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22+ Best Things To Do In Boston In The Winter From A Local

Boston in winter is a magical experience. The city comes alive with holiday decorations, seasonal events, and plenty of indoor and outdoor activities. Whether you’re a local or a visitor, you’ll find no shortage of ways to embrace the chilly weather.

Today I’m sharing everything you need to know about visiting Boston in the winter from a local perspective, as well as 22+ best things to do in Boston during the winter season!

Why Visit Boston In Winter?

The best things to do in Boston in winter

Visiting Boston in the winter is an experience. And while Boston is beautiful during all four seasons, there are plenty of reasons to go in the winter specifically.

One of the best things about visiting Boston in winter is that you’ll encounter fewer tourists. This means shorter lines at popular attractions and a generally less crowded experience as you explore the city. Boston can get pretty packed in the summer, making it hard to actually experience history.

Plus, winter is generally considered the low season for tourism in Boston, so you’re more likely to find better deals on flights and accommodations. Many attractions also offer off-season pricing. The price differences can be huge.

Boston in winter is not short on things to do. From ice skating at Frog Pond to holiday markets and seasonal concerts, the city offers a host of winter-specific activities that you won’t find during other times of the year. Because we’re used to winter up here, we have tons of activities that you can only do during the winter. Hey, we need to get through the cold months somehow. And Boston has a rich array of indoor activities, from museums to historic sites and theaters. Winter is a great time to explore these options without feeling like you’re missing out on outdoor activities.

If you come during the holiday season, Boston is something to behold. With tree lighting ceremonies, holiday markets, and decorations all around, the city becomes a winter wonderland. If you love the holidays, Boston in winter is a perfect fit.

And if you’re a fan of winter sports like skiing, snowboarding, or sledding, there are several places within a short drive from Boston where you can hit the slopes or find a good hill for some classic winter fun. I love how close Boston is to all New England winter sports because you can experience the winter city magic and do the rural New England thing all in one trip.

Lastly, Boston is a walkable city, and its public transportation system is efficient. Even in winter, the city is easy to get around, whether by foot or by using the T (subway). One of the perks of being a smaller city is that it’s not hard to get somewhere, even during chilly winter days.

Best Things To Do In Boston In The Winter:

Here are some of my favorite Boston winter activities that you’ll definitely want to schedule in.

22. Ice Skating

The best things to do in Boston in winter

Ice skating is one of those activities that epitomizes Boston in winter. Whether you’re a local looking for a seasonal activity or a visitor wanting to embrace the winter chill, strapping on a pair of skates is an ideal way to do it. Here’s the scoop on ice skating in Boston, including some top spots to check out.

Frog Pond:

No discussion about ice skating in Boston would be complete without mentioning Frog Pond. Situated in Boston Common, the city’s historic park, Frog Pond is transformed into an outdoor skating rink every winter. It’s perfect for skaters of all ages and skill levels. Rentals are available, and there’s a café where you can grab some hot cocoa or a snack.

This is my #1 recommended area to ice skate in Boston. Everyone should go to Frog Pond once!

Frog Pond generally opens for the winter season from late November or early December through March, weather permitting. The rink has specific hours for public skating, which can vary depending on the day of the week and whether there are any special events or private bookings.


Kendall Square Community Ice Skating:

Located in Cambridge, not too far from downtown Boston, the Kendall Square rink offers another outdoor skating experience. This rink is less crowded than Frog Pond, making it a good option if you’re looking for a more relaxed environment. They also offer skate rentals and lessons if you’re a beginner.

Steriti Memorial Rink:

Located in Boston’s North End, the Steriti Memorial Rink is an indoor option that offers free public skating. It’s particularly popular among locals and offers a view of the Boston Harbor. It’s a good alternative if you’re looking for a place to skate without braving the outdoor chill.

Warrior Ice Arena:

If you’re a hockey fan, you might want to check out Warrior Ice Arena, the practice facility for the Boston Bruins. The arena is open to the public for skating at certain times and offers a high-quality ice surface. It’s located in the Boston Landing area, which has restaurants and shops to explore before or after your skate.

21. Visit Faneuil Hall Marketplace

The best things to do in Boston in winter

Faneuil Hall Marketplace is one of the prime spots to visit in Boston in winter. The historic area is transformed with twinkling lights and holiday decorations. Street performers often brave the cold, providing free entertainment as you stroll around. Don’t forget to grab some hot cocoa or mulled wine from one of the many vendors.

Shopping:  Faneuil Hall Marketplace is also a shopping destination. The area is dotted with a variety of shops, from major retail chains to quirky, independent boutiques. Whether you’re looking for souvenirs, fashion, or unique crafts, you’re likely to find it here.

Food: One of the main attractions of visiting Faneuil Hall is the food. Quincy Market, located just behind Faneuil Hall, is home to a bustling food court that offers an extensive range of options, from classic New England dishes like clam chowder and lobster rolls to international cuisine. It’s a fantastic place to grab a quick, affordable meal in the heart of the city. Outside, in the North and South Markets, you’ll find even more dining options, including sit-down restaurants and pubs where you can take a breather and soak in the atmosphere.

