23 Ideas for a Wonderful Winter in Boston

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Some of the most iconic photographs of Boston feature autumnal scenes, but visitors should also know that winter in Boston is pure magic. From cozy indoor activities to electrifying outdoor adventures, opportunities for exploration and fun abound! Read on for ideas you won’t want to miss on your next winter visit to Boston!

Admire the Cityscape aglow in Lights

One of the most spectacular ways to experience Boston in the winter is outdoors. It may be chilly, but step outside to admire the lights all around, and you will be entranced. 

Stroll through Downtown and the Back Bay

All through winter, much of downtown Boston is twinkling. Lights adorn trees, lamp posts, and buildings, making evening walks even more inviting. Take a stroll on the Boston Common, where trees are lit up in a host of different colors. Cross over into the Public Garden, where the illuminated bridge and trees are absolutely romantic. Walking along the Commonwealth Avenue Mall, adjacent to the Public Garden, you’ll be surrounded by sparkling lights that will inspire a sense of magic and wonder in you. 

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Ice Skating 

In the winter, is there a better way to spend time outside than ice skate? With numerous public, low-entry fee outdoor ice rinks, there are ample opportunities to admire the city on skates, whether you can nail a double-axel or you’re holding the sides of the rink closely. The Frog Pond on Boston Common offers daily skating with views of the Massachusetts State House and brick-lined Beacon Hill.

Snowport, a winter village featuring an ice rink in the Seaport neighborhood, is a trendy spot to shred some ice. Visitors can even reserve a curling lane! If you’re in Cambridge (directly across the Charles River from Boston), try out the under-the-radar Skate @ Canal District Kendall, where you’ll be gliding across ice in the city’s innovation district. No need to pack skates for your trip – rentals are available at all of these locations.

ZooLights at the Stone Zoo

If you’re an animal lover, you won’t want to miss ZooLights at the Stone Zoo in Stoneham, a northern suburb of Boston. An evening trip is doubly delightful! Not only will you get to see the animals that make this space spectacular (some highlights are lions, flamingos, and Arctic foxes), but the lights will put you in festive spirits. If you don’t have access to a car but want to immerse yourself in the world of animals, visit the Franklin Park Zoo, located in Boston.

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Keep cozy on a Hot Chocolate Crawl!

It’s no secret that it can get pretty cold during the winter in Boston. Averages temperatures in January through March range from the 20s to the 40s (Fahrenheit), though it can get even colder. So put your puffy coat on and get ready to check out some (or maybe all of) Boston’s best hot chocolate havens! 

Thinking Cup (Back Bay, Downtown, North End)

A Boston staple, Thinking Cup serves delectable French hot chocolate. This liquid chocolate is so richland creamy that you’ll want to savor every sip slowly in Thinking Cup’s cozy digs. With three locations – Back Bay, Downtown, and the North End – you have no excuse not to stop by and have sip!

Max Brenner (Back Bay)

One of only three U.S. locations, this “chocolate by the bald man” shouldn’t be passed up! The Back Bay institution serves a huge menu of hot chocolates, from Original to Mexican Spicy to Salted Caramel. Don’t be surprised if you leave with a box of treats to go too.

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Cacao, Jamaica Plain

This neighborhood favorite is steeped in positivity and intoxicatingly good scents. Their Dulche de Leche hot chocolate is creamy and dreamy on a chilly day! If, like many Bostonians, you enjoy an icy treat even on the frostiest of days, try the iced mocha. 

LA Burdick Handmade Chocolates, Downtown Boston and  Harvard Square

This stylish yet down-to-earth spot has carefully crafted speciality hot chocolates across the taste spectrum. Your palette will be pleased with any of the artisanal goods you encounter here!

Gates Commes des Filles, Somerville

This authentic French chocolate shop (it’s name translates to “spoiled like girls”) is located in Somerville’s hip Bow Market. The signature hot chocolate is crafted with incomparable homemade whipped cream. With an owner who studied at the Cordon Bleu in Paris, you know the drinks will be tres bien!

Brothers & Sisters, Brookline Village

An amazing array of seasonal lattes and other hot beverages (try the mulled cider or honey pumpkin latte!) await you at this local gem! Located immediately west of Boston, Brothers & Sisters Coffeehouse and Cafe is a community-driven small business with endless charm. Other great coffee shops in Boston can be found on this list.

Consume Boston’s Rich History & Culture

From the cozy comfort of a museum or the refreshing briskness of the Freedom Trail, there’s tons to see and learn in Boston. Beantown has a rich history that draws visitors year-round, but one more perk of visiting in the winter is that there are far fewer visitors,, so you won’t likely face crowds or wait times. 

Walk the Freedom Trail

Covering 2.5 miles of terrain and marked in inlaid bricks, the Freedom Trail is a walking path connecting 16 sites of historic importance in Boston. Beginning at the Boston Common downtown and winding all the way to the Bunker Hill Monument in Charlestown, you’ll enjoy it whether you’re a complete history buff or fun facts are more your thing. Stop in at a visitor center at Boston National Historical Park at Faneuil Hall or the Charlestown Navy Yard for programs on the 17th-19th centuries and information about the area.

Also near the start of the Freedom Trail is the Boston African American National Historic site, where you can learn about the abolitionists of Beacon Hill and the ways people of color shaped Boston.

