People dressed in costumes at the annual Haunted Happenings event in Salem, Massachusetts. Image credit Heidi Besen via Shutterstock

7 Most Memorable Small Towns in Massachusetts

Massachusetts. The name conjures up images of history and wonder, nature and entertainment. The landing place of the Mayflower is home to stunning colonial landmarks, the first public library in America, and the Salem witch trials. It is where tea met the sea in a strange protest, and wild turkeys roam free. Massachusetts, or Boston to be exact, is also home to a famous hike, the Freedom Trail, which passes 16 historic sites that played a role in the American Revolution. The first US railroad was built in this state, as well as the very first subway. This is the location from which JFK served as US Senator (he was also born in Massachusetts) and where Fenway Park and the Green Monster await fans during baseball season.

There is much to see and experience in Massachusetts for citizens and tourists alike. And the best place to start exploring is in the memorable small towns that highlight the best of what this gorgeous state has to offer.


The landmark Dexter Grist Mill and Water Wheel in Sandwich, Massachusetts.
Dexter Grist Mill and Water Wheel in Sandwich, Massachusetts.

Sandwich is the oldest town in the Cape Cod region of Massachusetts. With all the history and attractions this place offers, it begs for a stay longer than just one day. Visitors can grab a delicious coffee and pastry for breakfast at Beth’s Bakery and Café (housed in what used to be a Puritan church) before heading towards the Sandwich Glass Museum. The museum honors hundreds of years of glass-blowing by featuring beautiful glass pieces.

The historic trend continues at the Heritage Museums and Gardens, which contain peaceful gardens and fountains, a labyrinth, an old mill, and a stunning treehouse. The gardens are filled with rhododendrons and daylilies, while the gallery buildings offer a tour of American automobiles and folk art and a historic carousel that still works.

One of the most memorable places to visit in Sandwich is First Beach. The ocean gently kisses the edge of the sand on this small beach. For those looking to participate in beach activities, the Town Neck Beach off Town Neck Road offers fishing and swimming spots and skimboarding. There is also the Scusset Beach State Reservation Park, where visitors can enjoy expansive views of the Cape Cod Canal and Cape Cod Bay.


Downtown Orange, Massachusetts
Downtown Orange, Massachusetts.

Known as The Friendly Town, Orange is where visitors will find Lake Mattawa, a popular boating and fishing destination. Orange also boasts a riverfront park where people can launch their boats onto the Millers River. On the shores of the river are lots of space for picnicking and relaxing. The river is also great for canoeing and kayaking in season.

Visitors who want to encounter nature up close in Orange can visit the Tully Mountain Wilderness Management Area, where the lonely Tully Mountain stands. From the summit, Mount Monadnock and Mount Wachusett are in full view. Several hiking trails in Orange include mountain climbs, too.

Those who want to learn more about Orange’s history can take a day trip to Orange Memorial Park. Here, the Peace Statue honors Orange residents who served in the war. The 12-foot statue portrays a WWI soldier explaining the hopelessness of war to a child. The statue is punctuated by a bronze plaque that reads “It Shall Not Be Again.”


Man walking on stilts in the Wellfleet 4th of July Parade in Wellfleet, Massachusetts.
Man walking on stilts in the Wellfleet 4th of July Parade in Wellfleet, Massachusetts. Image credit Cindy Goff via

Creatives like artists and writers often flock to Wellfleet's magnificent beaches, searching for inspiration and solace. But this small town is popular for more than just its unforgettable landscapes. It is a surfer’s paradise with a bohemian vibe. The Wellfleet Harbor has that proper American small-town harbor look and offers panoramic views of the sea.

At Duck Harbor Beach, collect pretty rocks and shells while enjoying the spectacular sunset. Or hike the Great Island Trail on the Cape Cod National Seashore. There are short and long hikes to choose from, while those with stamina can hike the almost nine-mile trip to Jeremy Point, which is only visible during low tide.

Wellfleet also prioritizes entertainment for its visitors and residents with the fun Drive-In Theatre, where you can watch movies, take a round of mini golf, and visit a seasonal flea market.


Overlooking Marblehead, Massachusetts.
Overlooking Marblehead, Massachusetts.

Marblehead is chockful of historic sites, making it an absolute haven for history enthusiasts. Along the crooked streets, majestic houses still stand. The town is the location of Old Burial Hill, the Old Powder House, and the Jeremiah Lee Mansion. Marblehead is a popular day trip and vacation spot for Boston visitors, just 17 miles from the city. Back in the day, 1629 to be exact, colonists turned Marblehead into a beautiful fishing village.