Winter events: Faneuil Hall is not just a summer attraction; it has a year-round appeal. In winter, it transforms into a festive wonderland complete with holiday decorations and seasonal events like the “Blink!” light and sound show. There’s often a large Christmas tree, making it a focal point for holiday celebrations in Boston.

20. Catch a Celtics Game

The best things to do in Boston in winter

Sports are a big deal in Boston, and winter is basketball season. Catching a Celtics game at TD Garden is an electrifying experience and a perfect way to escape the winter chill. The crowd is passionate, and the energy is high, making it one of the best indoor activities in Boston in winter.

The Celtics play right at TD Garden, which is super centrally located and is also North Station (perfect if you’re taking the train in or out). So you can catch a game and do a few other activities if you plan right!

If you’re not from the Massachusetts area, then I highly recommend seeing a Celtics game. There’s nothing like the New England sports atmosphere (we’re pretty intense) and the whole thing is a wild experience.

19. See The Nutcracker Ballet

The best things to do in Boston in winter

When it comes to cultural activities that capture the magic of Boston in winter, seeing a performance of “The Nutcracker” ballet is near the top of the list. Performed annually by the esteemed Boston Ballet and various other local companies, this classic Tchaikovsky ballet has become a cherished holiday tradition for many Bostonians and visitors alike.

The primary venue for the Boston Ballet’s rendition of “The Nutcracker” is the historic Boston Opera House, located in the heart of the Theater District. The Opera House itself is worth a visit, boasting grand architecture and opulent interiors that set the stage for a night of elegance and enchantment. It’s one of the fanciest spots in Boston!

Tickets for “The Nutcracker” typically go on sale in the late summer or early fall and can sell out quickly, especially for popular dates close to Christmas. It’s advisable to book your tickets well in advance. The ballet usually runs from late November through December, offering multiple performances each week, including matinees that are perfect for families. Even if you’re not a huge fan of the ballet, I highly recommend going to see the Nutcracker just to experience the Opera House atmosphere! Plus, you get to dress up, which you won’t find many other places in Boston (it’s a casual city, especially in the chilly winter months).

18. Walk The Freedom Trail

The best things to do in Boston in winter

Boston in winter offers a unique opportunity to walk the Freedom Trail with fewer crowds. The 2.5-mile trail takes you through 16 historical sites, offering a glimpse into America’s past. While it may be chilly, a winter walk along this route offers a quieter, more reflective experience.

Many of the sites, like the Massachusetts State House, Paul Revere’s House, and the Old North Church, are just as captivating in winter. Some of them have indoor areas where you can escape the cold for a bit while learning about the American Revolution and Boston’s role in it.

To enjoy the Freedom Trail in winter, it’s essential to dress warmly. Layering is key, as are waterproof boots, gloves, and a hat. Boston winters can be quite cold, with temperatures often dropping below freezing, especially in the evenings. I recommend insulated snow boots that are easy to walk in and a puffer coat, or at the very least a heavy wool coat with layers. But make sure to check the weather before you go: Boston in the winter fluctuates like crazy!

You can do the trail yourself since it’s pretty easy, but you won’t get much info about the history of the buildings. If you’re a history buff, I recommend doing a guided tour, which in my mind is worth it, but then again I’m obsessed with Boston History!

Check out some of the top tours here.

17. Go Museum Hopping

The best things to do in Boston in winter

Boston is home to a wide range of museums that cater to all kinds of interests, from art and history to science and technology. If you’re looking to engage in a cultural exploration of the city, museum hopping is a great way to do it. Here’s a brief rundown of some must-visit museums and what you can expect at each.

Museum of Fine Arts (MFA)

The best things to do in Boston in winter

What to Expect: The MFA is one of the largest and most comprehensive art museums in the U.S. It boasts an extensive collection that spans multiple continents and centuries, from Ancient Egypt to modern American art.

Details: Located in the Fenway-Kenmore neighborhood, it’s accessible via the Green Line’s Museum of Fine Arts stop. General admission is $25 for adults, but there are discounts for seniors, students, and youth.

Isabella Stewart Gardner Museum

The best things to do in Boston in winter

What to Expect: This museum offers a unique blend of art, architecture, and horticulture. The Venetian-style palace surrounds a beautiful courtyard garden.

Details: It’s a short walk from the MFA, so you can easily visit both in one day. Admission is $20 for adults, and if your name happens to be Isabella, you get in for free!

The New England Aquarium

The best things to do in Boston in winter

What to Expect: This is a must-visit for marine life enthusiasts. Highlights include a giant ocean tank, a penguin exhibit, and a variety of hands-on activities.

Details: Located on the Central Wharf, it’s easily accessible from the Blue Line’s Aquarium station. Tickets are around $32 for adults and $23 for children.

Museum of Science

The best things to do in Boston in winter

What to Expect: A perfect destination for families or anyone interested in science and technology. The museum offers interactive exhibits on topics like physics, biology, and astronomy.

Details: Situated near the Charles River, you can get there via the Green Line’s Science Park/West End station. General admission starts at $29 for adults and $24 for children.

