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Boston in Winter: The Ultimate Guide 

Boston in Winter - George Washington Statue in Boston Public Garden with snow all around and blue sky

I visited Boston many years ago, just for a day trip, so following the success of the guest post about Free Things to do in Boston, I asked Tegan and Alex from Why Not Walk to share their top tips for visiting Boston in Winter and they certainly came through!  Check out their ultimate guide to visiting Boston in winter:  

Boston is the capital of Massachusetts and is one of the oldest municipalities in the United States.  Famous for its history, whale watching tours and delicious food, Boston is a wonderful city to visit at any time of year, but here is why you should visit Boston in winter.

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Why Visit Boston in Winter?

Many dismiss Boston as too cold in the winter for a visit, picturing howling winds and icy roads. However, given that Boston is a coastal city, its proximity to the Atlantic Ocean truly gives it the best of both worlds: it’s much more temperate than the rest of the state and region in the wintertime, but still gets to enjoy several gorgeous, fluffy snowfalls each year. Boston is bursting with fun things to do all year, but we would argue the wintertime is an extra special time to visit.

Stroll along romantic cobblestone streets, stop for a hot chocolate or perhaps some outdoor ice skating, and enjoy Boston’s wealth of museums, local breweries, charming neighborhoods, sports teams, and more. Read on for all our best tips for the ultimate winter visit to Boston, and for more Boston tips for any time of year, check out Why Not Walk’s Boston-area landing page here.

Boston Common - Things to do in Boston in Winter
Boston Common – Things to do in Boston in Winter

What to Wear in Winter in Boston

Layers, layers, layers! We cannot stress this enough. While Boston’s temperatures aren’t quite as cold as people like to think they are, what we do have in spades here is wind. The downtown and Seaport areas in particular are known for wind tunnels that can get fairly brutal due to their tall buildings, so we definitely recommend a scarf and gloves, as well as a jacket with a hood or a beanie or hat.

As Boston is a walking-heavy city, you should definitely bring warm and comfortable shoes, preferably waterproof ones. We especially recommend boots (like Uggs or Timberlands) and of course some nice, thick socks. 

As for a coat, down or alternative down is the way to go. You’ll see many Bostonians rocking the knee- or ankle-length coats. This isn’t totally necessary if you usually live in warmer climes, but definitely make sure to bundle up, and plan a mix of indoor and outdoor excursions for each day. 

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Things to Do in Boston in the Winter

You could live in Boston for years (like we have) and still not experience everything Boston has to offer. Boston has something for everyone, from the history aficionado to the sports fanatic to the autumnal leaf-peeper.

While visitors flock to Boston and the region in the fall to see autumn foliage, we’d argue that a beautiful snowfall gives the leaves a run for their money. If a winter “city break” is what you’re after, Boston will not disappoint. Keep reading for all the best tips on the best things to do in Boston in winter, the city’s top winter attractions, and a sample Boston 2 day itinerary. 

Charles River in Boston
Charles River in Boston

Visit the Museums in Boston

When the weather is poor, getting inside and visiting some of Boston’s incredible museums is a great way to keep warm and dry.

The Museum of Fine Arts (Back Bay/Fenway) houses over 450,000 works of art at the world’s 17th-largest museum. 

The Isabella Stuart Gardner (near the MFA): Once the home of notable Bostonian Isabella Stuart Gardner, the house and artwork were turned into a museum under the terms of her will. The ISG gained notoriety for a 1990 art heist that remains unsolved to this day. Don’t miss the gorgeous courtyard in the center.

The Boston Science Museum (Lechmere): though a bit dated, science fans will enjoy the Science Museum’s many exhibits and indoor zoo.

The Museum of African American History (Downtown): Don’t miss a visit to New England’s largest museum dedicated to preserving and honoring African-American history, located in the African Meeting House– the oldest Black church building in the U.S.

The Institute of Contemporary Art (Seaport): If modern and contemporary art is more your scene, the ICA does not disappoint. It also has lovely views of the Harbor area, and its neat architecture is an exhibit unto itself.

Seaport - Attractions in Boston to Visit All Year Round
Seaport – Attractions in Boston to Visit All Year Round

Check Out Vintage Movies, Glamorous Shows and Improv Comedy

These are some of our favorite places for a more unique Boston experience, especially during the winter!

