There’s no doubt that New England winters can be dreary and cold, tempting us to stay inside all season. However, if you resist the urge to stay in and hibernate, you’ll find that some of our small historic towns are absolutely delightful this time of year. Bundle up and spend a day or a weekend exploring one of these charming gems. In our opinion, these are the very best small towns in Massachusetts to visit when the temperatures drop. So bundle up and enjoy your adventures!
- Northampton
cogito ergo imago / Flickr Feel like a cozy winter getaway? Look no further than Northampton, which is arguably the best winter town in the state. Visit the 19th-century Lyman Conservatory’s Palm House, browse Raven Used Books, and feast on Rooster Rolls at The Roost. No matter how long your stay, you’ll quickly fall in love with this charming New England town. Northampton, MA, USA
- Stockbridge
Doug Kerr / Flickr Stockbridge will steal your heart in any season. It’s so charming that Norman Rockwell himself used it as a model. In fact, the Norman Rockwell Museum is a top attraction! When it comes to unique day trip destinations in Massachusetts, Stockbridge is an excellent choice. Stockbridge, MA, USA
- Rockport
Amy Meredith / Flickr Rockport is a sleepy little seaside town in the winter, but that doesn’t mean you should skip it. This little artsy town is big on food, shops, and bookstores, not to mention the Tuck Inn, which is the perfect place to rest after a day of exploring. There’s so much to love about the town of Rockport, Massachusetts; in fact, you may just decide to relocate! Rockport, MA, USA
- North Adams
Doug Kerr / Flickr Next up on our list of some of the best small towns in Massachusetts to visit in winter is North Adams. From invigorating spring hikes to stunning fall foliage, North Adams has all kinds of seasonal appeal. But our state’s smallest city has a lot going on in the winter, too — come see for yourself. North Adams, MA 01247, USA
- Wellfleet
kirbyfest / Flickr Wellfleet was first settled in the 1650s, so it’s brimming with local history. This is an ideal destination for foodies — the seafood here is absolutely delightful. It’s one of our favorite small towns in Massachusetts for a quick weekend adventure. Wellfleet, MA, USA
- Deerfield
Doug Kerr / Flickr Speaking of spots that look like a Norman Rockwell painting, Deerfield is a great place to go when you need to get away from it all. Bundle up and take a picturesque walk down Main Street, which simply radiates old-fashioned charm. The historic district is actually considered to be an outdoor museum populated by 18th-century homes. Deerfield might just be one of the best-kept secrets in New England. Deerfield, MA, USA
- Berkshires
Doug Kerr / Flickr The former home of (you guessed it) Norman Rockwell makes a fantastic winter getaway. Take a tour of Arrowhead farm, Herman Melville’s former home, or Wheatleigh, a regal 19th-century mansion. At night, sip mulled cider by the fire at the Lion’s Den Pub. This picture-perfect destination in Massachusetts is one you won’t want to leave! The Berkshires, United States
Don’t be afraid to hit the road this winter and discover a few hidden gems in your own backyard. Do you agree that these are some of the best small towns in Massachusetts to visit during the cold months? Which places would you add to the list? Feel free to share your thoughts with us in the comments below — we would love to hear from you!
cogito ergo imago / Flickr
Feel like a cozy winter getaway? Look no further than Northampton, which is arguably the best winter town in the state. Visit the 19th-century Lyman Conservatory’s Palm House, browse Raven Used Books, and feast on Rooster Rolls at The Roost. No matter how long your stay, you’ll quickly fall in love with this charming New England town.
Northampton, MA, USA
Doug Kerr / Flickr
Stockbridge will steal your heart in any season. It’s so charming that Norman Rockwell himself used it as a model. In fact, the Norman Rockwell Museum is a top attraction! When it comes to unique day trip destinations in Massachusetts, Stockbridge is an excellent choice.
Stockbridge, MA, USA
Amy Meredith / Flickr
Rockport is a sleepy little seaside town in the winter, but that doesn’t mean you should skip it. This little artsy town is big on food, shops, and bookstores, not to mention the Tuck Inn, which is the perfect place to rest after a day of exploring. There’s so much to love about the town of Rockport, Massachusetts; in fact, you may just decide to relocate!