The USS Constitution Museum

The best things to do in Boston in winter

What to Expect: This maritime museum offers an in-depth look at the history of the USS Constitution, the world’s oldest commissioned naval vessel still afloat.

Details: Located in the Charlestown Navy Yard, it’s a bit of a trek but worth it for history buffs. Admission is by donation, so you pay what you can.

The Institute of Contemporary Art (ICA)

The best things to do in Boston in winter

What to Expect: If modern art is more your style, the ICA is the place to go. The museum features rotating exhibits of contemporary artists and offers stunning harbor views.

Details: Situated in the Seaport District, it’s accessible via the Silver Line’s Courthouse station. Admission is $15 for adults, and free for everyone on Thursdays from 5 to 9 p.m.

Boston Children’s Museum

The best things to do in Boston in winter

What to Expect: This is an ideal spot if you’re museum-hopping with younger kids. The museum is designed to be interactive and educational, with exhibits on everything from science and culture to environmental awareness.

Details: Located on Children’s Wharf along Fort Point Channel, it’s close to the Red Line’s South Station. Admission is $18 per person, but they offer $1 admission every Friday from 5 to 9 p.m.

16. Winter Food Tour

The best things to do in Boston in winter

When it comes to experiencing Boston in winter, food is an essential part of the journey. The city’s culinary scene offers a blend of traditional New England fare and innovative cuisine that can warm you up on the coldest winter days. Here’s how to go on a winter food tour in Boston, featuring some iconic foods and where to find them.

New England Clam Chowder

The best things to do in Boston in winter

What to Expect: A creamy, hearty soup filled with clams, potatoes, and onions. It’s a quintessential comfort food for Boston in winter.

Where to Go: Legal Sea Foods in the Seaport District or Quincy Market is a popular choice for an authentic bowl of clam chowder.

Lobster Roll

The best things to do in Boston in winter

What to Expect: Fresh lobster meat served in a grilled, buttered roll. It’s a luxurious treat that’s delicious year-round.

Where to Go: Neptune Oyster in the North End is well-known for its high-quality lobster rolls, albeit at a premium price.

Boston Cream Pie

The best things to do in Boston in winter

What to Expect: A two-layer sponge cake filled with cream and topped with chocolate glaze. It’s so iconic, it’s the official dessert of Massachusetts.

Where to Go: The Omni Parker House in Downtown Boston is where this dessert was invented, so it’s a must-visit for the real deal.

Baked Beans

The best things to do in Boston in winter

What to Expect: Navy beans slow-cooked with molasses and pork. It’s an old-school dish that’s rich in flavor and history.

Where to Go: Durgin-Park in Faneuil Hall used to be the go-to, but since it’s closed, you can head to places like Union Oyster House for a traditional take on this dish.


The best things to do in Boston in winter

What to Expect: A crispy pastry tube filled with sweet ricotta cheese, often garnished with chocolate chips or pistachios.

Where to Go: Mike’s Pastry or Modern Pastry in the North End are both famous for their cannolis and usually have lines out the door, even in winter.

Roast Beef Sandwich

The best things to do in Boston in winter

What to Expect: Thinly sliced roast beef piled high on an onion roll, usually accompanied by BBQ sauce, mayonnaise, and cheese.

Where to Go: Kelly’s Roast Beef in Revere Beach is an institution for this local favorite.

Sam Adams Beer

The best things to do in Boston in winter

What to Expect: While not a food, no trip to Boston is complete without trying a locally brewed Sam Adams.

Where to Go: The Sam Adams Brewery in Jamaica Plain offers tours and tastings, perfect for warming up on a cold winter day.

If you want to get going on your food tour earlier in the day, then try out a classic Boston brunch. There are tons of breakfast spots in Boston and this is a huge event during weekend winter days!

15. Harbor Cruise

The best things to do in Boston in winter

Believe it or not, harbor cruises aren’t just for summer. Some operators offer winter wildlife cruises, a unique way to experience Boston in winter. You’ll have the opportunity to see seals, sea birds, and the breathtaking skyline, all while bundled up and sipping hot tea or coffee.

Several companies offer a variety of harbor cruises, even during winter. Whether you’re interested in history, sightseeing, or just enjoying the sea air, there’s likely a cruise for you. Some popular options include:

Most of the winter cruises leave from Long Wharf or Rowes Wharf, both of which are easily accessible via public transportation. If you’re driving, parking is available but can be pricey.

During the holiday season, some companies offer special-themed cruises, such as New Year’s Eve cruises with fireworks or Valentine’s Day cruises for couples. These tend to sell out quickly, so booking well in advance is recommended.

14. Visit the Boston Tea Party Ships & Museum

The best things to do in Boston in winter

The Boston Tea Party Ships & Museum is not your typical museum experience. You’ll have the opportunity to participate in reenactments, explore authentically restored tea ships, and even throw replica tea crates into the harbor just like the Sons of Liberty did back in 1773.

The museum has a series of exhibits and interactive displays that offer insights into the events, people, and ramifications of the Boston Tea Party. One highlight is the “Eleanor,” one of the museum’s restored ships where you can experience firsthand what it was like to be part of the protest.

