10 Things to Do in Boston in the Winter

Boston in the winter can be a magical time, with the city covered in snow and a festive atmosphere in the air. Despite the chilly weather, there are still plenty of things to do and see in this historic city. While you may be inclined to stay indoors and read a book, try heading outside to experience the best the Boston area has to offer. From ice skating and sledding to nature hikes and tasty bites, there are options for everyone. 

Whether you’re looking to rent an apartment in Dorchester or find a new home in Hyde Square, here are ten ideas to help you make the most out of winter in Boston. 

1. Take a tour of Fenway Park

Start your day off by visiting one of the most iconic sports venues in the country. Home of the Boston Red Sox, Fenway Park is open for tours all year round. Take a walk around the historic stadium, learn about its history, and see the view from the Green Monster. 

If you tour during the baseball off season, you may be able to run the bases and visit the dugouts. Tours range in price and length from $15 for a 15-minute tour to $25 for a 60-minute tour. 

2. Visit the Museum of Fine Arts

When you’ve had your fill of baseball, head over to the famous Museum of Fine Arts. The museum is open year-round and has an extensive collection of art from around the world, including works by Monet, Van Gogh, and Vermeer. 

3. Try your hand at winter sports

Just because it’s winter doesn’t mean you have to hibernate. Luckily, Boston has plenty of spots for outdoor winter activities. 

“If you’re looking for some winter exercise, practice your balance and lower body engagement by ice skating at Frog Pond,” suggests Alex Cruz, Certified Physical Therapist and Director of Education for CLIENTEL3. “If you’d rather let gravity do the work, go sledding around the corner or on any local hill,” she continues. “And after all that exercise, treat yourself to local business delights at The Holiday Market at Snowport. There are options for everyone, ranging from freshly baked cookies to full meals from expert chefs.”

4. Visit Faneuil Hall Marketplace for historic eats

If athletics aren’t your thing, head to the historic Faneuil Hall Marketplace to enjoy the year-round crowds and lively food court. Commonly called Quincy Market, Faneuil Hall is made up of four markets surrounding a giant promenade. “You’ll be sure to find plenty of local vendors, artisan shopping, and unique restaurants and pubs,” notes Cassandra Chichester from Travel Agent Diary. 

5. Get your foodie on at local hotspots

It can be hard to make it outdoors on the coldest days in January. However, these can be the best times to head out for a satisfying bite without the crowds. 

“Bundle up in as many layers as possible and start your day with a coffee and pastry at Tatte in Beacon Hill,” says Tara West, owner of Tara West Fashion. “Then, stroll down Newbury Street and pick up some cool kicks at Concepts,” Tara continues. “Finally, work up an appetite as you walk to the North End for a delicious plate of pasta and a fabulous glass of red wine at Lucca. Don’t forget to finish your day by grabbing a cannoli and a piece of chocolate cake at Mike’s Pastry.”

6. Stroll over to Bow Market for a unique experience

For those looking for a secluded hotspot, consider visiting Bow Market in Union Square. “Many locals don’t even know about it,” state Dante Bellucci and Carol Perris, owners of Vinotta Italian Restaurant. “The market is a hip spot with small shops, eateries, and more. 

If you want to work up an appetite beforehand, visit Robbins Farm Park for some legendary sledding. “It’s just a short drive from downtown Boston and has gorgeous views of the skyline in the distance,” continue Dante and Carol.

7. Catch the sights along the Charles River

Day or night, strolling along the Charles River offers something for everyone. “Soak in the sights of MIT and the Boston Commons,” recommends Anastasia Aranovich, a photographer based in Boston. “The views shift between Boston Brownstones and the open river as you make your way along the river,” she says. “If you’re lucky, you can watch sailboats floating across the water. When you’re done, head up to Newbury Street to get a warming cup of tea and some pastries.”

At night, you can watch the holiday lights twinkle over the water.

8. Take advantage of the early sunsets 

No need to stay up late to witness the city at night; the sun sets at around 5 pm from December through February. 

“After a long day out, head to the Four Seasons to warm up and drink a cup of afternoon tea,” suggests Melinda Davala Sarkis, a Boston real estate agent. “As the sun sets, head across the street and stroll through the Public Garden to take in all the Holiday lights,” she continues. “Finish the day with an evening of great food at Contessa while watching the snow fall over the city.” 

9. Visit the White Mountains for a wintry escape

Get the most out of a Boston winter by taking a weekend road trip to the White Mountains. “Grab some friends and family and head north to spend a snowy, magical weekend in a cozy log cabin,” recommends Cam Chesley from CS Luxury Group. “You can experience breathtaking mountain views while skiing, snowboarding, tubing, or hiking,” he says. “If you prefer to stay local, hop over to the North End and check out Panza on Hanover Street for dinner. When you’re finished, don’t forget to swing by Bova’s Bakery around the corner to try their famous cannoli for dessert.”

10. Head up to Middleton for a change of scenery

If you’ve made your way around the city and are looking for somewhere new to explore, consider heading north to Middleton. “Visit Middleton for top-notch ice cream, hiking, sledding, and food,” says Real Estate Advisor Victoria Dimino. “Located just 20 miles north of Boston, there are ample activities for a winter adventurer in this small city,” she says. “On any snowy day, you’ll find plenty of people sledding down local hills and trekking up nearby trails. After some outdoor adventures, hit up nearby Maggie’s Farm for some tasty treats and live music.”

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