Things to Do in Boston in Winter

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.

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 16^th 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:

• Boston Science Museum
• Boston Institute of Contemporary Art
• Harvard Museum of Natural History
• USS Constitution Museum
• The MuseumsofBoston.org site has a longer list with additional information about Boston museums.

Some other Craft Breweries we recommend visiting:

• Distraction Brewing, Roslindale
• Democracy Brewing
• Turtle Swamp Brewing, Jamaica Plain
• Dorchester Brewing Co.
• Aeronaut Brewery, Somerville
• Winter Hill Brewing Co.
• Jack’s Abby, Framingham
• Cambridge Brewing Co.
• Harpoon Brewing
• Night Shift Brewing
• Notch Brewing, Salem

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.

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

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.

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.