The museum is located on Congress Street Bridge in Boston, just a short walk from the South Station, making it easily accessible via subway, bus, or even a leisurely stroll if you’re already downtown.

While the museum is indoors, the ship exhibits can get chilly in winter, so dress warmly. But the wintertime also tends to be less crowded, so you can explore at a more relaxed pace.

Adult tickets are around $30, and discounts are available for children, seniors, and military personnel. Operating hours can vary by season, so it’s best to check the official website for the most current information.

13. Brewery Hopping

The best things to do in Boston in winter

Boston isn’t just famous for its historic sites and seafood; it’s also a burgeoning hub for craft beer enthusiasts. Brewery hopping is an excellent way to get a feel for the local scene, and doing it in winter gives you an excuse to sample some of the darker, richer brews that pair well with chilly weather.

Boston breweries offer a wide range of beers, from hoppy IPAs to robust stouts. In winter, you’ll find seasonal offerings with flavors like cinnamon, ginger, and chocolate. Many breweries also have indoor taprooms and even fire pits to help you shake off the cold.

Samuel Adams Brewery

What It’s Known For: Being one of the pioneers of the American craft beer movement.

Winter Specials: Look out for winter lagers and seasonal ales.

Location: The brewery is located in Jamaica Plain, and they offer tours and tastings.

Harpoon Brewery

What It’s Known For: Their flagship Harpoon IPA and a wide variety of other styles.

Winter Specials: Try their Winter Warmer, a spiced ale that’s perfect for the season.

Location: Located in the Seaport District, they also have a beer hall where you can pair a fresh pretzel with your brew.

Trillium Brewing Company

What It’s Known For: Innovative, high-quality beers, including hop-forward and experimental brews.

Winter Specials: Seasonal stouts and barrel-aged offerings.

Location: They have multiple locations, but the Fort Point location is a popular choice.

Dorchester Brewing Company

What It’s Known For: A focus on traditional styles, as well as some fun experimental brews.

Winter Specials: Expect darker, richer brews during winter.

Location: Located in Dorchester, this brewery also has a spacious taproom.

Night Shift Brewing

What It’s Known For: A wide range of unique and flavorful beers.

Winter Specials: They often release special brews during the holiday season.

Location: Their taproom is in Everett, a short drive from downtown Boston.

12. Beacon Hill Exploration

The best things to do in Boston in winter

Beacon Hill, with its gas-lit streets and Federal-style row houses, is one of Boston’s most iconic neighborhoods. Exploring it in winter adds a layer of charm that makes it feel like you’ve stepped into a real-life snow globe.

In winter, the snow adds a picture-perfect touch, especially in the evenings when the gas lamps are lit. You’ll feel like you’ve stepped back in time.

Start your exploration with a visit to the Massachusetts State House, recognizable by its gleaming golden dome. While the exterior is impressive in its own right, the interior is open to the public and offers historical and architectural intrigue.

One of the most photographed streets in the U.S., Acorn Street is particularly enchanting in winter. The cobblestones and historic homes take on a magical quality when dusted with snow.

This is Beacon Hill’s main thoroughfare, filled with boutique shops, cafes, and antique stores. It’s a great place to grab a hot chocolate or a warm meal. In winter, many of the shops have festive window displays.

Lastly, Beacon Hill is adjacent to Boston Common, the oldest public park in the U.S. In winter, the park is transformed into a winter wonderland, complete with ice skating at Frog Pond.

11. Attend a Boston Pops Concert

The best things to do in Boston in winter

When it comes to cultural experiences in Boston, attending a Boston Pops concert ranks high on the list. The Pops are renowned for their blend of classical music and popular tunes, and there’s no better time to experience their magic than during the winter season, especially around the holidays.

The Boston Pops Orchestra, usually just called the “Pops,” is famous for making orchestral music accessible to the general public. In winter, their repertoire often includes holiday classics, traditional pieces, and even some contemporary hits. It’s not uncommon to hear Tchaikovsky’s “Nutcracker Suite” one moment and a jazzy rendition of a holiday pop song the next.

Conducted in the historic Symphony Hall, decorated to the hilt with festive ornaments and lights, the atmosphere is nothing short of magical. The Holiday Pops concerts often feature sing-alongs, special guest appearances, and even a visit from Santa Claus.

Located in Boston’s Back Bay area, Symphony Hall is considered one of the world’s best concert halls, acclaimed for its superb acoustics. The grand interior, with its intricate moldings and chandeliers, adds a sense of occasion to any concert. This is one of the must-see shows in Boston during winter!

10. Hot Chocolate Tour

The best things to do in Boston in winter

What’s better than hot chocolate in winter? Not much! Boston has several cafes known for their delicious hot cocoa. Take a self-guided tour or just visit a few places to find your favorite hot chocolate in Boston in winter. Some of my personal favorite spots include:

L.A. Burdick Chocolate

What It’s Known For: Their “Drinking Chocolate” is made from shavings of real chocolate rather than cocoa powder.

