Things to Do In Boston in the Winter
Winter in Boston is serious business: cold maritime winds that can scrape your skin off if you’re not dressed appropriately and prepared for extreme weather. With lows bouncing just north of the low teens in January, you’ll need to pack layers of clothing while visiting Boston during the winter months. As someone who has visited Boston many times during the winter, don’t let this discourage you from visiting. Winter in Boston can be glorious if you just spend some time preparing for your visit.
It’s hard to beat snow on brownstones. Typically, Boston will see snowfalls throughout the entire winter with a handful of power storms dumping massive amounts of snow 3-4 times per year. One year, I saw piles of snow in Boston hanging on in May. If you’re looking for some sledding options, you might want to try Boston Commons, Flagstaff Hill or Gore Place. If you’re a history buff, learn more about the summer of 1816 when it snowed in Boston.
If you visit during the holidays, there are a few must-see destinations: the Museum of Fine Art’s Festival of Lights, tree lighting ceremonies throughout town, Hanukkah celebrations at Faneuil Hall, and a First Night celebration on New Year’s. We’ll share more information below, but ice skating in Boston is also high on our list. The Boston Common Frog Pond is a local favorite (see photo below).
How to Get Here
Thankfully, Boston’s Logan International airport is world-class and is on the receiving end of hundreds of flights from around the world each day. Overall, you shouldn’t have any problems navigating this airport, but give yourself plenty of time to drive to the airport if you’re on a return or departure flight. At times, the traffic can be a challenge. Also, take it from our experience, document where you park so you can easily find your vehicle later. You might also want to check out renting a campervan or RV to tour the area so you can explore the area in style. Outdoorsy does a good job offering some local, well-priced rental options.
Where to Stay
We have a number of recommendations for Boston. First, check out some of our Boston-based VRBO options:
- Hip Boston 19th-century farmhouse
- Large historic home (accommodates up to 12) near cental Boston
- Very high end, historic home in prime location (accommodates up to 12)
- Charming history (1920s) 2-bedroom apartment (accommodates up to 7)
If you’re unable to find the right fit with a VRBO option, try Expedia to search for a Boston hotel. Two of the most popular hotels in Boston are the Verb Hotel and the Whitney Hotel Boston. Both are top-rated. We recommend the Revolution hotel for the best value.
1. Ice Skating in Boston
The Boston Common Frog Pond in Boston Common is indeed four seasons of family fun, but the winter season is special. Located in the heart of the oldest public park in the country, this beloved location is home to a skating academy and offers skate rentals, camps, clinics, group reservations and a host of other crowd-drawing appeal.
Once you’ve burned a few calories on the ice, check out the Frog Pond Café where you can warm up with some hot chocolate, burgers, fries and fried foods. The rink is open from November through March, and as long as you can keep yourself warm enough, it’s hard to beat the New England vibe you’re sure to enjoy. If you’d like to find an alternative ice skating location, there are many in the area. We’ve listed some additional options below:
- Skate at Canal District Kendall: You can ice skate on this beautiful rink with nearby modern Canal District buildings and light-covered trees. Afterward, you can walk along the Charles River and watch Boston in the distance.
- The Rink at 401 Park: This skating rink is the most contemporary-looking location and not far from the world-famous Trillum Brewing Company.
2. Walk the Freedom Trail
Since the Freedom Trail is only 2.5-miles long, you’ll want to assess how serious the snow (and ice) is before starting the trek. This winding path passes almost 20 of the city’s most important historic sites, including the Massachusetts State House, Old South Meeting House, Old State House, and the site of the Boston Massacre.
The path also leads to Faneuil Hall, a must-see in Boston any time of the year. Ideally, you’ll have at least a few hours here to shop, sit down at a restaurant (or in the food court), and buy a souvenir or two. And of course, spend some time watching the street performers where you’ll enjoy a wide range of shows. Quincy Market, South Market and North Market are all adjacent to each other. TripAdvisor does an excellent job breaking down the Freedom Trail experience if you’re looking for additional information.
3. Fenway Park
No list would be complete without encouraging you to visit Fenway Park. Even when the baseball season isn’t active, you can tour Fenway Park year-round, rain or shine. When we went on a tour, we were thrilled to be given access to so many different parts of this structure while a tour guide shared more about the history of Fenway Park. Since 1912, Fenway Park has been the home of the Boston Red Sox. And..it’s the oldest active ballpark in MLB.
Because of its age and constrained location in Boston’s dense Fenway–Kenmore neighborhood, the park has many unique features, including “The Triangle,” Pesky’s Pole, and the famous Green Monster in left field. Even though it’s the fifth-smallest among MLB ballparks by seating capacity, you’ll enjoy the vibe wherever you sit. For some, they might even find the process of ordering a hotdog or peanuts (as they get passed from person to person) as enjoyable as watching the game itself. Don’t forget to stop by the souvenir shop so you can purchase a Boston RedSox shirt, hat or some other item.
4. Winter Bicycling in Boston
We highly recommend that you take a few minutes to review Bicycle New England’s Bicycling in Boston post where you’ll find information about Boston bicycle trails and bike rentals. Even though winter can be a challenging time to bicycle in Boston, we still recommend considering getting outside on two wheels if the weather is cooperative. You can find some tips about bicycling in Boston on the MassBike site. Make sure you review the Massachusetts bicycle laws before hitting the pavement with your bicycle. If you’re a hardcore cyclist, you may want to check out this Bicycle New England post about preparing your bicycle for winter conditions. You might also want to purchase some bicycling pants that are designed specifically for winter cycling.
