How to Spend a Winter Weekend in Boston (That Isn’t Just Museums)

Boston winters may be chilly, but the city doesn’t slow down when the snow starts to fall. If you’re searching for what to do in Boston in winter beyond the usual museum stops, you’ll find plenty of cozy, exciting, and unique activities to fill a two-day getaway. From outdoor adventures to the best indoor activities in Boston, here’s how to plan a winter weekend that’s memorable, social, and warm.

Quick Answer: Best Things to Do in Boston in Winter

Take a hands-on cooking class at Selfup Boston.
Skate on Boston Common Frog Pond or Seaport ice rinks.
Shop and snack your way through Boston Public Market.
Warm up with live music in a North End café.
Catch a show at the Boston Opera House or Huntington Theatre.
Stroll the Seaport for winter lights and harbor views.

Day 1: Food, Markets & a Cozy Celebration

Morning – Explore Boston Public Market

Start your winter weekend at Boston Public Market, where local vendors sell everything from fresh donuts to New England cheeses. It’s indoors, lively, and a great way to support local makers while staying warm.

Afternoon – Stroll the North End

Boston’s Little Italy is magical in winter. Wander cobblestone streets, pop into cafes, and stop for hot espresso or a slice of Italian pastry.

Evening – Cooking Party at Selfup

Instead of another restaurant reservation, make your Saturday night unforgettable with a Selfup cooking class. Led by professional chefs in our downtown Boston kitchen, you’ll cook, laugh, and celebrate together. It’s one of the best indoor activities Boston has to offer - whether you’re planning a birthday, a bachelorette, a fun night out with friends, or even heading out solo to meet new people.

👉 Book a Boston cooking class or surprise someone with a gift card .

Day 2: Outdoor Fun & Cozy Escapes

Morning – Ice Skating on Frog Pond

No list of things to do in Boston in winter is complete without skating on the Boston Common Frog Pond. For harbor views, head to the Seaport ice rink.

Afternoon – Brewery Tours & Local Tastings

Warm up with a craft beer flight at Harpoon Brewery or explore smaller local taprooms like Trillium. If beer isn’t your style, check out hot chocolate tastings around the city.

Evening – Theatre & Nightlife

Wrap up your weekend with a show. Boston Opera House, Huntington Theatre, and smaller venues offer performances that range from Broadway hits to indie plays. Afterward, head to Seaport for rooftop lounges with heated patios and glowing winter lights.

Why Boston Winters Are Perfect for Experiences

Winter in Boston can be cold, but that’s what makes it special. The city offers:

Outdoor charm: skating, snow walks, harbor lights.
Indoor warmth: cooking classes, live music, theater.
Local flavor: markets, breweries, and hidden cafés.

Choosing experiences over reservations means your winter weekend becomes more than sightseeing - it becomes a story worth retelling.

The Best Indoor Activity in Boston

If you’re searching for winter activities near me or simply want a night that goes beyond dinner, Selfup Boston is the answer. A cooking class brings people together in a way that’s warm, interactive, and unforgettable. It’s also one of the top experience gift ideas in Boston for the holiday season.

👉 Ready to celebrate winter differently? Explore Selfup Boston classes today.