Location: Located in the heart of Harvard Square in Cambridge, it’s easily accessible via the Red Line.

Tip: This place is often busy, especially on weekends, but the wait is worth it.

Flour Bakery + Cafe

What It’s Known For: A traditional hot chocolate that hits all the right notes—rich, creamy, and perfectly sweet.

Location: They have multiple locations, but the one in the South End is particularly cozy.

Tip: Pair your hot chocolate with one of their mouth-watering pastries.

Caffè Nero

What It’s Known For: Italian-style hot chocolate, which is on the thicker side and can be customized with flavored syrups.

Location: Multiple locations throughout Boston, including Back Bay and Downtown Crossing.

Tip: Opt for the whipped cream on top; you won’t regret it.

Tatte Bakery & Café

What It’s Known For: Offering a decadent “Nutella Hot Chocolate.”

Location: With locations in Beacon Hill and Kendall Square among others, it’s easy to incorporate into your Boston itinerary.

Tip: This spot is also known for its pastries, so consider a combo for the ultimate treat in a French-style cafe.

Thinking Cup

What It’s Known For: Their Valrhona Hot Chocolate is made from Valrhona chocolate and steamed milk.

Location: Conveniently situated along the Freedom Trail, near Boston Common.

Tip: This café also specializes in coffee, so it’s a good option if your group is split between coffee and hot chocolate lovers.

Max Brenner

What It’s Known For: A chocolate-focused restaurant offering an entire menu of hot chocolate variations.

Location: Located in the Back Bay area.

Tip: Try their “Mexican Spicy Hot Chocolate” for something a little different.

9. Boston Winter Village

The best things to do in Boston in winter

This seasonal pop-up features a mix of shopping, dining, and entertainment, all designed to celebrate Boston in winter. Think of it as a winter fair with a variety of activities, from ice maze explorations to shopping for winter apparel.

Imagine twinkling lights, holiday decorations, and the buzz of holiday shoppers all set to the soundtrack of classic winter songs. That’s Boston Winter Village for you. A mix of local artisans, food vendors, and various activities make this a one-stop destination for winter fun.

The village is populated by a variety of kiosks and small pop-up shops, many of which feature local artisans and makers. From handcrafted jewelry to unique Boston souvenirs, there’s a little something for everyone on your gift list. And winter treats are aplenty here. From hot chocolate and mulled wine to food trucks serving up seasonal favorites like roasted chestnuts, the Boston Winter Village is a foodie’s paradise.

One of the highlights is usually an outdoor skating rink. Even if you’re not a skater, it’s fun to watch others take to the ice. Rentals are available, so you don’t have to lug your own skates around the city.

Weekends often feature live entertainment, ranging from local school choirs to professional musicians. The vibe is festive, adding an extra layer of holiday cheer to your visit.

Boston Winter Village is usually set up in a central downtown location, often near City Hall Plaza, making it easily accessible by public transportation. If you’re already downtown for other activities, it’s a convenient stop.

8. Check Out One of Boston’s Famous Speakeasies

The best things to do in Boston in winter

Boston has a rich history that stretches back to the days of Prohibition, and its modern-day speakeasies pay homage to this clandestine era. These speakeasies are all the rage in Boston right now, and are super popular (and cozy!) spots in the winter.


What It’s Known For: Despite its simple name, Drink offers a complex cocktail experience with bartenders who are more like mixologists.

Location: Situated in the Fort Point neighborhood, near the Seaport.

Tip: There’s no menu here; you tell the bartender what you like, and they whip up a custom cocktail for you.


What It’s Known For: Yvonne’s offers an opulent experience with a modern twist on the classic supper club. The atmosphere is a mix of vintage and trendy, featuring intricate chandeliers and plush seating, making it a stylish take on the speakeasy concept.

Location: Situated in Downtown Crossing, just a short walk from the T station.

Tip: Don’t just stick to drinks; their small plates menu is well worth exploring. The “Grilled Lollipop Lamb Chops” and the “Baked Oysters” are must-tries.


What It’s Known For: This place is famous for its creative cocktails and laid-back atmosphere.

Location: Tucked away in Union Square in Somerville, just a short trip from downtown Boston.

Tip: The entrance is a bit hidden, situated at the back of a hallway behind a café. Look for the door marked “Backbar.”

Wink & Nod

What It’s Known For: A sultry, underground lounge setting with plush seating and mood lighting.

Location: In the South End, accessible via the Orange Line at Back Bay Station.

Tip: They frequently rotate their food menu by hosting different chefs, making each visit unique.

The Hawthorne

What It’s Known For: An upscale speakeasy that feels like someone’s stylish living room, complete with bookshelves and comfy chairs.

Location: In Kenmore Square, easily accessible from the Green Line.

Tip: Their cocktail menu is extensive but don’t skip their small bites, which are just as impressive.

Brick & Mortar

What It’s Known For: This speakeasy focuses on classic cocktails with a modern twist.

Location: Located above Central Kitchen in Cambridge’s Central Square.

Tip: The entrance isn’t obvious; it’s an unmarked door next to a hardware store.


