The Commonwealth of Massachusetts is a gem of the Northeast United States. The Puritans, some of the earliest English colonizers to make their way to North America in 1620, were entranced by the land’s mountains, meadows, and bay views. So entranced, in fact, that they built their new homes amid the bounty of Massachusetts' beauty. In 1788, Massachusetts became an official member of the United States.
Massachusetts has a booming tourism industry. On your trip to Massachusetts, you can visit the locations where some of your favorite movies were filmed in cities and small towns alike. Check out the sites of Revolutionary War battlefields all across the state. Catch a game at the oldest major league baseball stadium in the country, Boston’s Fenway Park. Join the millions of people who flock to Massachusetts year after year for its rich history and mesmerizing scenery.
It is okay if you are feeling a little overwhelmed by all the possibilities of your Massachusetts itinerary. I certainly was! Read on to find out about the 14 most beautiful small towns in Massachusetts you should visit. Whether you’re a passionate hiker, history buff, or film lover, Massachusetts has a small town that will be your home away from home!
Adams is a quaint paradise located in the valleys of Berkshire County, a fifteen minute drive from the New York and Vermont state borders. This town was founded in 1778 and has a population of 8,166. When you visit Adams, you can take your pick of adorable bed & breakfasts to stay at. Take a stroll through town to see some beautiful old buildings (be sure to check out the architecture at the Adams Free Library!) before you head out for a picnic in Savoy Mountain State Park. Enjoy the stunning views of the Hoosac Range to the east and Massachusetts’ highest peak, Mount Greylock, to the west.
While you’re soaking in the sights in Adams, you can also visit the Susan B. Anthony Birthplace Museum and the Quaker Meeting House. Take the family to the Adams Summer Movies Under the Stars film series, or catch a live show at The Adams Theater!
Now, let’s head out east and check out Salem! Salem was settled in 1626 but not officially incorporated until 1836. Salem is probably one of the most beautiful small towns in the entire United States, and its 44,480 residents live there for good reason. Psychics and mediums throughout the town offer readings to visitors interested in mystery and magic. Explore the dark and complicated history of this town at one of its many museums. They’ve got witches and pirates and pioneers, oh my! After getting a lesson on Salem’s history, take your pick of peaceful parks to stroll through. For the morbidly curious, I highly recommend taking a cemetery tour to find out about the interesting folks who have lived and died in Salem.
Take in the sea air at one of the many beautiful beaches along the Salem Sound. You can even take a boat ride out to Baker’s Island for a tour of the 10-acre light station. Camp out overnight by the lighthouse if you’re feeling truly adventurous!
Topsfield, founded in 1650, is home to a charming rural community of 6,613 residents just 25 miles north of Boston. This quiet town has been around longer than the United States has had independence from English rule. Topsfield boasts several highly sought after wedding venues for a reason. While Topfield’s farms and wineries are some of the most beautiful spots in the country, they only scratch the surface of Topsfield’s splendor.
Topsfield is also home to a river wildlife sanctuary that you have to see to believe. Explore forests and meadows filled with some of the coolest animals the United States has to offer. On your trip to Topsfield, you have to take a canoe down the meandering Ipswich River to see this sanctuary in all its glory.
Back to the sea! Gloucester is a beautiful town nestled in the middle of an Atlantic Ocean sandwich, with beautiful bays on the north and south. Many of its 29,952 residents' families have lived in the Gloucester area since its founding in 1642. In 2023, CNN named Gloucester one of the best 15 cities and towns in all of America. I can see why! This town is one of the oldest in the country, and its residents stay there for good reason.
I’ve actually been thinking about moving to Gloucester to visit the beaches, get involved in the town’s bustling working waterfront, and eat fresh seafood (straight from the ocean!) every single day. On a quick visit, I recommend whale watching. Make sure you save time to tour one of Gloucester’s several lighthouses and castle museums. This small town packs a BIG punch.
Sailing over to another coastal town, Newburyport was founded in 1851 and is home to 18,295 people. This charming river town opens up to the Atlantic Ocean. Gorgeous beaches and fascinating maritime history museums will certainly keep you busy during your visit. What sets Newburyport apart is Maudslay State Park, which boasts spectacular plant and animal life to explore year round.
Plant lovers and tree huggers will fall in love with the gardens at Maudslay State Park. The park features 19th century gardens and plantings, massive pine trees, and rolling meadows like nothing you have ever seen. This beloved park is also home to one of the Massachusetts’ largest stands of mountain laurel.
Let’s head back inland (do not worry, we are not going far!) to little old Rochester, home to 5,717 people. Another town from the dawn of the United States, Rochester was founded in 1686 and has a fascinating history of shipbuilding and whaling trade. These days, this rural town has become a charming farm community.
Snipatuit Pond, located in Rochester, is the perfect place for a gentle afternoon of kayaking and fishing. If you really want to get your hands dirty, head over to Haskell Swamp Wildlife Management Area for gorgeous hiking trails, hunting, trapping, and birdwatching. This quaint small town has so much natural beauty to explore!
Near the Masschusetts/New Hampshire border you will find the town of Westford and its 24,296 residents. This beautiful town, founded in 1729, feels like the setting of a Hallmark movie, with an active community and family fun for every season! This is the perfect destination for ocean-wary travelers, because Westford has two town beaches along their gorgeous freshwater ponds.
