Top 15 Charming Small Towns to Explore in Massachusetts

One of the original 13 colonies, Massachusetts is currently the most populous state in New England. The Pilgrims established the first colony in Plymouth, while the neighboring town of Salem was the site of the notorious witch trials.

Massachusetts boasts a rich historical significance along with stunning countryside and coastal towns, making it a desirable vacation spot for a myriad of travelers. Escape from the bustling city to unwind for a few days.

Explore our compilation of the preeminent small towns to visit in Massachusetts:

1. Stockbridge, Massachusetts

Stockbridge, situated in Berkshire County, is an all-season resort area characterized by its artistic and scenic beauty. Initially settled by missionaries in 1734, they created a mission for Native Americans who earned this territory as a reward for their allegiance to the British during the French and Indian Wars. Over time, Stockbridge has evolved into a prime retreat for relaxation.

The town’s allure is significantly boosted by its legacy as an art colony. Norman Rockwell created much of his artwork here, and the town hosts the Norman Rockwell Museum. Wander through the charming downtown, enjoy the Berkshire Botanical Gardens, explore local art exhibitions, or consider participating in a yoga session at the Kripalu Center for Yoga and Health where familiar scenes from Rockwell’s paintings may come to life!

2. Hadley, Massachusetts

Hadley, located in Hampshire County, is a compact town well-liked by visitors for its strategic position along Route 9. With a robust history dating back to its settlement by Puritans in 1659, Hadley links back to the witch hunts of its era; Mary Webster, spouse of one of Hadley’s founders, was tried and acquitted of witchcraft right here!

Fortunately, the town has not conducted trials for centuries. Nonetheless, visitors can enjoy its picturesque downtown or shop at Hampshire Mall. The renowned University of Amherst is also in proximity. Consider a stay at Hadley Meadow Bed and Breakfast, ideal for unwinding after a day of hiking at the Silvio O Conte National Fish and Wildlife Refuge. Step back into history at the Porter Phelps Huntington House Museum and disconnect from the modern world during your stay in Hadley.

3. Provincetown, Massachusetts

Provincetown, a charming New England town situated at the tip of Cape Cod, is a coastal resort renowned for its beaches, harbor, and vibrant artistic community, contributing to its tourism appeal. The Cape Cod region was first explored by Europeans in 1602, named for the codfish that frequented the waters. In 1620, the Pilgrims anchored here in the harbor, drafting and signing the Mayflower Compact. Although they later settled across the bay, Provincetown continues to attract visitors due to its rich history and inviting beaches.

When visiting Provincetown, explore the Pilgrim Monument, engineered by Willard Sears, which echoes the Torre del Mangia in Siena. The town features 8 buildings and two historic sites listed on the National Register of Historic Places; do not miss the Provincetown Historic District and the Dune Shacks of Peaked Hill Bars Historic District! As a historic artists’ colony, Provincetown has ingrained itself in promoting alternative lifestyles and gay tourism. Participate in various town festivals such as the Portuguese Festival, Bear Week, or PBG’s Carnival Festival, ensuring to apply sun protection before enjoying the beaches!

4. Rockport, Massachusetts

Rockport, nestled in Essex County approximately 40 miles from Boston, was once an uninhabited area of Cape Ann. It began to develop in the 1800s due to granite exportation and stone quarrying. Although the demand for granite eventually waned, Rockport’s artist colony has helped to shape it into a favored vacation destination.

Tourists flock to Rockport for its iconic rocky shorelines. Stroll down to the harbor to witness the famed red fishing shack, Motif Number 1, which has inspired countless artists and continues to attract aspiring painters. Be sure to savor the local lobster; lobster fishing is a staple of the local economy. Explore Halibut Point State Park to see an old granite quarry and Babson Farm before heading to Bearskin Neck, where former fisherman shacks have been transformed into delightful eateries and galleries. Capture some memories through photographs or revisit your artistic side by painting your experiences!

5. Westford, Massachusetts

Another historically significant town, Westford, located in Middlesex County, holds noteworthy ties to the Revolutionary War: Paul Revere’s son attended school here, and both a bell and a weather vane created by him are housed in the town. Presently, Westford has transformed into a vibrant suburban community, where residents enjoy a high quality of life, a fact that becomes immediately evident during your visit.