Watch vintage movies (often in 35mm!) at Brattle Theatre (Harvard Square) or the Coolidge Corner Theatre (Brookline.) Coolidge Corner is the oldest Art Deco theatre in the area, built in 1933.

Get dressed up for a show at the Boch Center’s Wang or Shubert Theatres or the Emerson Colonial Theatre. You will be awe-struck at the beautiful decor, sweeping ceilings, and enormous chandeliers. All 3 of these theatres opened in the early 1900s and are some of the oldest continuously operating theatres in the region. You can also enjoy Boston’s premier symphonic ensembles at the Boston Symphony Orchestra (Fenway.)

Alternatively, laugh ‘til your sides hurt at a comedy show at ImprovAsylum (North End.)   

Warm Up with Hot Chocolate

Any excuse for a tasty hot chocolate is fine by me, and these tasty treats will warm you right up on a cold Boston winter day!

The Mexican hot chocolate at Ogawa Coffee House is absolutely decadent, and its location in downtown Boston is perfect if you’ve just gone ice skating at the Frog Pond (more info on that below!)

Located in the swanky Back Bay, LA Burdick offers all sorts of artisanal chocolate offerings, including hot chocolate.

If you don’t want to choose just one, check out seasonal Hot Chocolate Flights at The Met Back Bay. You can even ask for yours to be spiked!

Bonus: If hot chocolate isn’t for you, and you’re more in the mood for normal chocolate, check out the Chocolate Factory Tour at Taza in Somerville.

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Ice Skating and Winter Sports in Boston

The ultimate Boston winter experience is outdoor ice skating at the Boston Common Frog Pond. The Common is the “Central Park of Boston,” and located in the heart of downtown. Tip: if you go after sundown, there are twinkly lights all over the park that really set the scene! There is also seasonal ice skating at City Hall Plaza’s Boston Winter installation, as well.

If indoor ice skating is more your scene, check out the Steriti Ice Rink in the North End. Admission is free, and you can rent skates for a few dollars. Pair this with a visit to the North End (Boston’s Italian neighborhood) and Boston Harbor afterwards. 

If you don’t want to splurge on (very pricey) hockey tickets, you can watch the Boston Bruins practice at Warrior Ice Arena. 

Enjoy the Red Sox stadium tour without the crowds– it’s available year-round!

If you are interested in attending sporting event while you are in town, check out the TD Garden calendar for Bruins and Celtics tickets, as well as concerts! 

Fenway - The Home of the Boston Red Sox
Fenway – The Home of the Boston Red Sox

Brewery + Distillery Tours

What better way to warm up on a wintery day in Boston than with a tasting of your favorite tipple?

Sam Adams (Jamaica Plain): Sam Adams is definitely touristy, but worth a visit if you’re visiting Boston for the first time, or if you’re interested in how one of the nation’s largest breweries operates. The tour is free (make sure to reserve ahead of time), and you get samples and a free small glass with your tour. Sam Adams recently opened a new taproom in the Faneuil Hall area as well. 

Harpoon Beer Hall (Seaport): Harpoon wins “best brewery tour” in our book, hands down. Harpoon is a super fun atmosphere– they’re employee-owned, make amazing pretzels with their leftover beer byproduct, and their beer hall in the Seaport can’t be beat. Definitely sign up for their brewery tour– it costs $5, but includes some time at the end for unlimited samples! 

Boston Harbor Distillery (Dorchester): Their table-side tasting tour offers several samples and a history of their operation for $10/pp. They also have a VIP tour ($40/pp), offering a “back-room of whiskey-making” experience. Also in Dorchester is Bully Boy Distillers, which also offers tours and tastings for $10 as well. 

Explore Beautiful Wintry Neighborhoods in Boston

There are some lovely neighborhoods in Boston where you can talk a stroll, no matter what the weather.  Just wrap up warm and enjoy!

Beacon Hill

Located right behind the Boston Common with Charles Street as its main drag, don’t miss a visit to Beacon Hill while in Boston. Characterized by its cobblestones and mix of Victorian- and Federal-style brick row houses and antique black streetlamps, Beacon Hill is so charming and picturesque – and quintessentially Boston. Don’t miss the State House with its gold dome, especially beautiful when covered in snow, and Acorn Street, one of the U.S.’s most-photographed streets.  