In May, Westford hosts an Apple Blossom Festival. You will want to come back in June for their Strawberry Festival, too! Explore Westford’s natural glory at The Butterfly Place, or go horseback riding at one of the town’s stunning ranches. In the colder months, you can also play in Westford’s winter wonderland at the Nashoba Valley Ski Area. Westford truly has something for everyone!
Shelburne Falls may be the most beautiful village in the country. It is a historic village founded back in 1768, with museums and views worth a cross-country trip to explore. Shelburne Falls has a population of 1,659. Shelburne Falls features must-see attractions that you will have a hard time finding anywhere else!
Long ago, Shelburne Falls was a trolley town. These days, their trolley bridge is the Bridge of Flowers, covered in floral life that changes with each season. Take a quick walk from the Bridge of Flowers to find the coolest part of Shelburne Falls: the Glacial Potholes. There are more than 50 whirling pools and rock carvings at the base of Salmon Falls, formed thousands of years ago.
Film lovers, listen close! The entire state of Massachusetts is a massively popular destination for filmmakers, and Ipswich is featured in some of my favorite movies. Visit the castle and beach at Crane Estate, one of the locations used in Little Women (2019), The Equalizer (2014), The Thomas Crowne Affair (1968), and more! Ipswich was founded in 1634 and 13,176 call this town their home.
Ipswich is also home to a playground of breweries and bakeries, orchards and farms, and the Great Marsh Important Bird Area! This town’s landscape is so stunning, and there’s always something to do. Follow the Ipswich River out to the bay, where you can take a trip out to Sandy Point State Reservation for beautiful ocean sights and wildlife viewing.
Another popular film production location, the town of Harvard (not to be confused with Harvard University in Cambridge, MA) is straight out of a dream. Settled in 1658 and incorporated in 1732, Harvard now has a population of 6,610. Author Louisa May Alcott lived in Harvard for a time during her childhood, and actually based some parts of Little Women on her time living off the land in this town! Visit the Fruitlands Museum in Harvard to see where her family lived and learn about their experimental community.
Other sights to see in Harvard include healing gardens, several breathtaking apple orchards, and the Harvard Annual Flea Market!
Another fun fact about Harvard: One of the earliest US writing instrument manufacturers, the Benjamin Ball Pencil Company, was based in Harvard, MA! Their pencils are extremely rare and worth thousands of dollars today.
If you were in high school (or parented a high schooler) during the Broadway debut of Hamilton (2015), the name Charles Lee might be familiar to you. While he and the nation’s founding fathers did not necessarily get along, this gorgeous town named after him in central Berkshire County gets along with everyone! Lee was founded in 1777 and is home to 5,788 people.
Lee boasts classic US architecture (right down to Joe’s Diner). The Lee Library is a must-see, with a huge historical collection and its own fascinating history. The library is the only remaining Cambridge library building in the Berkshires. Lee is also home to historical museums about homes and railways, and you need to take a dip in Lee’s serene Laurel Lake. Lee is everything we love about the Berkshires!
Take a drive down the winding roads of Carlisle, founded in 1805, in autumn and you will see why this town earned a spot on this list (and why its 4,852 residents stay there)! Book your stay at one of Carlisle’s charming inns, and chat with the locals about the best eateries in town.
The real selling point in Carlisle is the Great Brook Farm State Park. The 1000-acre park hosts an active dairy farm with an ice cream stand! Aside from the farm, this park also features 20 miles of hiking trails, Native American historical landmarks, and cellar holes left by English colonial settlers in the 1600s. Come back in the winter to explore Great Brook State Park on skis at the Great Brook Ski Touring Center, which cares for 10+ miles of beautiful ski trails.
Tyngsborough is the perfect weekend getaway and a rural farming paradise. Home to 12,380 residents, Tyngsborough was founded in 1809. The town’s distinctive green bridge, built in 1930, will get you across the Merrimack River and into an adventure in agriculture.
Stroll through any of the several farms to find incredible produce, huge pumpkins, and some of the cutest animals Massachusetts has to offer. Parlee Farms has a petting zoo, so you can make friends with baby goats, sheep, and silly chickens! Make sure to wind down at the spa before the end of your trip!
We’ll wrap this up back on the coast. Brewster, settled in 1656 and incorporated in 1803, is a small town of 10,318 residents in Barnstable County with fairy tale architecture and luxurious beaches. Check out an open house at the Crosby Mansion, built in 1888. Crosby Mansion is one of the coolest places I’ve ever seen, with mesmerizing building details (hello, curved staircase!) and a spectacular view of the sea.
From the mansion, you will need to hit one of Brewster’s beaches and go for a swim in Cape Cod Bay. Paine’s Creek Beach boasts fascinating rock structures that reveal themselves with the tide. If you are not into the ocean, head over to Nickerson State Park. There, you will find quiet trails for hiking and wildlife viewing along with a large lake that is just perfect for kayaking.
Hopefully, you’ve been taking notes to share with your travel agent, because we just added 14 stops to your itinerary! These are the 14 most beautiful small towns in Massachusetts. You should visit them as soon as possible. I hope you have a great time on your trip! Who knows, we might even run into each other!