Today, the fishing village charm remains, inspiring tourists and residents to linger longer at the rocky shoreline or in the historic downtown area. The Old Town House in the center of Market Square once served as the place for pre-revolutionary war meetings. Just outside downtown, the majestic Fort Sewall still overlooks the Marblehead Harbor.

Those who want to experience more of the outdoors in Marblehead can take a brisk walk to Gerry Island. The rocky path to the island is only visible for two hours during low tide, so travelers need to check the tide schedules.


People dressed in costumes at the annual Haunted Happenings event held during the month of October in celebration of the town's history of witch trials and Halloween.
Annual Haunted Happenings event held during the month of October in Salem, Massachusetts. Image credit Heidi Besen via Shutterstock

Salem is a mere 10-minute drive from Marblehead. Marblehead provided a home for Wilmott Redd, who was the only town woman to be hanged after being convicted of witchcraft in 1692. Salem is where travelers can learn even more about the witch trials and see the houses and buildings that remain from that time. Chestnut Street is lined with historic mansions for all to see, while the Salem Witch Trials Memorial is a poignant reminder of those who were executed.

Salem is also where the iconic House of the Seven Gables still stands. Formerly known as the Turner House, this gorgeous but spooky abode now operates as a nonprofit museum.

Visitors who love all things creepy will enjoy the History and Hauntings of Salem tour or perhaps the darker Mysteries and Murders of Salem tour. The eerie atmosphere intensifies over Halloween and somewhat dissipates by Christmas when visitors come for the Christmas Parade, Winter Market, and candlelit tours of the Witch House.

There are also plenty of outdoor activities in this unique town. Travelers can enjoy a trip to Waikiki Beach at Winter Island Park or a boat tour to Bakers Island Light Station. The eerie Salem Woods is an adventure on its own, while the cheerfully named Dead Horse Beach offers free parking and kayaking.


Families enjoy a summers day on Front Beach, just steps from downtown Rockport, Massachusetts.
Families enjoy a summers day on Front Beach, just steps from downtown Rockport, Massachusetts. Image credit James Kirkikis via

Rockport doesn’t have as much of a witchy history, but visitors will find practical delights like lobster boats and traps at the harbor. And, Motif #1 is one of the main reasons people visit Rockport. The little red fishing shack pops up on thousands of Instagram and Pinterest accounts and is a popular spot to stop and take a picture.

Other than Motif #1, there are scenic bike rides to enjoy around Cape Ann and 30 art galleries to explore. Visitors who want to get their daily steps in can do so on the incredible trail system on the north shore. Day travelers who wish to explore the craggy coastline can bring their kayaks. Back Beach offers memorable diving spots for scuba divers. And those who visit Rockport at the perfect time (whale watching season is from April to October) may spot a couple of whales in the sea surrounding Cape Ann.

History enthusiasts can go for a cruise on the 65-foot historic schooner Thomas E. Lannon, while adrenaline junkies will be thrilled by the non-active Rockport quarries with the opportunity to dive into the cool water on a hot day.

Oak Bluffs

Carpenter Gothic Cottages with Victorian style, gingerbread trim on Lake Avenue, Oak Bluffs on Martha's Vineyard, Massachusetts.
Carpenter Gothic Cottages, Oak Bluffs on Martha's Vineyard, Massachusetts. Image credit Wangkun Jia via

Oak Bluffs, known for being the largest Martha’s Vineyard marina, is an absolute haven for day trippers from the city. The town is famous for Ocean Park, a wide-open green space with a bandstand. It is where the annual fireworks display and the kite festival happen.

Near Ocean Park, off Seaview Avenue, Inkwell Beach awaits. Inkwell Beach is close to the ferry dock and has lifeguards during the summer. State Beach is perfect for strolling and has access to the infamous Jaws Bridge, where the namesake 1975 movie was filmed. Visitors can dive into the water here without fear of Bruce coming after them.

Oak Bluffs is great for families, especially because it is home to the oldest platform carousel in the US. The Flying Horses Carousel still operates in the summer and maintains its original horsehair manes and glass eyes. Moreover, there are paddleboard and kayak adventures to be had before exploring the 19th-century gingerbread cottages at the Oak Bluffs Campground.

Massachusetts towns offer one-of-a-kind experiences that big city dwellers yearn for. There are histories to be unraveled, unique natural sights to gape at, and fantastic places to explore. Cliché as it may sound, there is something for everyone in each town, from skydiving to ziplining, from beach strolling to hiking in the woods, to building campfires and searching for ghosts of times gone by.

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