The 15 Most Charming Small Towns in Massachusetts

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Massachusetts is a large and diverse state and while its cities like Boston offer a lot, especially when it comes to historical and cultural attractions, there are many alluring small towns too. Enjoy scenic natural beauty, rich history, outdoor activities, and more with destinations along the coast, in the mountains, and in between. By visiting the charming destinations on this list, you’ll discover everything from places that recreate pilgrim life in the 17th century to seaside retreats.

 

Stockbridge
Stockbridge, MA

Stockbridge

Located in the beautiful Berkshires and famous for being one of the world’s most beautiful destinations for fall foliage, Stockbridge is a postcard-perfect town in every season. In modern times, it’s known for being spotlighted in “The Real Housewives of New York City,” but what describes it better is the connection to Norman Rockwell, the renowned painter who spent his final 25 years taking inspiration from its beauty. It’s home to the Norman Rockwell Museum which holds the world’s largest collection of original Rockwell art, and visitors can also explore a Gilded Age mansion and the Naumkeag, a botanical garden at the former country estate of a notable New York City lawyer.

Rockport
Rockport, MA

Rockport

Rockport looks like a postcard that’s come to life. Overflowing with charm, it’s beautiful year-round, though many come to enjoy the fall colors or for a summer getaway. Located at the tip of the Cape Ann Peninsula, it offers miles of soft sandy beaches along with some of the best hiking in the Northeast. With its seaside location, it’s a great place to kayak or even scuba dive while fresh local seafood, including lobster rolls, is plentiful. Halibut Point State Park offers trails along the water that deliver fantastic views that stretch well into New Hampshire and Maine. You’ll find plenty of art galleries and shops to explore too.

Shelburne Falls
Shelburne Falls, MA

Shelburne Falls

A popular weekend getaway in Massachusetts, the village of Shelburne Falls is actually made up of two towns, Shelburne and Buckland with the Bridge of Flowers that spans the Deerfield River connecting them. Today, the bridge is a popular photo-op and you’ll find more to enjoy along the streets with their fine examples of Victorian architecture. There are lots of shops where local, handmade artisan items can be purchased, including hand-blown glass, along with fabulous art galleries to explore.

Oak Bluffs
Oak Bluffs on Martha's Vineyard, MA

Oak Bluffs

Picturesque Oak Bluffs, which sits along the northeastern shore of Martha’s Vineyard, stands out as one of Massachusetts’ best places to visit with its vibrantly painted gingerbread cottages that give it a storybook feel. An attraction in their own right in the late 1800s, they’ve been passed down through generations and many are still owned by the same family. The Flying Horses Carousel, a national landmark that’s been spinning since 1876, is a must-ride as the country’s oldest carousel. There are some great beaches to spend the afternoon or an entire day at too. As they face Vineyard Sound, the surf is typically minimal, providing calm water for swimming and wading.

Salem
Salem Witch Museum in Salem, MA

Salem

One of the most fascinating historic towns, Salem is also rather charming, embracing everything from its pirate past to the infamous witch trials and colonial heritage. Watch re-creations of the trials and learn more about its history at the Peabody Essex Museum. The country’s oldest continuously operating museum, it’s a world-renowned institution of art that opened in 1799, when museums were officially known as a “cabinet of natural and artificial curiosities.” As a former hub of the China Trade and major port, you’ll see many stately homes that were built for wealthy merchants and sea captains as you stroll the streets, while its literary connection as the birthplace and home of Nathaniel Hawthorne can also be explored at the Nathaniel Hawthorne House.

Gloucester
Eastern Point Lighthouse historic building in Gloucester, MA

Gloucester

Located on Massachusetts’ northern coast along the southern shores of Cape Ann, Gloucester has had an active fishing harbor since colonial times. Its Eastern Point Lighthouse, erected in 1823, is one of the most famous lighthouses on the eastern seaboard. It was featured in the movie “The Perfect Storm,” which chronicles the story of the Andrea Gail, a commercial fishing vessel that was lost at sea. Visitors can also tour Hammond Castle, built in the 1920s to resemble a medieval castle, complete with flying buttresses and turrets. There are many historic homes to discover along with harbor sightseeing cruises, whale watching boat tours, and deep-sea fishing charters to join.

Plymouth
Plimouth Plantation

Plymouth

Founded in 1620, Plymouth may best be known as the site of the landing of the Pilgrims who were fleeing religious persecution in Britain. Plymouth Rock is said to mark the very spot, although there is some dispute about the claim. But you’ll find much more than the “rock” here in this seaside town, including a full-scale replica of the Mayflower with tours led by costumed guides. The must-visit is Plimoth Plantation, a living history museum where you can experience Plymouth just as it was in the 17th-century.

