
These 10 Towns Are Massachusetts's Best-Kept Secrets
The Massachusetts coastline, dotted with beautiful, seaside spots like Martha’s Vineyard and Cape Cod, is a common summer escape for many Americans. What you may not realize is that Massachusetts is also home to dozens of lesser-known retreats. With populations under 10,000, these small towns are the perfect spot to avoid holiday crowds, while still enjoying delicious seafood and stunning landscapes. Each of them has its own rich history and endearing quirks, just waiting to be discovered. So, pack your bags and head to the American northeast to uncover the best-kept secrets of Massachusetts!
Oak Bluffs

According to the 2020 census, about 5,000 folks call Oak Bluffs home throughout the year. This tiny town on the sea is located on the island of Martha’s Vineyard and has been made famous for its colorful, gingerbread-cottage style homes. Oak Bluffs is rich in African American history; you can visit the home of African American writer, Dorothy West, or the Villa Rosa, a beautiful mansion dedicated to MLK. He actually spent time at the historic villa.

After taking in the beautiful architecture, head to the Flying Horses Carousel. It is the oldest continuously operating carousel in the United States! It is also right by the Oak Bluffs Harbor, where you can charter a fishing boat or simply take in beautiful views of the sparkling sea. This area is also where you can find restaurants, like The Sweet Life Cafe and The Barn Bowl and Bistro. For a relaxing vacation, spend your afternoon getting lost in the local boutiques, like Island Life Studio along Circuit Avenue in the town center.
Chatham

Chatham, located in Cape Cod, was incorporated as a town in 1712 and has emerged as a mainstay for summer travelers. The Chatham Lighthouse is a historic symbol of the oceanside town. It is also a beautiful spot to take in uninhibited views of the Atlantic.

If you want to spend more time outdoors, check out Monomoy National Wildlife Refuge or the Cape Cod Rail Trail. The former offers scenic trails for wildlife spotting, while the latter is great for bikers and walkers who want to enjoy Chatham’s landscape. During the summer, Chatham also hosts a summer concert series, so be sure to do a quick search before your trip to ensure you don’t miss any of the local performers!
Ipswich

Named after Ipswich, England, Ipswich, Massachusetts, is located in Essex County, about 30 miles north of Boston proper. It is home to Willowdale State Forest and Sandy Point State Reservation, making it a nature lover's dream!

Made famous for its clams, Ipswich hosts an annual Chowderfest downtown with over 35 vendors and local musicians. After you have had your fill of clam chowder, head to Crane Beach to enjoy 1,200 acres of beach and dunes. If you prefer creature comforts over the outdoors, head over to Market Street and enjoy the small boutiques and restaurants full of locally made goods and cuisine.
Hyannis

Hyannis is a small village located in Cape Cod. It also serves as a great jumping off point to other areas in Massachusetts like Nantucket and Martha’s Vineyard since it offers a ferry to both harbors. Hyannis is a beautiful, relaxing destination year-round, but its main tourist season is the summer. If you find yourself there in the winter, be sure to check out their Polar Express!
This small, northeast town punches well above its weight class in attractions. It is home to a plethora of restaurants and shops on its one-mile main drag. For casual seafood fare, try The Black Cat Tavern. Keltic Kitchen is a favorite local restaurant for a traditional Irish breakfast. They even have a little Irish shop in the back! If you are traveling with little ones, the nearby Pirate Cove Mini Golf is a great and fun way to spend an afternoon. Beachgoers can head to Veterans Beach to enjoy a day soaking in the rays or wading in the sea.
Stockbridge

Stockbridge is one of the smaller towns in the state, home to just over 2,000 people. For dining, make a reservation at Once Upon a Table if you are in the mood for delicious, new American food. They offer both lunch and dinner service.

Stockbridge’s most famous attraction is the Norman Rockwell Museum. This museum is a must-see; they also host several family-friendly events throughout the year. After a museum trip, drive to the Berkshire Botanical Garden to enjoy the fresh air and local wildlife. For lodging, try the historic Red Lion Inn located on Main Street. The hotel was founded in 1773 and absolutely oozes charm!
Great Barrington

Great Barrington is one of the few towns that is almost as busy in the winter as it is in the summer. If you are visiting in the winter, head to the slopes at Ski Butternut for a day of snowboarding and skiing. When you get off the mountain, meander down Main Street and marvel that you are walking down the first Main Street to boast electric lighting.

Great Barrington is southern Berkshire’s largest town, located along the Housatonic River. Walk along the riverwalk and marvel at the small town’s history. A town of firsts, Great Barrington is the site where the first slave was freed, as well as the site of the first armed resistance against the British.
Williamstown

Williamstown is located in Berkshire County, just a stone’s throw from Vermont to the North and New York to the West. From biking and golfing to perusing the Clark Art Institute and Williams College Museum of Art, this small town has no shortage of activities.

Williamstown has a history as an agricultural town, making it the perfect spot for farm-to-table dining. Try The Barn Kitchen & Bar and Mezze Bistro + Bar for unique and delicious offerings. The winter season offers as many activities as the summer, including snowshoeing or skiing at the Berkshire East Mountain Resort. Be sure to pack your base layers before you head out to enjoy the fresh air, as it gets chilly!
Edgartown

Located on Martha’s Vineyard, Edgartown was once a major whaling port, but is now a carefully preserved seaside escape. This classic New England village is the perfect place to unwind by the ocean year-round. Edgartown hosts several events, including Pink & Green Weekend in May, 4th of July Fireworks & Parade, Bass in the Grass in September, Martha’s Vineyard Food & Wine Festival in October, and Christmas in Edgartown.

If you feel like splurging on accommodation, plenty of locally owned bed and breakfasts can be enjoyed in this small seaport. Once you arrive, head to the Edgartown Harbor Lighthouse or Joseph Sylvia State Beach to enjoy the natural beauty and views of the sea.
Rockport

Rockport has a population of roughly 7,000 people and offers a romantic getaway just 40 miles north of Boston. Before you arrive, be sure to download the Rockport, MA Walking Map from the town’s official website; this will help you navigate the hidden gem of a town!

After you check in to your hotel, take a walk down the seaside village’s Main Street or Bearskin Neck. Along their main drag, you will find one-of-a-kind shops like Denim Blanket Company and the Rockport Candle Company. Rockport also has a buzzing art scene. Be sure to check out the Rockport Art Association & Museum and the Art Nook Gallery. Art buffs will notice a familiar building in Motif Number 1, the most painted building in America.
Lenox

The tiny village of Lenox is located in the Berkshires and offers everything you could want in a country retreat. Whether you go in the heat of summer or the dead of winter, try staying in an adorable, locally-owned bed and breakfast.

After you have settled into your new digs, walk to Nejaime’s Wine Cellars. They will prepare a custom cheese plate and recommend a delicious bottle of wine for you to pair alongside it. With a belly full of cheese, you may consider heading further down Main Street to The Bookstore and Get Lit Wine Bar; this is a book shop and wine bar in one! After your day of food and wine, take a walk through the Pleasant Valley Wildlife Sanctuary for your Daily dose of Vitamin D.
There is nothing wrong with taking a trip to the major cities in Massachusetts, like Boston or Cambridge, but on your next trip to the northeast, consider spending a couple of days in one of these lesser-known gems. These best-kept secrets in Massachusetts offer the perfect opportunity for a romantic winter getaway, family summer vacation, and everything in between. Take the scenic route as you explore these villages and hamlets, virtually undisturbed by swaths of vacationers. You may never visit a bustling metropolis again!