What It’s Known For: Not quite a speakeasy in the traditional sense, but its basement location and vintage vibe give it a hidden-away feel.

Location: Nestled in the downtown area, close to Park Street Station.

Tip: Try their signature comfort foods like mac and cheese.

7. Visit the Public Library

The best things to do in Boston in winter

When people think about things to do in Boston in winter, visiting a library might not be the first thing that comes to mind. However, the Boston Public Library is no ordinary library; it’s a historic landmark, an architectural wonder, and a cozy sanctuary all rolled into one.

The Boston Public Library isn’t just a place to read or borrow books. It’s home to stunning architecture, historical collections, rotating exhibits, and even a café. The library offers a tranquil escape from the bustling city outside, making it a perfect spot for a quiet afternoon.

Seriously, if you’re a fan of dark academia, then you’ll want to check out the Boston Public Library simply because it’s gorgeous! Boston is a collegiate historical city and that’s clearly reflected here.

The McKim Building, the older part of the library, is known for its grandeur and Renaissance Revival architecture. When you walk into Bates Hall, you’ll be stunned by the high, coffered ceiling, the rows of green-shaded lamps, and the sense of tranquility that pervades the room.

The modern counterpart to the McKim Building, the Johnson Building is all about contemporary comforts. It’s bright, open, and home to a variety of resources, including computers, an expansive children’s library, and popular fiction and non-fiction titles.

The Boston Public Library’s main branch is located in Copley Square, easily accessible by taking the Green Line to Copley Station.

6. Shop on Newbury Street

The best things to do in Boston in winter

If you find yourself in Boston in winter and have a penchant for shopping, you absolutely must stroll down Newbury Street. Known as Boston’s most famous shopping street, Newbury has a little bit of everything—from high-end boutiques to popular chains, vintage stores, and even some cute cafés for when you need a shopping break.

Newbury Street is a shopper’s paradise. It’s home to a variety of retail experiences, ranging from luxury brands like Chanel and Gucci to local boutiques that offer something uniquely Bostonian. You’ll also find home decor shops, bookstores, and plenty of beauty and skincare options.

The atmosphere is part of what makes shopping on Newbury Street so enjoyable. Cobblestone sidewalks, historic brownstones, and trees strung with fairy lights make it a charming place to be, even more so when there’s a blanket of snow on the ground.

All that shopping can make you hungry. Luckily, Newbury Street has an array of food options. Grab a quick bite from a food truck, settle in for some fine dining, or warm up with a hot drink from one of its many cozy cafés.

Even if you’re not a big shopper, I recommend that you walk down Newbury Street and enjoy the atmosphere. This is one of the prettiest spots in Boston in the winter!

5. Take a Tour

The best things to do in Boston in winter

Boston is a city rich in history, culture, and stunning sights that can be enjoyed all year round. If you’re visiting Boston in winter, taking a guided tour can provide you with a deeper understanding and appreciation of the city’s many attractions. Here are some of the best tours to consider when you’re in Boston during the colder months:

Freedom Trail Tour

The best things to do in Boston in winter

What It Is: A guided tour along the 2.5-mile-long Freedom Trail that takes you through 16 historical sites.

Why It’s Great in Winter: The winter snow adds an extra layer of charm to this historic walk. Just bundle up and maybe grab a hot cocoa beforehand!

Trolley Tour

The best things to do in Boston in winter

What It Is: A hop-on, hop-off trolley service that covers Boston’s major attractions.

Why It’s Great in Winter: It’s a quick way to see the sights without spending too much time in the cold. Some even have heated trolleys!

Harbor Cruise

The best things to do in Boston in winter

What It Is: A boat tour that gives you fantastic views of the Boston skyline and harbor area.

Why It’s Great in Winter: While many harbor cruises run only in warmer months, some specialty winter cruises offer breathtaking views of the snowy cityscape.

Brewery Tour

The best things to do in Boston in winter

What It Is: Visit some of Boston’s best breweries to learn about the beer-making process and sample some local brews.

Why It’s Great in Winter: A brewery tour is an indoor activity, making it perfect for a chilly day. Plus, many breweries offer seasonal winter ales.

Haunted Boston Ghost Tour

The best things to do in Boston in winter

What It Is: This evening walking tour takes you through some of Boston’s most haunted sites while telling tales of the city’s eerie past.

Why It’s Great in Winter: The early sunset and chilly weather add to the spooky atmosphere.

Fenway Park Tour

The best things to do in Boston in winter

What It Is: A behind-the-scenes tour of Boston’s iconic baseball stadium.

Why It’s Great in Winter: While there’s no baseball in winter, the stadium tour is still available and much less crowded.

Food Tour of the North End

The best things to do in Boston in winter

What It Is: Sample some of Boston’s best Italian food as you stroll through its oldest neighborhood.

Why It’s Great in Winter: The hearty Italian fare will warm you up in no time.

4. See the Tree Lightings

The best things to do in Boston in winter

One of the most festive activities to do in Boston in winter is attending one of the many tree-lighting ceremonies. The city is home to several grand trees that are illuminated in spectacular fashion. From the ceremony at Boston Common to others in different neighborhoods, it’s a twinkling way to ring in the holiday season.