Sturbridge
Old Sturbridge Village in Sturbridge, MA

Sturbridge

One of the most historic towns in the state, Sturbridge is home to the Old Sturbridge Village, the Northeast’s largest outdoor living history museum. Here you’ll get a good glimpse of life in the 1830s, complete with costumed guides. There are many unique boutiques and antique shops to browse through, along with opportunities for outdoor activities. Wells State Park, just outside of town has a picturesque pond for fishing, canoeing, or summer swimming, along with 12 miles of scenic trails.

Falmouth
The sign that welcomes you into charming Falmouth, MA

Falmouth

The second largest town on the Cape, a visit to Falmouth reveals many charms, with everything from waterfront seafood shacks and sandy beaches to the picturesque Nobska Lighthouse. There are wildlife refuges and conservation areas for hiking and kayaking, while the 10.7-mile Shining Sea Bikeway is a great place to cycle, with views of ponds, salt marshes, cranberry bogs, and farms. In historic Falmouth Village, you’ll find museums, unique shops, and a wide range of eateries. During the summer, it hosts a weekly farmer’s market along with arts and crafts fairs.

Provincetown
Provincetown in Cape Cod, MA

Provincetown

Located at the very tip of Cape Cod, seaside Provincetown offers more than 30 miles of beaches, vast sand dunes, and plenty to do right in town. A haven for artists and the LGBTQ crowd, it’s welcoming to all. It has a rich creative history as the country’s oldest continuous art colony and has many galleries to explore along with outstanding restaurants, seafood shacks, fudge shops, other fun stores, and a wide range of entertainment options.

Concord
Minute Man National Historical Park - Concord, MA

Concord

One of the state’s prettiest towns, Concord is best known as the site where the first battle of the Revolutionary War took place. The quiet main street is lined with historic buildings while the stars and stripes are proudly displayed hanging from lamp posts and above doorways. At Minuteman National Historic Park, enjoy picnicking and hiking, while Walden Pond offers a fabulous photo-op, made famous by writer Henry David Thoreau. The Old North Bridge was where the first successful armed resistance to British rule occurred in 1775, with the current bridge being a replica that crosses the Concord River in the same spot. Check out the Old Manse House overlooking the river too. It was built by poet Ralph Waldo Emerson’s grandfather.

Lenox
Downtown Lenox, MA

Lenox

Nestled in the Berkshires, not only does Lenox make a great base for outdoor adventure with spectacular surrounding scenery and fall leaf-peeping, but it offers attractions like The Mount, which was the home of Gilded Age American novelist Edith Wharton. There are fun shops to browse, multiple fine dining restaurants, like The Portico and Table Six, and performing arts theaters. It also hosts Tanglewood, the headquarters of the Boston Symphony Orchestra in the summer.

Nantucket
The beautiful Nantucket shore

Nantucket

Nantucket is one of the most iconic summer getaways on the east coast. The island off the coast of Cape Cod attracts visitors of all types, particularly the well-heeled, with its pretty cedar-shingled beach homes, wind-swept dunes, beautiful beaches, and lighthouses. You’ll find cobblestone streets to stroll, upscale boutiques to browse, and plenty of seafood eateries for dining. The beaches along the south shore offer unforgettable sunsets and big waves, while Children’s Beach has calm waters where little ones can splash around.

Maynard
The historic Assabet Woolen Mill and clock tower

Maynard

Located along the Assabet River just 22 miles west of Boston, Maynard is named after businessman Amoy Maynard who purchased water rights to the river in the mid-19th century. After constructing a mill, he went on to make the highest percentage of wool for US military uniforms during the Civil War. While it ultimately went bankrupt in later years, it’s been well-preserved and now serves as the commercial center for the town. It includes a clock tower with the country’s oldest still operating hand-wound clock, requiring up to two hours to wind. There are also some great shops, eateries, and performances to enjoy at Fine Arts Theatre Place too.

Manchester-by-the-Sea
Manchester-by-the-Sea, MA

Manchester-by-the-Sea

Enchanting Manchester-by-the-Sea is located on Cape Ann, offering picturesque beaches, like Singing Beach, and a beautiful harbor. The downtown area has plenty of charm too. As a historic fishing village, sprawling homes are perched over rocky shorelines with vast lawns and ocean views. You’ll also find enticing shops and eateries downtown, along with opportunities to get out onto the water and even take a sailing lesson.

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