What comes to mind when you think of a small town? Perhaps a tight-knit community, a small downtown, and a slower pace of life? Well, there are numerous small towns in Massachusetts that are worth paying a visit to. And we have put together this list of 12 tiny towns around the state, one for each month of the year, that we think you should visit.

January: Hancock

Sswonk/Wikimedia Commons The town of Hancock is the perfect place to start your year off right. Why? Well, it’s home to Jiminy Peak Mountain Resort where you can experience plenty of winter fun like skiing, snowboarding, and a mountain coaster. The town of Hancock itself is home to fewer than 800 people but offers plenty of gorgeous scenery for all to enjoy. Hancock, MA, USA

February: Princeton

Massachusetts Office Of Travel & Tourism/Flickr The small town of Princeton is where you’ll find Mount Wachusett. Spend some time skiing and snowboarding or you can even go for a hike. Princeton also has a gorgeous public library with an interior you must see and you can go horseback riding or take a sleigh ride at Cornerstone Ranch. This is one town where you can truly enjoy the great outdoors all winter long! Princeton, MA, USA

March: Scituate

C Hanchey/Flickr The town of Scituate is situated between Boston and Plymouth. It may not be as popular a beach town as the ones on Cape Cod or Cape Ann, but it’s as picture-perfect as can be. Visit Scituate Lighthouse and the harbor for great photo ops, stop by the brewery, and visit one of the town’s museums. Head to the Scituate Chamber of Commerce website for more information. Scituate, MA, USA

April: Charlemont

C Hanchey/Flickr If you’ve ever driven along the Mohawk Trail, chances are you’ve been through Charlemont. With its location on the Deerfield River, Charlemont is absolutely beautiful. It’s also home to the Bissell Covered Bridge and the Zoar Outdoor Adventure Resort for some ziplining fun. Charlemont, MA, USA

May: Wellesley

Jameslwoodward/Wikimedia Commons Most famous for Wellesley College, the town of Wellesley is actually much more than just a college town. Set outside Boston, this community feels worlds away from city life. If you’re here in the month of May, check out the Wellesley Collge Greenhouses and the Massachusetts Horticultural Society’s Garden at Elm Bank. Visit the Charles River Regional Chamber website for more information. Wellesley, MA, USA

June: Essex

Elizabeth Thomsen/Flickr Just north of Boston on Cape Ann, Essex is a charming coastal community that offers visitors plenty of shops, galleries, restaurants, and outdoor spaces to explore. Head to the Visit Essex MA website to learn more. Essex, MA, USA

July: Provincetown

Ted Eytan/Flickr As one of the best small towns in Massachusetts, Provincetown is an exciting place to be in the summer. Not only does this town have some gorgeous beaches but a lively downtown area unlike any you’ve visited before! Provincetown, MA, USA

August: Chatham

Irishman19/Wikimedia Commons As one of America’s most walkable small towns, Chatham is as charming as can be. Peruse the shops and restaurants and then head to Monomoy Island and Chatham Lighthouse to take in the scenery. Chatham, MA, USA

September: Sudbury

Massachusetts Office Of Travel & Tourism/Flickr The town of Sudbury has a rich history that dates back to 1639 when it was incorporated. One of the most famous historical landmarks in town is the Wayside Inn Grist Mill located on the same property as the Wayside Inn. It’s worth a stop here to explore the property or even have a picnic! Sudbury, MA, USA

October: Adams

John Phelan/Wikimedia Commons The lovely town of Adams is located in a valley in the Berkshires. A visit here in October will grant you some of the best fall foliage views in the state. You’ll also be in close proximity to Mount Greylock and the Hoosac Valley Range. Adams, MA, USA

November: Plymouth

Massachusetts Office Of Travel & Tourism/Facebook Visit Plymouth, the first settlement of the Pilgrims back in 1620. Here is the town where the first American Thanksgiving was held, so it’s certainly ideal to visit in November. Stop by Plymouth Rock, the Mayflower II, and the Plimoth Patuxet Museums, which are the top historical sites in town. Plymouth, MA, USA

December: Stockbridge

Visit Stockbridge Massachusetts/Facebook Home to Norman Rockwell for many years, Stockbridge is one of the top Christmas towns in America. A visit here in December is sure to put you in the holiday spirit as the town goes all out with festivities and decor. Stockbridge, MA, USA

 

Sswonk/Wikimedia Commons

The town of Hancock is the perfect place to start your year off right. Why? Well, it’s home to Jiminy Peak Mountain Resort where you can experience plenty of winter fun like skiing, snowboarding, and a mountain coaster. The town of Hancock itself is home to fewer than 800 people but offers plenty of gorgeous scenery for all to enjoy.