3. Skiing and Snowboarding

The best things to do in Boston in winter

If you’re a winter sports enthusiast, you’ll be thrilled to know that Boston in winter offers relatively easy access to a variety of skiing and snowboarding options. While the city itself doesn’t have ski slopes, there are several excellent resorts and mountains within a couple hours’ drive. Here are some of the best spots to consider:

Wachusett Mountain

Location: About an hour and a half from Boston.

What’s Special: A solid mix of beginner, intermediate, and advanced runs. They also have night skiing, so you can hit the slopes after the sun sets.

Loon Mountain

Location: Around two hours north in New Hampshire.

What’s Special: Known for its expansive terrain and excellent snow conditions. It’s bigger than many of the closer resorts, offering a broader range of trails.

Sunapee Mountain

Location: Also about two hours away, in New Hampshire.

What’s Special: Sunapee is great for families and offers a balanced variety of trails for skiers and snowboarders of all levels.

Blue Hills Ski Area

Location: Just 30 minutes from downtown Boston.

What’s Special: While it’s smaller and has less challenging runs, it’s the closest option for a quick day trip to scratch that skiing itch.

If you’d prefer to go for a weekend, there are plenty of awesome mountains in New Hampshire, Vermont, and Maine that are a few hours’ drive.

2. Go Sledding

The best things to do in Boston in winter

When the first big snowfall hits, one of the simplest and most enjoyable winter activities in Boston is sledding. Grab your sled, or even a cafeteria tray if you’re a college student looking for a cheap thrill, and head to one of the city’s many parks that become sledding havens in the winter. Here are some top spots to consider:

Boston Common

Location: Central Boston

What’s Special: This iconic park offers multiple hills suitable for all age groups. The Frog Pond area is a popular sledding spot, offering easy slopes for younger kids.

Larz Anderson Park

Location: Brookline

What’s Special: Known for having one of the largest and steepest hills in the Boston area, it’s perfect for those looking for a little more speed and excitement.

Arnold Arboretum

Location: Jamaica Plain

What’s Special: This park is ideal for sledding among beautiful, snowy trees. The sloping terrain provides plenty of options for sledders of various skill levels.

Prospect Hill Park

Location: Waltham

What’s Special: With multiple hills and an incredible view of the Boston skyline, Prospect Hill offers a sledding experience that’s both fun and scenic.

1. Visit Nearby Small Towns

The best things to do in Boston in winter

One of the cool things about being in Boston in winter is that you’re not far from some quintessentially New England small towns that look like they’re straight out of a holiday card. A quick drive can transport you to charming locales where you can experience a different, more relaxed vibe. Here are a few spots worth the trip:


Location: About 30 minutes north of Boston.

What’s Special: Known for its witch trials, Salem offers history, museums, and a charming downtown area. In winter, the crowds are smaller and the vibe is cozier. See the top things to do here, as well as some awesome Salem restaurants here.


Location: Roughly 30 minutes west of Boston.

What’s Special: The town is rich in literary history, being the home of authors like Thoreau and Emerson. Walden Pond is particularly peaceful in the winter months.


Location: About an hour north of Boston.

What’s Special: This coastal town is beautiful in winter. With fewer crowds, you can really enjoy the boutiques and seafood restaurants at a leisurely pace. Plus, Newburyport offers some cozy, historic hotels that you won’t want to leave!

Check out our favorite things to do in Newburyport here, and our top Newburyport restaurants here.


Location: An hour and a half north of Boston.

What’s Special: Known for its art galleries and Bearskin Neck, a scenic stretch of old fishermen’s shanties converted into shops, Rockport offers a serene oceanfront experience in winter with plenty of things to do and delicious restaurants.

FAQs About Visting Boston In Winter:

Just how cold does Boston get in the winter?

Boston winters can vary, but they’re generally cold. Temperatures can range from mild to quite chilly. Here’s a general idea:


  • Average High: Around 41°F (5°C)
  • Average Low: Around 28°F (-2°C)


  • Average High: Around 36°F (2°C)
  • Average Low: Around 22°F (-5°C)


  • Average High: Around 39°F (4°C)
  • Average Low: Around 25°F (-3°C)

Snowfall is also common, especially in January and February. The city can receive anywhere from a light dusting to several inches of snow in a single storm.

Wind chill can also be a factor, making it feel colder than the actual temperature. It’s not unusual to have days where the wind chill dips into the single digits or even below zero in Fahrenheit, particularly in January and February.

Basically, Boston in the winter is pretty chilly. It won’t be as cold as, say, Canada, but you will want to bring tons of layers. Even for a night out at a bar, everyone will be dressed in sweaters.

What should I pack for Boston in the winter?

Boston in winter is chilly, often snowy, and sometimes downright freezing. But that doesn’t mean you have to sacrifice style for warmth. Here’s how you can look chic while braving the Boston cold:


Wool Coat: Go for a classic wool coat that reaches at least down to your thighs. Black, navy, or camel tones are versatile and timeless.

