New England is certainly known for its many historic small towns, which are charming no matter the time of year. If you’re looking to explore Bay State towns this winter, here are some of the best small towns in Massachusetts to snuggle up in.

1. Northampton

Northampton, MA, USA
David-Michael Cook/Flickr
Home to Smith College and surrounded by forests and the Berkshires, Northampton is an idyllic town that turns into a wonderland in the winter. While you're in town, make plans to visit the local art museum, stroll the downtown, and have a drink at Tunnel Bar, a cozy underground spot with an excellent selection of cocktails. This is truly one of the best small towns in MA.

2. Lexington

Lexington, MA, USA
John Phelan/Wikimedia Commons
Step into the Colonial era with a visit to historic Lexington, a town that's known best for its role during the American Revolutionary War. Historic towns always have cozy spots for snuggling, so, after exploring the numerous historic attractions within this lovely small town in MA, retire to one of the many inns in town like the luxurious Inn at Hastings Park, which provides the perfect accommodations for snuggling. And do not miss checking out Battle Road Trail.

3. Sandwich

Sandwich, MA, USA
DenisTangneyJr/ E+ via Getty Images
While we may think of the town of Sandwich strictly as a summer destination due to its location on the Cape, it's also quite an enchanting place in the winter. It is also much quieter during the cold months, making it a wonderful time to explore without the crowds. If the weather permits, you can stroll along the Sandwich Boardwalk, visit the Sandwich Glass Museum, visit the Heritage Museum and Gardens, shop for antiques, and more. Another one of the best small towns in Massachusetts, it is also filled with historic inns that will make you feel right at home.

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4. Rockport

Rockport, MA, USA
Thomas H. Mitchell / 500px via Getty Images
Winter is the time to come to Rockport if you want to escape the hustle and bustle of the normal tourist crowds. Experience the peace and quiet during the colder months as you stroll around Bearskin Neck and visit the numerous shops and galleries. Head to the harbor for an unspoiled photo of Motif #1, visit a museum, and grab a bite to eat at one of the many restaurants. You may find that winter is the most wonderful time of year to visit one of the coziest towns in Massachusetts. Get to know more about Rockport.

5. Lenox

Lenox, MA, USA
Massachusetts Office Of Travel & Tourism/Flickr
Whether you visit Lenox for a restful wellness retreat at Canyon Ranch, explore the snowy great outdoors, go shopping, or even spend some time at the local bookstore with a wine bar, you'll love how cozy it feels during winter in this lovely small town in MA.

6. Oak Bluffs, Martha's Vineyard

Oak Bluffs, Martha's Vineyard, MA, Oak Bluffs, MA 02557, USA
Massachusetts Office Of Travel & Tourism/Flickr
While you may think of Martha's Vineyard as a summer destination, it's actually quite a cozy place to be come winter. Book a stay at an inn with a homey feel, perhaps the Tivoli Inn which is set in a gingerbread house. Speaking of gingerbread houses, you must take a magical stroll through the Oak Bluffs neighborhood that has 300 of these whimsical structures. Oak Bluffs also has numerous restaurants and shops you can walk to, although some may be closed for the season. Learn more about Oak Bluffs.

7. Deerfield

Deerfield, MA, USA
Massachusetts Office Of Travel & Tourism/Flickr
Deerfield was settled in the 17th century during the colonial era. Over time, it has maintained its small-town feel and offers a restful place with a slower pace of life that's perfect for a getaway. It's also home to Yankee Candle Village, Richardson's Candy Kitchen, an antique shop, a country store, and so much more! Stop by for a meal of delicious comfort food at the incredibly cozy Champney's Restaurant located at the exquisite Deerfield Inn.

Wouldn’t you love to visit the best small towns in MA this winter? Tell us which town is your favorite in the comments!

Don’t forget to book a place to stay in some of the coziest small towns in Massachusetts! Check out what VRBO has to offer!

Looking for things to do while you’re here? Check out these winter activities in Massachusetts.

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More to Explore

Winter In Massachusetts

Rachel Raimondi | February 02, 2024

Where should I go hiking in winter in Massachusetts?

While you are out visiting some of the best small towns in Massachusetts, be sure to stop for some winter hiking in Massachusetts:

Appleton Farms: Located in Ipswich, here, you can take in six miles of farm roads and paths throughout an actual working farm. Bring your snowshoes and stop to visit some of the animals that live here before you leave!

Stavros Reservation: If you are like me and sometimes only have time to get a quick walk in, this spot in Essex is for you! Here, you’ll find a three-quarter-mile trail that features gorgeous beach views and even some salt marshes.

Where can I go skiing in Massachusetts?

Another really fun thing to do while you are touring small towns in MA? Check out places to ski in Massachusetts:

Wachusett Mountain: Located in Princeton, here, you have 27 trails to choose from with three chairlifts to get you around. There are also two terrain parks, ski classes, and an assortment of places to grab a bite at the base lodge.

Ski Ward Ski Area: This ski area in Shrewsbury has five lifts for nine trails. You’ll also find 12 tubing lanes and a terrain garden and learning pipe.

What are the best ice skating rinks in Massachusetts?

Lace and bundle up and get out to some of the best ice skating rinks in Massachusetts:

Skate at Canal District Kendall: You’ll find this rink located in Cambridge. It is open from about December through March and offers skate rentals and lessons.

The Rink at Market Street: Head to Lynnfield for this rink conveniently located within the shopping complex. If you get too chilly, there is a warming tent and fireplaces to gather around.

 

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