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Published November 2, 2023

Boston's Ultimate 2023 Winter Bucket List

Holiday markets, ice sculptures, and more—here’s how to get merry in Boston this winter! 🧣⛄🎄

by Boston Bucket List


From the cobblestone streets to the Boston Common pines to the horse-drawn carriages and beautiful snow, there’s nowhere in the world quite like Boston in the winter.

Whether you love cuddling up by the fire with a luscious cup of hot cocoa, whizzing around the ice skating rink hand-in-hand with friends, or shopping small businesses in a European-inspired market, there are endless ways to celebrate the season in Beantown. Luckily, we’ve gathered all of the best events and activities for you. Here’s Boston’s ultimate winter bucket list!

17 Things to Do in Boston This Winter & Holiday Season 

See the Lighting of Boston's Official Christmas Tree

Boston's official Christmas tree has a unique history—in December 1917, two ships collided in Halifax Harbour, causing a devastating explosion. Boston sent immediate aid to Nova Scotians, and as a thank you, the province has provided a beautiful Christmas tree to the city of Boston. The friendship between the two cities has been going strong now for over 100 years! This year's tree is set to arrive in City Hall Plaza on November 21 this year, with the lighting ceremony kicking off the day after Thanksgiving on November 24.

Where: 1 City Hall Square, Boston, MA
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Go Ice Skating on Frog Pond

There’s no Boston winter tradition as sacred as ice skating on the Boston Common. Bundle up, grab a cocoa, and coast through the crisp air under twinkling lights for a truly magical evening.

Where: 38 Beacon St, Boston, MA
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Watch Nutcracker! Magical Christmas Ballet

Everyone's favorite Christmas performance is back at the Boch Center Wang Theatre with Sugar Plum fairies, sword fights, snowy adventures, and more. Experience the extraordinary international cast and Ukrainian Principal Artists performing at the peak of classical European Ballet and be transported by the magic of jaw-dropping acrobatics, larger-than-life puppets, and stunning hand-crafted sets and costumes.
Where: Boch Center Wang Theatre: 270 Tremont Street, Boston, MA
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Boch Center - Wang Theatre, 270 Tremont Street, Boston, MA 02116, USA
Nutcracker! Magical Christmas Ballet @ Boch Center Wang Theatre
Starting at $32

Book now


Visit the Snowport Winter Village

The Snowport Village at the Seaport is a true North Pole in the heart of Boston. Visit their Holiday Market to shop merry wares from local crafters and businesses and pick up some delicious artisanal treats. You can also try your hand at curling and even pick up a holiday tree to bring home from the Tree Market!

Where: 65 Northern Ave, Boston, MA
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Check Out the SoWa Winter Festival

South End’s most famous market will be merrier than ever for the 8th annual SoWa Winter Festival, which takes place over 4 weekends from November 24 to December 18. Shop more than 100 local vendors and enjoy some incredible treats by the firepits in the garden under the magical twinkling lights.

Where: 550 Harrison Ave, Boston, MA
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Watch the Menorah Lighting at Boston Seaport

Hannukkah kicks off on December 7 this year and runs through December 15. Join the celebration at Boston Seaport on December 10 when the Chabad of Downtown Boston lights a nine-foot-tall Menorah, accompanied by music and performances!

Where: 60 Seaport Boulevard, Boston, MA
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Go Skiing at Blue Hills

Did you know you can ski on a real mountain just 20 minutes outside of the city? It only takes a short drive to feel like you’re a million miles away, coasting down a snowy, tree-lined hill.

Where: 4001 Washington St, Canton, MA
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Get Wild at ZooLights

Take an evening stroll through 26 acres of paths and see festive animals like black bears and reindeer at Stone Zoo’s annual ZooLights event. Visit the unique holiday light display from November 17 to January 7.

Where: 149 Pond St, Stoneham, MA
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Warm up with a Hot Cocoa at The Four Seasons

The chocolate pop-up at the Four Seasons in Back Bay would put Willy Wonka himself to shame. Take in the lobby’s magical winter makeover while enjoying a bonbon or cookie from the luxurious hot chocolate and coffee bar.

Where: 1 Dalton St, Boston, MA
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Dine Inside an Igloo at The Envoy

Get one of the most unique tables in the city at The Envoy’s Lookout Rooftop & Bar this winter. Cozy up in a heated igloo while taking in views of the seaport and a delicious cocktail.

Where: 70 Sleeper St, Boston, MA
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Take in the Sights at View Boston

View Boston is a 360° taste of the city, offering breathtaking views atop one of the tallest buildings in New England. A perfect activity for out-of-town holiday guests, you'll ascend to the top of the Prudential Tower’s 52nd floor for incredible indoor panoramic views of the city. Get an even better look at the spectacular city skyline from The Lookout elevated viewing platforms and use the Virtual Viewers to learn more about the City’s many landmarks and attractions.

Pro-Tip: Tickets make a great experience gift for anyone on your holiday gifting list!

Where: View Boston at Prudential Center: 800 Boylston Street Boston, MA
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800 Boylston Street Boston, MA 02199
View Boston: 360-degree Observation Deck
Starting at $21

Book now


Take a Day Trip to the New Hampshire Ice Castles

For one of the most unique winter activities in New England, make the two-hour drive from Boston to the ice castles in New Hampshire. From ice slides to caverns to snow tubing and the fairy forest, we promise you’ve never experienced anything quite like it.

Where: 24 Clark Farm Rd, North Woodstock, NH
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Shop the Bow Market

The Bow Market in Somerville is the perfect place to pick up quirky gifts and handmade goods ahead of the holidays. Shop small makers, artisans, bakers, and more at this storage building turned hipster shopping paradise. When you've had your fill of holiday shopping, unwind with a warm drink by the cozy firepits!

Where: 1 Bow Mkt Way, Somerville, MA
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Go Sledding

Looking to have some good old-fashioned winter fun in the city? Grab a tube and go sledding at one of Beantown’s infamous hilly parks, like the Common, Lars Anderson Park, Arnold Arboretum, or Jamaica Plain’s Sugar Bowl. Don't forget your hats and gloves!

Where: Arnold Arboretum, 125 Arborway, Boston, MA
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Volunteer or Donate to a Worthy Cause

Want that warm, fuzzy feeling of doing something good around the holidays? Take the opportunity to volunteer your time or money at one of Boston’s incredible charities, like the Greater Boston Food Bank, Cradles to Crayons, or the Animal Rescue League Boston.

Where: Various locations


Take an Ice Sculpture Stroll

Looking for something ~cool~ to do on New Year’s Eve? Take a walk and marvel at some of the seriously creative ice sculptures that will displayed on New year's Eve. Sculptures will be located in City Hall Plaza, at Boston Common, and along the waterfront. They will be available for public viewing from 12:00 noon to 12:30 AM. The best part? It’s completely free! 

Where: Boston Harbor between East Boston and Boston’s North End
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Spend New Year’s Eve at First Night Boston

There’s no better way to ring in the new year than to enjoy Boston’s biggest celebration of art and culture: First Night! The event features performances of singing, dancing, burlesque, acrobatics, comedy and more at various locations across the city, plus ice sculptures and a parade. All you need to enjoy it all is an all-access button. The event culminates with a spectacular fireworks show over the harbor at midnight.

Where: Various locations
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