Rockport, MA, USA
Doug Kerr / Flickr
Next up on our list of some of the best small towns in Massachusetts to visit in winter is North Adams. From invigorating spring hikes to stunning fall foliage, North Adams has all kinds of seasonal appeal. But our state’s smallest city has a lot going on in the winter, too — come see for yourself.
North Adams, MA 01247, USA
kirbyfest / Flickr
Wellfleet was first settled in the 1650s, so it’s brimming with local history. This is an ideal destination for foodies — the seafood here is absolutely delightful. It’s one of our favorite small towns in Massachusetts for a quick weekend adventure.
Wellfleet, MA, USA
Speaking of spots that look like a Norman Rockwell painting, Deerfield is a great place to go when you need to get away from it all. Bundle up and take a picturesque walk down Main Street, which simply radiates old-fashioned charm. The historic district is actually considered to be an outdoor museum populated by 18th-century homes. Deerfield might just be one of the best-kept secrets in New England.
Deerfield, MA, USA
The former home of (you guessed it) Norman Rockwell makes a fantastic winter getaway. Take a tour of Arrowhead farm, Herman Melville’s former home, or Wheatleigh, a regal 19th-century mansion. At night, sip mulled cider by the fire at the Lion’s Den Pub. This picture-perfect destination in Massachusetts is one you won’t want to leave!
The Berkshires, United States
OnlyInYourState may earn compensation through affiliate links in this article.
Address: Northampton, MA, USAAddress: Stockbridge, MA, USAAddress: Rockport, MA, USAAddress: North Adams, MA 01247, USAAddress: Wellfleet, MA, USAAddress: Deerfield, MA, USAAddress: The Berkshires, United States
The OIYS Visitor Center
best small towns in massachusetts September 18, 2022 Beth C. What’s the most charming town in Massachusetts? Massachusetts makes for an excellent day trip destination in any season. While the above article mentions charming winter towns to experience, it’s also true that the Bay State is stunning in the summer. One of our favorite summertime getaways in Massachusetts is Cape Cod. This hook-shaped peninsula is infused with stunning scenery, coastal beauty, and small-town charm. From museums to bookstores, local shops, and delicious seafood restaurants, you’ll find no shortage of fun things to do in Cape Cod. If you’re looking for a day at the beach, head to Lighthouse Beach in Chatham. Across the way, you’ll see the picturesque Chatham Light. Also, don’t forget to stop by Briar Lane Jams & Jellies for a delicious Cape Cod treat to take home with you.
The OIYS Visitor Center
best small towns in massachusetts
September 18, 2022
Beth C.
What’s the most charming town in Massachusetts? Massachusetts makes for an excellent day trip destination in any season. While the above article mentions charming winter towns to experience, it’s also true that the Bay State is stunning in the summer. One of our favorite summertime getaways in Massachusetts is Cape Cod. This hook-shaped peninsula is infused with stunning scenery, coastal beauty, and small-town charm. From museums to bookstores, local shops, and delicious seafood restaurants, you’ll find no shortage of fun things to do in Cape Cod. If you’re looking for a day at the beach, head to Lighthouse Beach in Chatham. Across the way, you’ll see the picturesque Chatham Light. Also, don’t forget to stop by Briar Lane Jams & Jellies for a delicious Cape Cod treat to take home with you.
The OIYS Visitor Center
The OIYS Visitor Center
Massachusetts makes for an excellent day trip destination in any season. While the above article mentions charming winter towns to experience, it’s also true that the Bay State is stunning in the summer. One of our favorite summertime getaways in Massachusetts is Cape Cod. This hook-shaped peninsula is infused with stunning scenery, coastal beauty, and small-town charm. From museums to bookstores, local shops, and delicious seafood restaurants, you’ll find no shortage of fun things to do in Cape Cod. If you’re looking for a day at the beach, head to Lighthouse Beach in Chatham. Across the way, you’ll see the picturesque Chatham Light. Also, don’t forget to stop by Briar Lane Jams & Jellies for a delicious Cape Cod treat to take home with you.
