Best Things To Do in Boston on a January Vacation this Winter

Are you planning a trip to Boston in January? Are you looking for a Boston vacation in January? Year-round, Massachusetts is a great vacation spot for domestic and international tourists alike. Countless of us will move away from the Boston area each year only to miss the seasons, and boy does Boston have seasons of fun! The Winter really gets started in late January, as sometimes we've been known to enjoy a 55+ degree day in December or January and a winter without much snow.

Here are some ideas on how to enjoy a Boston Vacation in January:



Ice Skating, Skiing, or Snowshoeing

In the city known for its Boston Marathon every April, we don’t slow down in the Winter. In fact, a little snow never stopped us, and most of us are equipped with a waterproof coat as well as snow tires or at least 4WD. So grab your gloves and get out there, feel the chilly winter air on your cheeks, and smile — it’s January in Boston!

  • De Cordova Sculpture Park Snowshoe Tours – a can’t miss activity for outdoor and art lovers!
  • Blue Hills Boston – a great beginner slope, just outside of Boston enjoy this “smaller” hill – they have lessons available and make their own snow!
  • Weston Ski Track – we’ve been going here since we were little, for cross-country skiing with a few “golf course sized” hills and a ton of fun to get your energy out by snow shoeing — the world is your oyster!
  • Great Brook Ski Touring – another awesome place to go cross-country skiing or snowshoeing, there’s some delicious eats and history in nearby Concord, MA
  • Wachusett Mountain Night Skiing – for the more adventurous downhill skiier, Wachusett is our tallest mountain in Massachusetts, and we have a blast night skiing here



Take a Food Tour or Chocolate Tour with Off The Beaten Path Food Tours


We run our Food Tours and Chocolate Tours year-round for a reason: they’re fun, life goes on in the winter, and our friendly guides are excited to meet you. Our Harvard Square Chocolate Tour is currently running, and Harvard Square is so romantic in the snow! So check the Tour Calendar for something fun going on this week. We’ll bring the smiles and the handwarmers!



World-Class Sports Games: Celtics or Bruins are going strong


Honestly, it’s just as fun watching in a sports bar in Boston as being at the game itself, and our College Sports Teams are equally impressive, especially local college hockey!



Visit Our Indoor Markets


We love our indoor markets here in Boston, some things never change. On our Union Square Somerville Food Tour we visit the Bow Market which features Etsy-makers and local small businesses. Venture a little farther north and check out Lowell’s Mill No 5 market inside a converted textile mill. In Cambridge, we have an Antique Market which is five floors of antiques and interesting finds.

Best Things To Do in Boston on a January Vacation this Winter

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Best Things To Do in Boston on a January Vacation this Winter



Snow Tubing and Ice Cream!


Venture a little farther north, across the border into NH and you’ll be able to enjoy a wonderful afternoon Snow Tubing in Nashoba Valley! Here in New England we love our ice cream year round, so you can try some Bedford Farms Ice Cream right afterwards. Or head back into the city for some hot chocolate.



Stay Warm with our Craft Breweries


Check out our blog post about our favorite craft breweries in Boston. There’s so much creativity in the Boston brew scene, from the label to the process/recipes to the names of the local bottles, these are truly labors of love. On our tours we often sample beer, and you can email us for specific recommendations if you want more recommendations.



Magical Outdoor Shopping


Cobblestone streets are made for the winter! So kick off your stilettos, put on a pair of UGGs, and join us for some outdoor shopping around the city’s oldest areas. Our favorite places to wander the cobblestones include: Harvard Square, Beacon Hill, and Newbury Street.



Indoor Sports: Golf or Rock Climbing, anyone?


Interval training? Keeping up that golf swing? There’s plenty of ways to enjoy yourself this Winter with indoor sports, all around the city. From trampoline parks to indoor golf to our favorite rock climbing gym, you’ll find something to suit your fancy!



Harvard Square January Chocolate Festival


Our Harvard Square Chocolate Tour was inspired by Harvard Square’s Annual Chocolate Festival. We are proud members of the Harvard Square Business Association. Come try out the festival for some free chocolate that serves hundreds, or purchase a ticket to a Harvard Square Chocolate Tour!



Enjoy Music


There are so many awesome music venues in Boston, and guess what — the weather won’t stop the tunes! Check out our list of our favorite music venues in Boston.



The Usual: Museums, Art Galleries, Restaurants, Historical Sites are all open


Check out some of our other recs of things to do in Boston like this blog post on Off The Beaten Path Things To Do in Boston. Like we said, we’re hearty New Englanders, and the show doesn’t stop just because of a little snowflake from the sky. You’ll be in good company, grab your Boston Tea and get out there, enjoy our city and explore all of its off the beaten path finds.

Our Food Tours and Chocolate Tours of interesting Boston neighborhoods are a can’t-miss Winter activity in Boston. So whether you’re a local or tourist, start practicing saying “wicked cold” and check our Tour Calendar for what’s going on this week.


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