Things to Do in Boston in Winter

What's the holiday season without a market? Held annually at the City Plaza Government Center, the Boston Winter Holiday Market is one of the most popular events in Boston, attracting close to 100,000 visitors each year. It opens the day before Thanksgiving and runs through New Year's Eve, offering visitors an ideal place to find the most unique holiday gifts.

Whether you're looking for holiday gifts or hoping to spend the day in a cozy, indoor spot, Prudential Center (called "The Pru" by locals) won't let you down. They've got all the big names, like Saks Fifth Avenue, Ann Taylor, Canada Goose, Lululemon, L'Occitane, and Sephora. You can even buy a Peloton bike or an armful of books from Barnes and Noble.

Only hardcore sailors would be willing to rip through the frigid waters of Boston Harbor between November and April. Apparently, there are a ton of people willing to do just that. If you're one of them, bundle up and head to the Boston Sailing Center in Lewis Warf or Winthrop Frostbite Sailing Club in Winthrop (near Boston's Logan airport).

Boston's main theater district consists of over a dozen venues set in the downtown core. Whether you're looking to attend a Broadway musical, Christmas-themed performance, or dance show, you'll find it all (and so much more) in this glitzy area.

Face it, there's no such thing as too much chocolate. That's why we had to add a tour of the Taza Chocolate Factory to our list of the best things to do in Boston in winter. You're welcome!

There's no better drink to warm your chilled bones than a sweet cup of hot chocolate. From sickly sweet to spicy to vegan, winter travelers will be rewarded with a wide variety of hot chocolate options to tickle their taste buds. Here are our favorite spots:

Good news for those looking for an inside activity. Boston is home to some of the country's oldest (and some would say best) museums. The Boston Tea Party Ships & Museum is unmissable, and easily one of the best places to visit in Boston in winter.

The most incredible view of Boston can be found at the Prudential Skywalk Observatory. The best time to visit is during the late afternoon, when you can watch the sunset alight the sky with pink and orange hues.

While a smattering of snow might make it hard to spot the 2.5-mile-long red-brick line marking the Freedom Trail in winter, it's still one of the best places to visit in Boston. This long, winding path passes 16 of the city's most important historic sites, including the Massachusetts State House, Old South Meeting House, Old State House, and the site of the Boston Massacre.

Unleash your inner Michelle Kwan (or perhaps just try to make it around a lap without falling) on the Boston Common Frog Pond. Set in the heart of the oldest public park in the country, this beloved pond is home to a skating school, and offers skate rentals, including seal-shaped aids to help little ones (or wobbly adults) find their balance.