Old Town Trolley Tours

If you want to see everything without trekking around town, winter bus tours are an excellent option. Old Town Trolley operates 90-minute guided tours most Thursdays through Sundays in the winter months. Visitors will see and learn the significance of Boston’s most famous sites all from the comfort of an enclosed trolley.

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Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum, situated in the Fenway neighborhood, offers an unparalleled museum experience. The lush courtyard is a popular photo spot that will instantly transport you to the world of the museum’s eponymous founder. Take a tour with a docent or explore on your own and be swept away by the worldly collections and the uniquely designed rooms.

Boston Public Library 

Book lovers and design aficionados will swoon over the beauty of the Boston Public Library in Copley Square. Art and Architecture Tours, led daily, are an excellent break from the chill outside and offer a chance to learn about an institution central to Boston’s past and present. From the enchanting Bates Hall reading room to the iconic lions outside the entrance to the courtyard at its heart (not to mention the  thousands upon thousands of books), you will be enchanted by the Boston Public Library.

The Museum of Science 

With 130,000 square feet of exhibit and gallery space, the Museum of Science offers hours of entertainment for visitors of all ages. Among its permanent exhibits are real dinosaur fossils, New England habitats, an interactive Hall of Human Life, and Nanotechnology. Plus, new exhibits rotate through several times a year,, so there’s always something exciting happening.

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Get a Taste of Boston’s Contemporary Curiosities

Amongst Boston’s modern-day treasures, there’s something for everyone. From shows to shopping, and from chocolate to crafts, make sure you carve out time to partake in the city’s contemporary offerings. 

Taza Chocolate Factory, Somerville

Take a tour of the Taza Chocolate Factory – no golden ticket required! You will satiate your sweet tooth and learn something new at this Somerville spot. On a tour, you’ll learn about the chocolate-making process and have the possibility of seeing it get made. And yes, there are samples, complete with chocolate guides who will  let you know what you’re tasting!

Coolidge Corner Theatre, Brookline

A local favorite, the Coolidge Corner Theatre has been around for nearly 100 years. Today, this nonprofit cinema features everything from cult cinema to big screen classics. Its art deco appearance and community-driven spirit make it a true treasure. It’s the perfect place to go for an evening activity or a rainy day. 

Roxy’s Grilled Cheese, Central Square

Roxy’s Grilled Cheese sandwiches are melt-in-your mouth amazing. These delectable melts contain so much more than cheese and bread. Try “The Allston” for a savory sweet treat or the “Green Muenster Melt” for a smoky bacon-filled dream dinner. Don’t just grab some tasty grub though. Head into the back room and you’ll step into the A4cade, an arcade and bar complete with everything from PacMan to pinball.

The Garment District, Kendall Square

For the funkiest finds around, head to this “alternative department store.” Part costume shop, part thrift shop, and part new clothing store, this place is a whole lot of fun. No matter your style, you can spend hours trying clothes and costumes on at this fun Cambridge shop.

SoWa Open Market

Every Sunday, Bostonians and visitors flock to the South End neighborhood to visit the SoWa Open Market. Here, you’ll encounter an engaging shopping experience, featuring local artists, plus food and beverage vendors. Whether you’re looking for holiday gifts or for a treat for yourself, shopping at SoWa supports local artists and has countless unique treasures. 

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Catch views of the skyline in wintry wonder

No matter where you are in Boston, you’ll get amazing views from the vantage point of a rooftop. Restaurants, bars, and other venues offer indoor and outdoor spaces where you can admire the city in its winter finest! While shorter days can sometimes be a bummer, your spirits will be lifted when you catch the sunset and all the angles of “the Hub” from one of these spots.

Lookout Rooftop & Outlook Kitchen at the Envoy Hotel

Views and cocktails from Lookout Rooftop are superb. Pair the panoramic views of Boston Harbor from the indoor lounge or outdoor heated igloos with one of the unique craft cocktails, and the only chill thing will be the vibe!

Dorchester Brewing Company 

On an industrial stretch of road in Boston’s biggest neighborhood, Dorchester Brewing Company is unassuming at first. But take a look up and you’ll notice its expansive roof deck and greenhouse-style rooftop beer hall, dubbed the “Hopservatory.” Order a house- or locally-brewed beer, wine, and cider on tap and admire skyline views of Boston from the south. Also featured on the main level of DBCo are a game room and a barbecue joint, where you’ll find a menu that meets most dietary needs and desires.

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Situated on the outskirts of Harvard Square in Cambridge, Daedalus will delight your senses all around. Although the rooftop is just one story above ground, the backdrop of Harvard’s stately campus combined with gentle lighting and intentional greenery will lift your spirits into a mellow ambiance. The casual restaurant features interesting New American cuisine plus a bar on each level. It also has heated dining pods bestowed with twinkling lights, so no matter the weather, you’ll be comfortable. 

Coit Observatory at Boston University

Okay, so you’ll be looking a *bit* above the skyline when you visit the Coit Observatory – up at the stars, to be specific. This observatory at Boston University hosts Public Open Nights every Wednesday evening from 7:30 – 8:30 in the winter. Depending upon the night and the weather, you’ll have a chance to learn about and view stars, constellations, planets, the moon, and astronomical occurrences, and take a look at them through a telescope. Tickets are free but must be reserved in advance.

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