Puffer Jacket: For especially cold days, a sleek puffer jacket can be both warm and stylish. You’ll see a lot of long puffer coats in Boston, usually in darker colors.


Leather or Suede Boots: Knee-high or ankle boots with a good grip are perfect for navigating the city streets.

Sneakers: A pair of stylish yet functional sneakers can be great for days when you’ll be doing a lot of walking but the weather is dry.

Snow Boots: Of course, you’ll see plenty of snow boots in Boston. I love a good low pair of snow boots that are cute and comfortable.


Sweaters: Pack a variety of knits, from chunky turtlenecks to slim cashmere pullovers. We pretty much wear sweaters everywhere in Boston in the winter, from museums to pubs.

Long-Sleeve Tees: These are great for layering under sweaters and jackets. Stick to neutral colors to maximize outfit combinations.


Beanie or Fedora: A cute hat can keep you warm while also upping your style quotient. I personally wear a knit beanie everywhere I go – this is a staple.

Scarf: Go for a large, cozy scarf that can double as a wrap. Plaid or herringbone patterns can add some texture to your look and are pretty common.

Leather Gloves: They’re warmer than you think and way more stylish than chunky knit ones. This is the “upscale chic” city vibe for Boston in winter.

Lastly, you’ll want to bring nice sunglasses and simple jewelry. You’ll see most people wearing leggings or jeans tucked into boots just about everywhere, though you can get away with a tweed skirt and tights if the weather is more mild.

Guys tend to dress pretty casual and preppy, with simple jeans, workboots or snowboots, henleys, puffer coats, or wool coats (when they’re feeling fancy).

Is Boston walkable in the winter?

Boston is definitely a walkable city, even in the winter months. The compact layout of the city makes it convenient to go from one neighborhood to another on foot, and many attractions are clustered close together.

Boston gets its fair share of snow, and while the city is generally good at clearing main roads, you might find some smaller streets and sidewalks that are icy or slushy. Be careful when walking, and it’s advisable to wear boots with good grip.

Also, daylight is limited during winter; the sun sets as early as 4:30 p.m. in the deepest winter months. If you plan to walk around, either make the most of the daylight hours or stick to well-lit areas if you’ll be out in the evening.

Boston’s public transportation system, known as the “T,” is generally reliable and can be a great way to cover longer distances or to give yourself a break from the cold. Just be aware that inclement weather can sometimes cause delays. So plan in about 30 minutes anytime you want to take the T, even if it’s supposedly a short jump (there’s almost always at least one delay).

While Boston is walkable, it’s worth noting that it’s also an old city with cobblestone streets, which can be a bit tricky to navigate in icy conditions. If you or someone in your group has mobility issues, extra caution will be needed. And you won’t want to wear heels

Cozy Boston Hotels During The Winter:

When you’re visiting Boston in winter, a cozy hotel can make all the difference. Nothing beats returning to a warm, inviting space after a day of exploring the chilly city. Here are some hotels that offer that extra level of coziness you’ll crave during your winter getaway.

The Liberty Hotel

The best things to do in Boston in winter

Location: Beacon Hill
What’s Special: Situated in a converted jail, The Liberty offers a unique blend of historical charm and modern luxury. With warm fireplaces in the lobby and plush bedding, it’s a cozy spot to unwind.

XV Beacon

The best things to do in Boston in winter

Location: Beacon Hill
What’s Special: This boutique hotel takes luxury to the next level. Each room features a fireplace, and you’ll have access to complimentary hot chocolate and warm cookies in the lobby.

Boston Harbor Hotel

The best things to do in Boston in winter

Location: Waterfront
What’s Special: Want to enjoy waterfront views without braving the cold? The Boston Harbor Hotel offers just that. Its rooms are designed to make the most of the views while keeping you snug and warm.

Omni Parker House

The best things to do in Boston in winter

Location: Downtown
What’s Special: Known as the longest continuously operating hotel in the U.S., Omni Parker House has a rich history and classic New England charm. It’s famous for its Parker House Rolls and Boston Cream Pie.

The Lenox

The best things to do in Boston in winter

Location: Back Bay
What’s Special: Sustainability meets luxury at The Lenox. The hotel features eco-friendly amenities, but what makes it a winter haven are the real wood-burning fireplaces in some rooms.

So, there you have it—a comprehensive guide to making the most out of Boston in winter. Despite the cold and snow, this historic city has a unique charm that truly comes alive during the winter months. From festive tree lightings and holiday markets to world-class museums and cozy hideaways, Boston offers a multitude of experiences that cater to all kinds of interests.

Visiting Boston in winter lets you see the city in a different light—literally and figuratively. The shorter days make the city lights glow brighter, and the snow-draped architecture turns familiar landmarks into postcard-worthy scenes. Yes, it’s cold, but with the right gear and a hearty New England spirit, you’ll find the city to be just as welcoming in winter as in any other season.

So, if you’re wondering whether to visit Boston in winter, the answer is a resounding yes. With a little preparation and an open mind, you’ll find that Boston’s winter offerings are as rich and rewarding as those of any other season. Get ready to layer up, step out, and dive into a winter wonderland like no other!

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