5. Boston Museums
There are few cities as well endowed with the kind of variety Boston has when it comes to museums and historical sights. As one of the oldest cities in our country, it’s not surprising that Boston is home to some of the country’s oldest museums. The Boston Tea Party Ships & Museum is one of our favorites and a must-visit destination.
This “museum” is really a large ship that hails from 1773. Period clothing dons the actors who roam the recreated tea ships to educate visitors. Visit on December 16th to catch the annual tea party reenactment.
The Museum of Fine Arts Boston is another top attraction in Boson. Here, visitors can view masterpieces across numerous genres, ranging from ancient Egyptian works of art to modern street art.
if you have younger kids, you may want to consider visiting the Boston Children’s Museum. Explore bubbles in the Science Playground, create something awesome in the Art Lab, or visit a Japanese silk merchant’s home. One of our all-time favorite museums is the Isabella Stewart Gardner Museum. This is an eclectic location with a unique collection of art: 7500 paintings, sculptures, furniture, textiles, silver, ceramics, 1500 rare books, and 7000 archival objects from ancient Rome, Medieval Europe, Renaissance Italy, Asia, the Islamic world, and 19th-century France and America. Among the artists represented in the galleries are Titian, Rembrandt, Michelangelo, Raphael, Botticelli, Manet, Degas, Whistler and Sargent. Netflix even produced a 4-part series about the massive art heist that occurred at this museum. Below are some additional options if you’re in the mood for a visit to the museum:
6. Boston Craft Breweries
Boston is home to some of the most well-known craft breweries in the nation. Trillium Brewery is probably the most well-known with locations across Massachusetts and Connecticut. The Boston-based Trillium location can be found at Fort Point and in the Fenway Park neighborhood. Even though it’s not in Boston proper, our favorite brewery in the area is Treehouse Brewery. Since Treehouse doesn’t really distribute their beer, you’re simply going to have to pay homage to this brewery and log some time at the mothership in Charlton, MA.
Some other Craft Breweries we recommend visiting:
You can read more about each of these breweries at the Thrillist’s detailed craft brewery review for Boston.
7. Watch a Play in Boston
Boston’s main theater district consists of over a dozen venues set right in the middle of downtown. You’ll find Broadway musicals, Christmas performances, dance shows, and just about every other kind of type of entertainment.
The first destination on your list should be the iconic Boston Opera House. Located on Washington Street, this Baroque building is also an architectural sight. During November and December, you’ll find the beloved Nutcracker Ballet, a must-see when visiting Boston over the holiday season. In addition to the performance, enjoy a wonderful pre-show dinner.
The easiest way to find out which performances are available is to visit the Boston-theater.com website where you’ll find the most updated list of upcoming shows.
8. Shop in Boston
Whatever type of shopping adventure you’re looking for, the Prudential Center will almost certainly hit the target. As you meander through the Prudential Center, you’ll find brands such as Saks Fifth Avenue, Ann Taylor, Canada Goose, Lululemon, L’Occitane, and Sephora.
When you’ve worked up a hunger, you’ll also find a number of excellent eateries to help you recharge and prepare for your next shopping foray. The Prudential Center website includes a food directory you can peruse.
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 benedict 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.
Some other shopping options in Boston
- 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.
- Other holiday markets in Boston – A guide by Boston University
9. Watch a Celtics or Bruins Game
It’s easy to get excited while watching a game at the TD Garden. We’re sports fans and couldn’t get enough of the various sporting venues available in Boston. Since we’re focused primarily on winter activities in Boston, we’ll share information here about basketball and hockey. For a more exhausting list of New England sports teams, see the Explore New England directory of sports teams. Don’t forget to throw on some green if you visit a Celtics game!
First, you should know Bostonians are exceptionally proud of their exceptional sports teams. How many NBA teams have won 17 NBA finals? Not many…but the Boston Celtics have. Boston is the official home of Boston Celtics as well as the Boston Bruins. Not surprisingly, TD Garden is the largest sports venue in New England.
Visited by more than 3.5 million people annually, the TD Garden hosts over 200 events a year. Check out the TD Garden website for upcoming events to see if you’re able to purchase tickets. TD Garden has three restaurants or just go with the tried and true event snacks at one of the on-site concessions stands.
10. Hop on an Old Town Boston Trolley Tour
If your legs need a rest, hop on an Old Town Trolley and get ready to see some of the more interesting parts of Boston while you listen to a guide tell stories of happenings long past. We were both amazed and shocked to hear more about the Boston Molasses Flood and to see where this catastrophe occurred during our tour.
Hop off at one of the 19 stops to enjoy restaurants, shops and any number of things to do. Then, hop back on when you’re ready to travel to the next destination. No need to futz around with parking or navigate around snowbanks, let the trolley driver do the hard work while you sit back, relax, and soak up the heat.
11. Boston Holiday Lights
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.
- 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)!
12. Boston Cocktails
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 Roofop 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!
13. 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!
What to Pack for a Winter Visit To Boston
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 of layers and some extremely warm socks. Visit New England Gear Guide for:
- Cold weather sock suggestions
- Water bottles that do well in extreme weather conditions, or;
- Cold weather jackets
The lead photo for this article was taken by Kyle Klein via Greater Boston Convention & Visitors Bureau.