Sharing is caring!

Searching for a Boston Winter Guide because you are debating visiting Boston in the winter? Yes? Well then, read on because this post includes the best things to do in Boston during the winter time, for the perfect winter vacation in New England.


Boston is a destination on many peoples’ bucket lists, but is generally one that people tend to think of for the warmer seasons. But let me tell you that Boston is a great choice for a Winter Vacation in New England. Although the winter in Boston is cold, the city is very lively anyways and there are plenty of things to do in Boston no matter the season. Plus, it is just a fun spot for visitors and residents alike. There is also an excellent public transport system that is efficient even in bad weather and the new citywide plan, Imagine Boston 2030, will make it even better. According to the City of Boston website, Imagine Boston 2030 “prioritizes inclusionary growth and puts forth a comprehensive vision to boost the quality of life, equity and resilience in every neighborhood across the city.”

Boston Winter Guide - Best Things to do in Boston in the winter

So between your exploring of the cobblestoned streets, historic streets and charming neighborhoods across the city, you can catch public transport to your next destination should you find it to be just a bit too chilly to explore on foot. Ready for your Boston winter vacation?


Top things to do in Boston during Winter – Boston attractions Winter Edition

Here are a few of the best things to do in Boston and nearby areas during this time of wonderful time of the year.

Take a Boston winter tour

While it is too cold for the standard summer tours such as walking tours and Duck tours, there are plenty of winter tours that you can go on to still get a good feel for the city! For example, you can go on a trolley tour such as the Hop on Hop Off Trolley Sightseeing Tour, Boston Harbor Holiday cruise or brewery tour such as the Boston Brewery Tour or Historic Pub Crawl Tours. Just remember to bundle up!

Enjoy winter sports

The winter season is a busy sports season, and you can get inside at TD Garden for a hockey or basketball game. The Boston Bruins (for hockey) and the Boston Celtics (for basketball) are the home teams here and they come with quite the loyal and energetic crowds that will surely add to a memorable experience. Luckily, the winter season is when there are a lot of home games in Boston so you can probably catch a game or two if you are visiting Boston even for a short period of time.

Visit a museum

Boston is a historic city that is home to a number of incredible museums, and for the days when it is just too cold outside to be comfortable during the winter season, a few indoor activity ideas are a must! The Museum of Fine Arts, Museum of Science and Boston Children’s Museum are all great museums to visit in general, and they are also each close to transport stations so you don’t have to spend too much time outside in the cold. You can catch the Festival of Lights at the Museum of Fine Arts for Hanukkah, and join in for festive seasonal activities at the Boston Children’s Museum ‘Snowmazing’ event during December.


During the holidays, go see the tree at Fanueil Hall

Fanueil Hall is a historic spot in Boston that has been a hub for democracy and nowadays is a retail space that is home to a number of vendors for food, fashion, and other goods. During the holiday season, there is the Christmas tree that goes up in

Go ice skating on Boston Common’s Frog Pond

While there are a couple of spots in Boston to go ice-skating inside during the winter season such as the Warrior Ice Arena, there is nothing like ice-skating outside during the winter season. Frog Pond is the most popular outdoor ice-skating rink in Boston. Located within Boston Common, Boston’s central park, you can join in on the fun here with your own skates or rent a pair, and stop for a hot cup of something at the nearby café.


Have a treat at one of many Irish Pubs and historic taverns

Many of the Irish Pubs and historic taverns in Boston have been around since the American Revolution. They make for the perfect spot to pop into for a tasty treat and/or brew, listen to music, and experience the ‘real’ Boston.  

Visit Sam Adam’s Brewery

The Sam Adams Boston Brewery offers free weekday tours that last 45 minutes and are available year-round. First come, first serve for tours! 


Take a walk in the Arboretum

Although Boston is a proper charming city, sometimes you just want to see the open spaces, feel the snow beneath your feet and breath in the (albeit cold) fresh air. The Arnold Arboretum a tree sanctuary that is open year-round and is a beautiful spot for a winter stroll.

Climb the Bunker Hill Monument

Bunker Hill was the site of the first major battle during the American Revolution. The Bunker Hill Monument was constructed in 184, with 294 steps and panoramic views from the top, to commemorate the battle and lost soldiers. Admission is free, and it is a great spot to both pay mind to and experience the historic part of Boston and catch some gorgeous views of the city.

bunker hill monument boston

Boston nearby areas to visit during Winter

In Salem, MA go see the Christmas tree in Salem House Tour

Salem, Massachusetts is another historic city and it hosts the Salem House Tour for a few days from the end of November to the beginning of December. The Salem House Tour consists of decked out incredible homes that you can check out to appreciate both the architecture of the homes as well as the festive spirit.

Note: You can always book historic walking tours and also haunted night tours.


In Somerville, MA take a Christmas lights tour

Somerville, Massachusetts is a magical spot to visit for a Christmas Lights tour. Somerville hosts a 45-minute tour called the Illuminations Tour, which you can join via trolley or do a self-guided tour to the festive spots.


Friendly reminder: With so much to see and do during the winter season in Boston, remember to pack a warm coat or two, snow and cold weather clothes, and proper boots for the snow! You don’t want your wardrobe to limit you on all that there is to do.

Have you been to Boston during the winter? If so, what do you recommend doing there during this time of year?

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.


Let’s keep in touch

Join other travelers and get the latest travel updates, travel tips, tricks and insider secrets. Be notified first about giveaways and special events.

Scroll to Top