16 Best Things to Do in Boston in Winter

Boston in winter is a magical blend of historic charm, cozy indoor experiences, and outdoor adventures that embrace the season’s chill. Whether you’re looking to skate under the stars, sip on a local brew, or marvel at glittering light displays, the city transforms into a snowy wonderland full of unforgettable moments. Let’s dive into the 16 best things to do in Boston during the winter, complete with all the details to inspire your perfect cold-weather itinerary.

16 Best Things to Do in Boston in Winter

1. Skate on the Frog Pond

Located in the heart of Boston Common, Frog Pond is the ultimate winter wonderland. This iconic outdoor skating rink offers a quintessential Boston winter experience. Glide across the ice surrounded by the beauty of Boston Common’s snowy trees and historic ambiance. Rentals are available, so there is no need to worry if you didn’t pack your skates. Afterward, grab a hot chocolate from the nearby café to warm up. Pro tip: Visit in the evening when the rink is illuminated with twinkling lights for an even more magical atmosphere.

2. Cozy Up Fireside

Winter in Boston calls for cozy moments by the fire. Boston’s historic hotels and restaurants offer roaring fireplaces perfect for a relaxed evening. Try the Liberty Hotel, a former jail-turned-boutique-luxury haven, where the Alibi Bar serves creative cocktails by the fire. Alternatively, sip on mulled wine at Oak Long Bar + Kitchen at the Fairmont Copley Plaza, a historic icon in the city.

3. Warm Up at a Candlelight Concert

Attend a Candlelight Concert in one of Boston’s iconic venues for an elegant and unforgettable evening. These intimate performances feature world-class musicians playing everything from classical masterpieces to modern hits, all in a warm, candlelit setting. Venues like the Old South Church or Boston’s historic libraries make the experience even more enchanting. The acoustics and ambiance create a cozy yet refined way to enjoy winter nights.

4. Enjoy Seasonal Winter Lights

Winter lights transform Boston into a glittering wonderland. From the Boston Common Tree Lighting to illuminated installations at the Public Garden, the city sparkles during the colder months. Visit the Christopher Columbus Waterfront Park, where blue lights sparkle among trellises and pathways, creating a romantic winter stroll. The Seaport’s Snowport also offers creative light displays paired with interactive exhibits.

5. Visit a Winter Market

Boston’s winter markets are perfect for soaking up seasonal cheer and shopping for unique gifts. The Snowsport Winter Village in the Seaport District is a must-visit, offering a mix of artisanal vendors, festive treats, and games like curling. Another favorite is the Boston Winter Market at City Hall Plaza, where local vendors sell handmade crafts, jewelry, and gourmet snacks in a European-style market atmosphere.

6. Enjoy First Night Boston

Ring in the new year at First Night Boston, the city’s largest New Year’s Eve celebration. This free, family-friendly event includes live music, ice sculptures, and a grand fireworks display over Boston Harbor. The festivities start early and run late, making it a fantastic way to wrap up the holiday season in true Bostonian style.

7. Explore Downtown Boston

Winter is an excellent time to explore Boston’s historic downtown. Bundle up and stroll through cobblestone streets in neighborhoods like Beacon Hill, where gas-lit lamps and Victorian architecture look straight out of a holiday postcard. Don’t miss Faneuil Hall Marketplace, which lights up with seasonal decorations and offers local eats to fuel your adventures.

8. Visit Copley Square

Copley Square is a hub of history and culture, and it takes on a serene beauty in the winter months. Snap photos before the iconic Trinity Church, then pop into the Boston Public Library for a warm escape. Their reading rooms offer breathtaking architectural details, and seasonal exhibits add charm.

9. Go Sledding on Boston Common

For classic winter fun, grab a sled and head to the hills of Boston Common. This beloved tradition is perfect for kids and adults, offering a fun way to enjoy the city’s first public park. If you don’t have your sled, stores like Target or nearby shops often carry inexpensive options.

10. Catch a Boston Celtics or Bruins Game

There’s nothing like the energy of a live sports game in Boston. Cheer on the Boston Celtics at TD Garden, or get into the winter spirit with a Boston Bruins hockey match. The fans, the snacks, and the electrifying atmosphere make these games a must for sports enthusiasts and visitors alike.

11. Take a Brewery Tour

Boston is home to a thriving craft beer scene; winter is the perfect time to explore it. Visit legendary breweries like Samuel Adams Brewery for a tour and tasting, or stop by local favorites like Harpoon Brewery, which also features a cozy beer hall and seasonal brews. Don’t forget to try their famous pretzels alongside your winter ale.

12. Tour Fenway Park

Think Fenway Park is only for summer baseball games? Think again! Take a winter tour of Fenway Park, America’s oldest ballpark, to learn about its rich history and get a behind-the-scenes look at this iconic venue. It’s a unique way to experience Boston’s love of sports even when the Sox aren’t playing.

13. Cruise Around Boston Harbor

Winter cruises on Boston Harbor are an underrated gem. Bundle up and take a scenic ride aboard a heated vessel to see the city skyline framed by icy waters. Some cruises even offer themed events, like hot cocoa tastings or brunch cruises, making exploring the waterfront a unique and cozy way.

14. Christopher Columbus Waterfront Park

This picturesque park is a winter delight, especially when draped in blue holiday lights. It’s the perfect spot for a quiet stroll or photoshoot near the North End and Boston Harbor. Pair your visit with a meal at one of the nearby Italian restaurants in the North End for a quintessential Boston experience.

15. Snow Tubing in Amesbury

Amesbury Sports Park offers thrilling snow tubing adventures just a short drive from the city. Perfect for families, couples, or groups of friends, this winter activity lets you zoom down snowy slopes with breathtaking views. Bonus: They offer snowmaking, so you’re guaranteed fun even if Mother Nature doesn’t cooperate.

16. Explore the Arts at the Isabella Stewart Gardner Museum

Winter is the perfect time to explore Boston’s indoor cultural gems, and the Isabella Stewart Gardner Museum is a top pick. Known for its stunning courtyard garden, even in winter, the museum offers a one-of-a-kind collection of art housed in a Venetian-inspired palace. Don’t forget to check out their seasonal exhibits or enjoy a coffee in their serene café.

Conclusion

Boston in winter is an enchanting blend of seasonal activities, historic charm, and cozy experiences. From skating on Frog Pond to discovering the arts at the Isabella Stewart Gardner Museum, there’s something for everyone to enjoy. Whether you’re a local rediscovering the city or a visitor soaking in Boston’s winter magic, these 16 activities promise unforgettable memories.

So pack your warmest layers, grab a cup of hot cocoa, and get ready to explore the best of Boston this winter!