out our travel tips resource page or our guide to planning a trip.

  • Booking Flights: To score flight deals, search on Google Flights or Kayak. Money-saving tips: fly mid-week or on the weekend; fly carry-on only on a budget airline; and take red-eyes or early morning flights.
  • Accommodations: We usually stay in budget-friendly vacation rentals, boutique hotels or private rooms in hostels. We use Booking.com to book hotels (we love their flexible cancellation policy) and Hostelworld to book hostels (low deposit, easy change/cancellation, and excellent reviews). For vacation rentals, we prefer to book using VRBO because they’ve got lower fees and better support than Airbnb, and we’re not fans of Airbnb’s unethical track record. You can also book vacation rentals on Expedia and Hotels.com. We also use TrustedHousesitters as both hosts (for our home and our fur-child) and travelers!
  • Travel Insurance: We always, always, ALWAYS buy travel insurance for international trips, and we STRONGLY suggest it – visit our Travel Insurance Guide to find out why. We recommend either World Nomads or SafetyWing for international travel insurance. SafetyWing is one of the few policies that covers Covid-19, and they have excellent monthly policies that are perfect for Digital Nomads and long term travelers!
  • Travel Credit Card: We book all of our trips on our favorite travel credit card. Not only do we earn cash back that we can spend on more travel, but the card offers fantastic travel perks like travel insurance, trip delay and cancellation coverage, lost baggage reimbursement, and rental car coverage, which helps protect us on our travels. Learn more here.
  • Vaccines & Meds: We use the travel guides on the CDC website to research recommended medications and vaccines for international trips. We always recommend getting every vaccine recommended by the CDC! You can get them at your primary care doctor’s office or a walk-in pharmacy.
  • Tours: We love booking guided tours, especially food tours and walking tours, to get a local’s perspective and a history lesson while sight-seeing! We book our tours using Viator and GetYourGuide.
  • Transportation: We use Rome2Rio to figure out how to get from place to place using public transit, and book local transportation online using Bookaway wherever we can. When we book a rental car, we use Kayak to compare rental companies and find the best deal.
  • Luggage Storage: Whenever we’re checking out early or taking advantage of a long layover, we use LuggageHero to safely store our luggage while we’re running around. Use the code PRACTICALW for 2 hours of free luggage storage on us.
  • What to Pack: Here are the travel essentials that we bring on every trip. We also have packing lists for hot weather, cold weather, and many more. Take a look at all of our packing guides!



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