8 Undiscovered Small Towns in Massachusetts
Sandwiched between the bustling cities of Boston and Worcester are sleepy little towns just waiting to be discovered. These hidden gems are what New England is all about! From sandy beaches to Victorian estates and lush forests, there’s something here for the whole family. Plan an autumn road trip and hit up apple orchards in Stow, or take a train ride through the Berkshires in Lenox. Or plan a summer retreat in Wellfleet to admire the breathtaking stretch of coastline in Cape Cod. As you’ll soon discover, each of these towns delivers a unique and welcoming charm.
Montague
Discover the natural beauty of New England in Montague. Amid the lush forests of Wendell State Forest and Montague Plains Wildlife Management Area is the sleepy little town of Montague. In the heart of the historic downtown district is Montague’s claim to fame- the Montague Bookmill. Its slogan, "Books you don't need in a place you can't find," is what the town is all about. This delightful bookstore hosts a cafe and art galley, and it’s nestled in a reclaimed 19th-century gristmill with amazing views of the Sawmill River.
The town is composed of five unique villages worth exploring: Montague Center, Millers Falls, Lake Pleasant, Montague City, and Turners Falls. While each village delivers a unique charm amongst the 19th-century buildings, Turners Falls is special. It offers amazing views of the Turner Falls Canal (built in the 1700s) and is home to the Great Falls Discovery Center, which gives visitors more insight into the area.
Stow
If you are planning an autumn Massachusetts road trip, stopping by Stow is a must. Famous for its apple orchards, visitors from all over the state travel to Stow for a day of fall-themed fun. Stop off at one of their famous orchards, such as Honey Pot Hill, Shelburne Farm, and Carver Hill Orchard, for a day of apple picking, hay rides, and farm stands. And don’t forget to try a cider donut before you go.
The downtown area of Stow is a charming blend of classic New England architecture, filled with locally owned shops and charming diners. To spend more time in nature, head to the Assabet River National Wildlife Refuge. Admire the changing leaves, or walk one of their many trails. For water views, Lake Boon is an excellent spot to fish or go for a swim during the hotter summer months.
Harvard
The sleepy town of Harvard has a rich history and a strong Shaker foundation. The Harvard Shaker Village was once a thriving Shaker community and is now a historical site where visitors can walk the preserved buildings for a glimpse into Harvard's past. The downtown area of Harvard, also known as the Town Common, hosts old-world buildings like the Harvard General Store. It’s a great spot to shop local pastries, grab a cup of coffee, and go for a stroll down the charming 19th-century streets.
On the outskirts of town are amazing spots to unwind, such as The Fruitlands Museum. It’s a quaint museum nestled on the Nashua River Valley that has Shaker and Native American artifacts to learn more about the area. The museum also has accessible nature trails so you can take in the amazing views. Head to the Carlson Orchards for a day of apple picking in the fall or Bare Hill Pond in the summer to fish, boat, or swim.
Hadley
Hadley is one of the oldest farming communities in the United States. Its location on the Connecticut River has made it rich for farming for over 350 years. Its primary crop, asparagus, is so famous that it’s earned the nickname Hadley Grass. The rolling landscape is peppered with farm stands, giving visitors a unique opportunity to taste their famous asparagus for themselves.
While Hadley is known for its wide open spaces and rolling acres of farmland, the downtown district gives visitors a unique opportunity to travel back in time. The North Hadley Village Hall lies in the heart of town. Take a tour of this stunning building, or partake in one of the many community events held within. To admire the scenery surrounding this hidden gem, make sure to head to Skinner State Park or the Mount Holyoke Range for a full day of hiking, biking, or birdwatching.
Oak Bluffs
Located within Martha’s Vineyard, the town of Oak Bluffs is New England charm at its finest. The downtown area hosts amazing 19th-century architecture and brightly painted Victorian cottages, also known as “Gingerbread Cottages.” One look, and you’ll realize why they earned that nickname! The cottages are located within the Oak Bluffs Campground, a former religious camp meeting site. Today, you can have the rare opportunity to rent a cottage, but you have to act fast because they book quickly.
Nestled on Lagoon Pond, the Oak Bluffs Harbor is a popular spot among locals and visitors. Filled with cozy shops and cafes, it’s a great place to explore the area and take in harbor views. The harbor is also famous for Jaws Bridge, which became famous after its appearance in the movie Jaws. With so many attractions and beaches (like Inkwell Beach and Eastville Beach), Oak Bluffs is a perfect summertime retreat.
Stockbridge
The sleepy town of Stockbridge is the ideal blend of natural beauty and charming city streets. There’s no better example of Stockbridge’s charm than the Norman Rockwell Museum. The famous artist lived in Stockbridge for the last 25 years of his life, and the town inspired some of his work. The museum showcases some of his works, as well as exhibits teaching visitors more about the famous artist.
Another great spot in Stockbridge is the historical estate of Naumkeag. While the mansion is spectacular, the surrounding Chinese Garden overshines the estate. Visitors can walk the gardens, and take self-guided tours of the estate. For more beauty, take a short drive to Monument Mountain. A short hike delivers stunning panoramic views of the Berkshires, and it’s a must-see for visitors!
Lenox
If you love magnificent architecture, you have to add Lenox to your Massachusetts bucket list! It’s home to spectacular mansions and estates such as the Ventfort Hall Mansion and Gilded Age Museum. However, the most famous estate in town is The Mount, home to author author Edith Wharton. Visitors can take a guided tour of the estate and walk through the meticulously maintained gardens.
To take in the beauty of the Berkshires, head to Berkshire Scenic Railway Museum. The museum details Lexox’s transportation roots but also offers rides on vintage trains. Lenox is also home to Tanglewood which is the summertime home to the Boston Symphony Orchestra. It’s a great place to take in the fresh air and enjoy the view at the 500-acre venue.
Wellfleet
Located on the sandy beaches of Cape Cod is the rustic town of Wellfleet. Famous for its beaches, Wellfleet offers visitors a little bit of everything. If you enjoy flat, sandy shores, head to Marconi Beach and Wellfleet Town Beach. If you love the rugged beauty and dramatic scenery, check out Race Point Beach and Longnook Beach. As a thriving little beach town, Wellfleet is famous for its oysters. Be sure to order a plate at one of their local restaurants! For a real treat, plan your visit during the Wellfleet OysterFest and enjoy oysters amid live music and family-friendly activities.
To learn a little more about this eclectic beach town, stop by the Historic Wellfleet Center and Museum. It’s located in the stunning 19th-century town hall and gives visitors a glimpse into Wellfleets maritime history. If you want to relax and unwind in nature, the Wellfleet Bay Wildlife Sanctuary offers visitors beautiful hiking trails and plenty of opportunities for wildlife photography.
Massachusetts may be the 7th smallest state in the country, but the best things often come in small packages! With sandy beaches along the Atlantic Ocean and magnificent forests just waiting to be explored, these small towns are Massachusetts at its best! Take tours through amazing estates like The Mount in Lenox or jump off the Jaws Bridge in Oak Bluffs for a day of swimming. No matter what time of year you find yourself in Massachusetts, these small and friendly towns are a great way to explore the Bay State.