Winter in Boston - a Snowy State House in Boston
Winter in Boston – a Snowy State House in Boston

Back Bay

Likely Boston’s most “fancy” neighborhood, Back Bay is also home to beautiful architecture, as well as a large shopping district including Newbury Street and the sparkly Prudential Center. The Commonwealth Avenue Mall, leading up the Public Garden, is beautiful in any season.

North End

Boston’s Italian district is also Boston’s first neighborhood, continuously inhabited since 1640. The North End is adorned with narrow, winding streets and some of Boston’s oldest surviving architecture. Don’t miss American Revolution hero Paul Revere’s house and the infamous Old North Church (of “one if by land, two if by sea notoriety), both on the Freedom Trail.

North End Columbus Park - Places to visit in Boston in Winter
North End Columbus Park – Places to visit in Boston in Winter

Places to Check out Snow in Boston

If snow is what you’re after, you have a good chance of seeing it between December and March, with January and February usually clocking in as the coldest and greyest months with the most chance for that sort of precipitation. There is sometimes snowfall as late as April, to the delight of visitors and chagrin of locals.

Top Tip: If you want to increase your chances of seeing snow, plan a quick day trip to Western Massachusetts and the Berkshires while you’re in Boston, as they have fairly constant snow cover and are only about 2 hours away.

Closer by, the towns surrounding Boston are excellent places to enjoy a fresh snowfall – Brookline and Chestnut Hill, in particular, have beautiful Victorian architecture and stately homes that make a gorgeous backdrop for photos, and their wonderful reservoirs and parks are at their most impressive when covered in snow. 

Chestnut Hill - Snow in Boston
Chestnut Hill – Snow in Boston

Holidays in Boston

Boston really gets into the swing of the holiday spirit during the winter, check out the variety of holiday-themed pop-ups at bars around the city, including the Tiki bar Christmas pop-up at Shore Leave (South End), Pop-up igloos at the Envoy Hotel (Seaport) and a Hanukkah-themed pop-up at Backbar (Somerville).  You can even get your fix of Holiday movie-themed cocktails at Precinct Kitchen & Bar (Back Bay)!

Christmas in Boston

Holiday and Christmas lights appear all around the city during the winter.  The Boston Common is festooned with twinkling lights, as well as a lighting ceremony for a huge Christmas tree. Visit Faneuil Hall downtown, to see Quincy Market decorated with lights and decorations, and book tickets to see the Nutcracker ballet at the Boston Opera House.  

Christmas in Boston - Holiday Decorations in Market Square
Christmas in Boston – Holiday Decorations in Market Square

How to Spend Winter in Boston 2 Day Itinerary

Boston in Winter Itinerary Day 1

Start your day in Copley Square, visiting its churches and the Boston Public Library, and exploring the Back Bay neighborhood. Tip: the BPL is one of Boston’s best-kept secrets. Built in 1888, its interior is absolutely gorgeous. Don’t miss the 2nd floor Bates Room for old-school study vibes, or the outdoor courtyard in the middle (follow the signs on the ground floor.)

Meander along Newbury Street, perhaps stopping in one of its chic eateries for brunch as you walk along. Newbury Street also has Boston’s most upscale shopping, if that’s in your budget. Pop over a block to the Commonwealth Avenue Mall promenade for a snowy stroll.

Continue down to the Prudential Center, a shiny shopping center where you can thaw for a little bit on a chilly day. For a lovely Italian market experience, check out Eataly. 

If you’re in the mood for some seafood for lunch, check out Saltie Girl. If that’s a bit out of your budget, enjoy locally-sourced DIY bowls at Dig Inn.

Boston Public Library
Boston Public Library

In the afternoon, take the green line or a ride-share a few stops to the Fenway area to visit the Fenway Baseball Stadium, the Museum of Fine Arts, and the Isabella Stuart Gardner Museum. If you’re not feeling too cold, the Fens area of the interconnected parks known as the Emerald Necklace is lovely in the winter.