Hancock, MA, USA

Massachusetts Office Of Travel & Tourism/Flickr

The small town of Princeton is where you’ll find Mount Wachusett. Spend some time skiing and snowboarding or you can even go for a hike. Princeton also has a gorgeous public library with an interior you must see and you can go horseback riding or take a sleigh ride at Cornerstone Ranch. This is one town where you can truly enjoy the great outdoors all winter long!

Princeton, MA, USA

C Hanchey/Flickr

The town of Scituate is situated between Boston and Plymouth. It may not be as popular a beach town as the ones on Cape Cod or Cape Ann, but it’s as picture-perfect as can be. Visit Scituate Lighthouse and the harbor for great photo ops, stop by the brewery, and visit one of the town’s museums. Head to the Scituate Chamber of Commerce website for more information.

Scituate, MA, USA

If you’ve ever driven along the Mohawk Trail, chances are you’ve been through Charlemont. With its location on the Deerfield River, Charlemont is absolutely beautiful. It’s also home to the Bissell Covered Bridge and the Zoar Outdoor Adventure Resort for some ziplining fun.

Charlemont, MA, USA

Jameslwoodward/Wikimedia Commons

Most famous for Wellesley College, the town of Wellesley is actually much more than just a college town. Set outside Boston, this community feels worlds away from city life. If you’re here in the month of May, check out the Wellesley Collge Greenhouses and the Massachusetts Horticultural Society’s Garden at Elm Bank. Visit the Charles River Regional Chamber website for more information.

Wellesley, MA, USA

Elizabeth Thomsen/Flickr

Just north of Boston on Cape Ann, Essex is a charming coastal community that offers visitors plenty of shops, galleries, restaurants, and outdoor spaces to explore. Head to the Visit Essex MA website to learn more.

Essex, MA, USA

Ted Eytan/Flickr

As one of the best small towns in Massachusetts, Provincetown is an exciting place to be in the summer. Not only does this town have some gorgeous beaches but a lively downtown area unlike any you’ve visited before!

Provincetown, MA, USA

Irishman19/Wikimedia Commons

As one of America’s most walkable small towns, Chatham is as charming as can be. Peruse the shops and restaurants and then head to Monomoy Island and Chatham Lighthouse to take in the scenery.

Chatham, MA, USA

The town of Sudbury has a rich history that dates back to 1639 when it was incorporated. One of the most famous historical landmarks in town is the Wayside Inn Grist Mill located on the same property as the Wayside Inn. It’s worth a stop here to explore the property or even have a picnic!

Sudbury, MA, USA

John Phelan/Wikimedia Commons

The lovely town of Adams is located in a valley in the Berkshires. A visit here in October will grant you some of the best fall foliage views in the state. You’ll also be in close proximity to Mount Greylock and the Hoosac Valley Range.

Adams, MA, USA

Massachusetts Office Of Travel & Tourism/Facebook

Visit Plymouth, the first settlement of the Pilgrims back in 1620. Here is the town where the first American Thanksgiving was held, so it’s certainly ideal to visit in November. Stop by Plymouth Rock, the Mayflower II, and the Plimoth Patuxet Museums, which are the top historical sites in town.

Plymouth, MA, USA

Visit Stockbridge Massachusetts/Facebook

Home to Norman Rockwell for many years, Stockbridge is one of the top Christmas towns in America. A visit here in December is sure to put you in the holiday spirit as the town goes all out with festivities and decor.

Stockbridge, MA, USA

There you have it — a list of small towns in Massachusetts, one for each month of the year. What are some of your favorite charming small towns in the state? Let us know in the comments.

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