Boston is a city that offers something special during the winter months. With beautiful historic areas, bustling waterfront areas and cultural areas to explore, there are plenty of ways to get into the festive spirit.
Whether you love Boston’s food scene, history and heritage or modern attractions, there are plenty of things to do to make your trip to Boston in the winter really memorable.
Top 10 Ways to Experience Boston in Winter
- Enjoy Boston’s Festive Events – Frostival
Boston hosts a whole 3 months of festive events throughout the winter months with their Frostival. The festival kicks off with a stunning drone show above Boston Common on the 5th, 12th and 19th December 2026. There will be two 15 minute show taking place at 6pm and 8pm each evening with glowing lights and colours inspired by Boston’s landmarks, festivals and festive cheer.
From the 22nd January until the end of February 2027, the Frostival Lodge Furnished by Wayfair will be back in Copley Square offering even more festive fun. There will be quiz nights, bingo nights, acoustic music, games, tea and wine tasting. Plus there will be a full bar with festive drinks and food from select local partners. The Catered Affair will be serving unique weekly menu items, cooking demonstrations and chats.
A brand new 75ft Ferris wheel will be arriving at the Rose Kennedy Greenway in February.
- Skate on Boston Common
No visit to Boston in the winter is complete without a skate around the Frog Pond in the centre of Boston Common. Whether you’re an expert or a beginner, gliding around the rink gives you a true winter experience.
After a while on the ice, head to one of the nearby restaurants for a hot drink and a relaxing stroll around this beautiful historic park.
- Visit the Snowport Market
The Seaport area really comes alive during the winter with the Snowport programme. This includes a festive market, food and drinks, shopping and lots of seasonal fun. You’ll be able to check out independent traders selling handmade decorations and specialty foods.
You’ll also be able to enjoy a little exploration of the restaurants and waterfront in this busy area of Boston. There will be plenty of seasonal events and activities happening throughout the winter. Find out more about the programme here.
- Take a Relaxing Stroll Around Beacon Hill
Beacon Hill is a picture perfect place to visit in the winter. Full of traditional brick houses, gas lamps and lovely restaurants. This area should be visited at a relaxed pace to enjoy browsing the independent stores, bookshops and antique shops.
Charles Street is the perfect place to start your exploration. Beacon Hill Books & Cafe is a lovely place to stop for a coffee and to relax with a good book. Spend an afternoon exploring this beautiful area.
- Enjoy Boston’s Food Scene
Boston has a brilliant food scene to visit during the winter. Offering traditional New England dishes combined with Italian, Coastal Mediterranean, Chinese, Taiwanese, Vietnamese, Portuguese and many more global cuisines.
Whether you want to try some familiar dishes or something new, sitting down in one of Boston’s restaurants is a great way to experience the food culture in the area. If you love eating your way around destinations then Boston is a fantastic place to visit during the winter.
- Visit Museums and Culture
If you’re not keen on being outside in the cold, Boston has some inspiring museums and culture to visit. Spend an afternoon exploring the Museum of Fine Arts or enjoy the unique mix of art and architecture at the Isabella Stewart Gardner Museum.
There are plenty of culture events taking place in Boston throughout the winter with a vibrant performing arts scene.
- Enjoy a Hot Igloo on the Rooftop
Whilst it may be cold outside, some of Boston’s rooftop bars offer hot igloos. These give you somewhere to enjoy a drink and some nibbles whilst enjoying the beautiful skyline views.
The Envoy Hotel has a long tradition of providing this. Get relaxed in a cozy igloo whilst enjoying some drinks and stunning views of the cityscape.
- Enjoy the Magic of The Nutcracker
A great way to enjoy some culture during your winter break is by watching The Nutcracker. Tchaikovsky’s music brings Clara’s Christmas story to life with beautiful choreography, fabulous costumes and stunning set designs.
From dancing snowflakes to the Mouse King, The Nutcracker really captures the magical feeling of the festive period. Held in the beautiful Citizens Opera House, this popular festive event will be running from 27th November until 31st December 2026.
- Explore Boston’s Neighbourhoods
Winter is a great time to explore Boston’s neighbourhoods. From the trendy shops on Newbury Street in Back Bay to the waterfront in the Seaport area there are lots of areas to explore.
As you wander around you’ll see some beautiful historic buildings, modern buildings, independent stores and restaurants. There will be less traffic during the winter so it’s a lovely time to explore on foot and enjoy a relaxed meal.
- Watch a Show or Sport
Boston has lots to offer during the winter. Whether you love watching a show, live music or sport there is something for everyone.
Enjoy your evening even more by having a meal in one of Boston’s many restaurants. Whether you’re visiting a bigger theatre or sport venue or one of Boston’s many varied restaurants there are plenty of ways to enjoy an entertaining evening.
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