Last updated December 2023 ■
Words by Georgie Ashworth
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As the annual winter chill settles in for the season over Boston, the city transforms into a wonderland of lights, festivities, and seasonal cheer. There is so much going on in the city and we have pulled together a of the top 10 things to do in Boston this winter. Snuggle up and settling into cozy Christmas meals, visit the Christmas markets in Boston and great resident events at The Bon. Boston has a lot to offer during this magical time of the year.
Boston foodies rejoice! The food scene really kicks off during the holiday season, there is a huge choice of Christmas meals to suit every budget and taste. We recommend iconic eateries No. 9 Park and L’Espalier (which happens to be just a few minutes from your new home in Fenway) for a high-end dining experience, complete with festive menus and a cozy setting. Both of these spots are perfect if you are looking to treat someone special (or yourself!) this wintertime. For a more casual winter meal, head over to neighborhood legends like The Bell in Hand Tavern (famously America’s oldest tavern) or Union Oyster House, where you can savor a traditional New England Christmas feast. Bon appetite.
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Boston's best dessert
Christmas feast in Boston
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Christmas feast in Boston
Who doesn’t enjoy a Christmas Market?! We will wait… Immerse yourself in the holiday spirit at the Boston Christmas Markets, a bustling hub of festive stalls, local artisans, and seasonal delights. Faneuil Hall is a fantastic place to visit at in Boston in Winter. Here you will find lots of outdoor stalls, you can find unique gifts, enjoy delicious seasonal treats, and revel in the festivities and good vibes while sipping a mulled apple cider. They host festive events, so make sure you keep an eye out for some events like carol singing and go and visit just to see one of the best Christmas trees in Boston! Generally the Christmas Market makes a great one-stop-shop for all your holiday shopping needs.
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Boston Christmas market
Boston Market
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Boston Market
Soak up the glittery city. The annual Boston Common Christmas Tree Lighting ceremony is a cherished tradition that kicks off the holiday season for Bostonians. Head to Boston Common to marvel at the massive Christmas tree – which is definitely one of the biggest in the city. Join locals and tourists alike to witness the majestic tree lighting up the night sky. Make sure you visit the Columbus Park Trellis with the 50,000 led light tunnel – making for epic photo opportunities. And you have to go and see Macy’s iconic Christmas window displays – just ‘cause!
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Boston Christmas lights
Boston Christmas lights on the wharf
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Boston Christmas lights on the wharf
Ranking a strong #31 on things to do in Boston in Winter on trip advisor, is a trip to Boston Common’s magical winter wonderland. This is a whimsical wonderland with activities to for all ages. Take a stroll through the park while marvelling at the twinkling lights, take a spin (and a tumble) around the ice skating rink, and warm up after with hot cocoa at the Frog Pond Café. This is a quintessential Bostonian experience that captures the magic of winter in the heart of the city.
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Boston Winter Wonderland
Snowman Boston Wonderland
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Snowman Boston Wonderland
The Freedom Trail is an iconic Bostonian experience at any time of the year. Why not wrap up warm this winter and embrace the chill with a guided tour along the trail. This is a great opportunity for you to explore the city's rich cultural and political history whilst also getting some steps in and whilst soaking up the neighborhood festivities. Bundle up and follow the red-brick path to iconic landmarks such as the Massachusetts State House and Paul Revere's House, all adorned with festive decorations during the holiday season.
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The freedom trail
Boston, old city hall
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Boston, old city hall
Escape the hustle and bustle of the city with a day trip to the Boston Harbor Islands. Head to Long Warf to jump onto a ferry, and enjoy the journey to Spectacle Island and or Georges Island. Once you arrive, enjoy serene winter landscapes, coastal walks, and panoramic views of the Boston skyline. This makes for a perfect day out in winter, we recommend you pack a picnic and a flask of hot cocoa, enjoy!
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Lookout from Boston Islands
Boston Islands daytrip
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Boston Islands daytrip
Take some time for yourself this winter and escape the chill by stepping into the grandeur and warmth of the Boston Public Library. They host regular book readings that you can attend, or simply just find a cozy nook to enjoy a good book. The library's is truly a serene retreat. This is the perfect way to while away some long wintery hours over the holiday season.
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Cozy afternoon reading
Winter afternoon in Boston Library
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Winter afternoon in Boston Library
Take some time this holiday season to visit and experience a unique blend of history and holiday cheer at the Boston Tea Party Ships & Museum. Join for the "Huzzah for the Holidays" event, where you can participate in interactive exhibits, enjoy festive reenactments, and even have a go at throwing tea into the harbor.
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Boston river at sunset
Winter in Boston
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Winter in Boston
City Hall Plaza transforms into a winter spectacle with the annual Boston Winter event. Why not explore the outdoor holiday market, take a spin around the ice on the custom-designed rink, and warm up with seasonal treats – don’t miss the hot mulled cider. Soak in the festive atmosphere, holiday decorations and entertainment. This is a winter lovers heaven
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Boston in winter
The Boston Christmas tree
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The Boston Christmas tree
The Bon residents rejoice! If you don’t fancy going out and about this winter, then staying in and keeping cozy can be just as great. We have a range of resident activities from joining our gift-wrapping station, to card making through to festive drinks. You could also book out the dining room to host some friends for a festive dinner or gather some friends for a Christmas movie in the movie theatre too. Or just snuggle up in your apartment and hibernate for the season! The choice is yours.
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The Bon - views over the city
The Bon, resident chilling
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The Bon, resident chilling
Boston, has a rich history and vibrant community with varied things to do across the city and throughout the festive season to make your winter truly special. Whether you're indulging in a festive Christmas meal, exploring the holiday markets, or enjoying some R&R, Boston has something for everyone. We hope this guide gives you some ideas how to spend your holiday time in the City.
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