In the evening, check out the South End for trendy eateries and bars. Stop into the Beehive for a drink and live jazz music, or Barcelona Wine Bar. If you decide to stay in the Copley area, Lolita is another favorite, for frozen margaritas and other cocktails in what we like to call a “dungeon-glamour” locale.

Lastly, a favorite bar in Seaport is Drink, for really neat DIY cocktails. Here’s how it works: you sit down at the bar, tell the bartender what combination of flavors and liquors you like (e.g. vodka and citrus, or “drinks that don’t taste like alcohol,” or rum and bitter), and they make you a surprise. It could be a bartender invention or an obscure combination – you never know!

Boston in Winter Itinerary Day 2

In the morning, take the MBTA’s green line or a ride-share to the Boston Common to start the Freedom Trail: a 2.5 mile walking tour of Boston’s esteemed role in the history of the United States. Pair the Freedom Trail with its sister tour in Beacon Hill, the Black Heritage Trail.

For a full, step-by-step guide to both trails (plus bonus local content!), check out Why Not Walk’s definitive guide to the Freedom Trail. We recommend allotting at least a half day for the Freedom Trail. While it can theoretically be done in about 1.5 hours, you will definitely want to spend longer at various sites!

The Freedom Trail ends in Charlestown, at the Bunker Hill Monument and the USS Constitution. You can spend some time exploring the area, or make your way back downtown for lunch.

For quick bites downtown, check out Sam LaGrassa’s for sandwiches, Dig Inn for locally-sourced bowls (if you didn’t go to the Back Bay location yesterday!), or Clover Food Lab for vegetarian-friendly fare. In nearby Chinatown, there are delicious dim sum and dumpling restaurants galore. One particular favorite is Gourmet Dumpling House.

Faneuil Hall Boston
Faneuil Hall Boston

Alternatively, there is something for everyone at Faneuil Hall Marketplace, which is a stop along the Freedom Trail if you’d like to take a break then. Here, you can sample Boston’s famous lobster rolls (we recommend hot rolls more than cold!) drizzled with fresh butter or clam chowder in a bread bowl. Note: For a less-touristy place to try lobster rolls, there’s always Yankee Lobster in Seaport.

In the afternoon, tour the North End, Boston’s quintessential Italian neighborhood. We hope you saved some room from lunch, because you can’t miss sampling hand-made Italian cookies, cannoli, gelato, and other treats here. Don’t miss the epic Mike’s Pastry versus Modern Pastry cannoli battle, at the very least.

You can stay in the North End for dinner too, choosing one of many restaurants (you can’t go wrong!) such as Regina’s for pizza, or Trattoria Monica, Giacomo’s, or Antico Forno for pasta and other Italian fare. Note that Giacomo’s does not take reservations, so you will likely have to start lining up at around 3PM or earlier to get in for dinner. This may not be worth it if you’re on a tight schedule.

In the evening, enjoy the downtown Boston bar scene at classy Yvonne’s or the Marliave, or the really fun dive bar Biddy Early’s. Watch live Irish music with the Guinness on tap flowing at Black Rose. If breweries are more your scene, check out Harpoon or Trillium in the Seaport, Brato in Allston-Brighton, Dorchester Brewing Company in Dorchester, or Lamplighter in Cambridge.

We hope you enjoyed this locals’ guest post to Boston. Feel free to reach out anytime if you have any questions or want more tips.

About the Authors

Tegan George & Alex McKenzie

Tegan and Alex are travel, hiking, and biking enthusiasts currently based in Boston, USA. There is nothing they love more than exploring new places by walking, and they have visited over 30 countries together since they met in 2015. Their love for “walking the world” led them to found Why Not Walk, a travel guides site. Follow them on Instagram, Facebook, or Pinterest to start planning your next adventure.

If you’re looking for travel insurance for your trip to Boston, get a quote now from World Nomads.

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Last updated: October 11, 2020

One thought on “Boston in Winter: The Ultimate Guide 

  1. Ryan K Biddulph says:

    Nice post Tegan and Alex. Super comprehensive guide here. Well done. I am heading to Middleton in under 2 weeks for a month long trip, about. We will miss Boston during winter but may take a trip into town as we will be about 30 minutes outside of Beantown.

    Ryan

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