Boston in Winter: The Ultimate Guide 

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 to make the most of the special winter activities and events.

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Winter Weather in Boston

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.

That said, average winter temperatures in Boston hover around or just below freezing, with January typically being the coldest month.  January also usually gets the most snow, although you can expect some snow from November through to April.

Why Visit Boston in Winter?

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.

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. 

Recreate the Boston Tea Party

Yes, it’s probably the most touristy thing to do in Boston, but if it’s your first time in the city then learning about the famous Tea Party at the interactive museum is a fun way to forget the weather!  This ships and museum tour runs several times a week even in the winter and allows you to travel back in time to 1773 to be part of the famous Boston Tea Party and the events leading up to the American Revolution.

You can explore fully restored replicas of the Tea Party ships, take part in an interactive museum tour and re-live the events of the day with live actors and 3D holograms.  You’ll even have the chance to throw your own tea overboard! 

Money Saving Tip

If you’re planning to visit several museums, you may save money with the Boston Go City All-Inclusive Pass which includes free entrance to more than 40 attractions including a trolley tour, the New England Aquarium, the Museum of Science, a Fenway Park Tour and more.  See what is included and compare it to where you want to go to make sure it is worth it for you.

Visit the Museums in Boston

Wondering what to do in Boston when it snows?  When the weather is poor, getting inside and visiting some of Boston’s incredible museums is a great way to keep warm and dry and learn something at the same time!

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

The Isabella Stewart 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.

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 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!

If you like to combine your cocoa with Christmas carols, this cruise on Boston Harbor takes in the beautiful sights of the Boston Skyline while listening to Christmas music and carols as you sip on your cocoa. 

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 is 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! 

Brewery + Distillery Tours

What better way to warm up on a wintery day in Boston than with a tasting of your favorite tipple?  You could join a tour that takes in three of the top breweries in town, or check out our recommendations below:

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 $20/pp. They also have a VIP tour ($50/pp), offering a “back-room of whiskey-making” experience. Also in Dorchester is Bully Boy Distillers, which is worth a look too.

You should also check out these beer and brewery tours that are guaranteed to keep you warm and tipsy!

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.  

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 to 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.

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. 

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.  

New Year’s Eve in Boston

First Night Boston is the city’s biggest New Year’s Eve celebration.  It is family-friendly and alcohol-free so if you are visiting Boston with kids then they will love it!  There are fireworks over Boston Common at 7pm, and another spectacular display over Boston Harbor at midnight. 

You can watch a parade, admire ice sculptures, watch a pyrotechnic show and catch some live music performances.  It is one of the best things to do in Boston in December, and a wonderful way to welcome in the New Year.  This website has more details about the events.

Want More Winter Travel Ideas?

Check out these blog posts for your winter vacation inspiration!

 

• Chicago in Winter
• Boston in Winter
• Denver in Winter
• Colorado Springs in Winter
• Phoenix in Winter
• Boise Idaho in Winter
• Orlando in Winter

 

• Salt Lake City in Winter
• Seattle in Winter
• National Parks in Winter
• Niagara Falls in Winter
• Toronto in Winter
• Banff in Winter
• Lake Louise in Winter

How to Spend Winter in Boston 2 Day Itinerary

If you need some more tips for things to do in Boston during the winter, this Boston itinerary has more suggestions for you! 

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.

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.

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, Dorchester Brewing Company in Dorchester, or Lamplighter in Cambridge.

Where to Stay in Boston This Winter

After a long day of exploring Boston, Massachusetts, you’re going to need somewhere to rest your head and get energized for the next day.

Here are a few great options for hostels and hotels in Boston for your visit:

HI Boston Hostel: This modern, environmentally friendly hostel is near Boston Common, Chinatown, the subway and most of the city’s sights. Dorms feature individual lockers and personal shelves, reading lights, and power outlets. You’ll get lots of privacy balanced with common spaces for socializing when you stay here. >>>CHECK PRICES

The Verb Hotel: A small, music-themed boutique hotel near historic Fenway Park. Fans of rock ‘n roll will love the funky decor and party atmosphere. Plus, it’s literal steps from some of Boston’s best restaurants, shopping, and activities. >>>CHECK PRICES

The Godfrey Hotel Boston: Stylish, sophisticated, and centrally located, this hotel provides excellent access to just about everything a guest would want to do in Boston.  >>>CHECK PRICES

If you’d like more options, you can browse all hostels in Boston on Hostelworld, or find great value hotels on Booking. There are also various options for Airbnbs in Boston too, take a look at some of the rental homes available here.

BROWSE HOTELS IN BOSTON

Travel Tips for Boston

We hope this post has inspired you to book your winter vacation in Boston this year!  Be sure to check out these extra travel tips to help you plan the best trip to Boston you can:

Getting There

• Use Skyscanner to find cheap flights to your destination.
• Public buses are the cheapest ways to get to your accommodation from the airport, but a shared shuttle transfer is quicker and cheaper than a taxi - you can pre-book those on GetYourGuide or Viator
• Try Omio for booking trains and Busbud for buses including Greyhound and Flixbus.

Where to Stay

• For hotels, I use Booking.com to check reviews and find the best deals on hotels and apartments wherever I'm travelling to.  Hotels.com is another good site.
• If you're on a tight budget, use Hostelworld to find the best hostels all over the world

Hire a Car

• Get a quote for car hire with Discover Cars who compare car rental deals from many companies so that you can choose which is best for your trip.

Book Tours and Activities

• I use GetYourGuide or Viator to book everything from skip-the-line entry tickets to food tours as I can compare options from several companies and choose the best one for me
• If you're staying in a hostel, check out their tours and activities which are usually free or very cheap - and a great way to meet people!  

Get Travel Insurance

• Unfortunately, things can and do go wrong when you travel.  I never leave home without travel insurance, so consider getting insurance for your trip to cover things like adventure sports and activities as well as emergency medical, lost luggage, stolen items, trip cancellation and more.  
• Get a quote for your trip from True Traveller if you're based in the UK, or World Nomads or SafetyWing which both offer travel insurance for backpackers and long-term travellers.  Alternatively, use a comparison site like Travel Insurance Master to find the best cover for you.

Check Your Travel Documents

• Don't forget to check the validity of your passport and any other documents for your trip.  Use iVisa to check if you need a visa to visit your destination, and get up to date official travel advice from your government, for example on the Department of State website in the US or the UK government website.

Get Cheap Currency

• When travelling abroad, using a travel bank account like Wise means you get great deals on foreign currency - including a fee-free transfer of up to £500 when you use this link to sign up. 

Top Money Saving Tip for Backpackers

• Work exchanges are a great way to travel for longer and extend your trip as you can save a ton of money on accommodation.  Get an extra $10 discount on Worldpackers here or learn more about work exchanges.

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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Just to let you know, this post may contain paid or affiliate links, which help to maintain Tales of a Backpacker and give me the chance to keep travelling, and to keep creating awesome content for you!  I only recommend goods and services I believe are useful and reliable.