A plethora of charming annual events attract visitors to Westford: a snow sculpture contest in winter, an Apple Blossom Parade and Carnival in May, and a Strawberry Festival in June, to name a few. Bring your skis or enjoy delicious ice cream at Kimball Farm. There is truly something for everyone here!

6. Newburyport, Massachusetts

Newburyport is an ideal locale for sailing enthusiasts, located in Essex County approximately 35 miles outside of Boston. This historic seaport along the Merrimack River served as a commercial hub for shipping, fishing, and shipbuilding. While sailing remains an important part of the local economy today, recreational boating also contributes significantly.

As you explore this historic town, visit the first Coast Guard station, the Cushing House Museum and Garden, and the Newburyport Superior Courthouse, which is the oldest continuously active courthouse in Massachusetts. Enjoy some ice skating year-round, and wander the scenic waterfront and boardwalk. The quaint downtown shopping district abounds in boutiques, ensuring Newburyport delivers something enjoyable for every visitor, including those who may be prone to seasickness.

7. Rowe, Massachusetts

Rowe is a small town with a population of fewer than 400 residents in Franklin County, Massachusetts. Historically, this area was frequented by Native Americans for fishing and foraging before being established as a fort for settler protection against raids. Today, Rowe remains enveloped in natural beauty and is also home to New England’s first nuclear power plant.

Take a stroll to Village Green and Mill Pond, where you will be greeted by the picturesque Adams Mountain. For those eager to explore beyond the town limits, consider visiting the railroad bridge spanning the Deerfield River, where tranquility awaits. Hiking trails at the Upper Bear Swamp Reservoir and Pelham Lake, as well as Monroe State Forest, provide excellent opportunities for outdoor activities. Rowe’s remoteness offers an ideal chance to escape everyday concerns and enjoy an enriching retreat.

8. Oak Bluffs, Massachusetts

Located on Martha’s Vineyard, Oak Bluffs invites visitors to experience its charming gingerbread cottages and historic 19th-century buildings. Named for the oak groves overlooking Nantucket Sound, Oak Bluffs appears to have been meticulously designed for your visit!

Take pleasure in the stunning views from the Ocean Park Gazebo, letting the ocean breeze refresh you. Enjoy a few nights at the historic Oak Bluffs Inn, and treat yourself to delicious cuisine at Nancy’s Restaurant. Relax on Inkwell Beach or take a paddleboard on the gentle waves. Remember, enjoyment is the primary goal, and Oak Bluffs facilitates that effortlessly.

9. Lenox, Massachusetts

Lenox, a small town in Berkshire County, has garnered a reputation as a popular summer destination. Initially an industrial town, it flourished as an art colony in the 1800s, with notable figures such as Catharine Sedgwick and Nathaniel Hawthorne residing there. Following the arrival of the railroad, tourists began to flock to the town.

Today, visitors are drawn to Lenox for its scenic streets and to immerse themselves in Tanglewood, the summer residence of the Boston Symphony Orchestra. Beyond being a favored summer haven for outdoor enthusiasts, Lenox shines in autumn, inviting hikes and bike rides around Pleasant Valley Sanctuary to witness vibrant foliage. Winter also holds its allure, featuring various ski resorts in the vicinity. Throughout the year, pamper yourself at the Cranwell Spa for rejuvenating treatments.

10. Concord, Massachusetts

Situated in Middlesex County, Concord is part of the Greater Boston area. The town center is positioned at the convergence of the Sudbury and Assabet Rivers, forming the Concord River and serves as a historic site from the Battle of Lexington and Concord, the inaugural conflict of the American Revolutionary War. This significant town also possesses a rich literary heritage, as it was home to notable writers such as Ralph Waldo Emerson, Nathaniel Hawthorne, and Louisa May Alcott.

Discover Concord’s historic battleground or tour the preserved residences of these literary icons. Intriguingly, the Concord grape was developed here, and the community was the first to prohibit single-serving plastic bottles. As you stroll down Main Street, you will quickly appreciate the unique charm of this bold town. Don’t miss the Minute Man National Historical Park, Walden Pond State Reservation, and the Sleepy Hollow Cemetery. Enjoy some relaxation along the Concord River and savor a meal at 80 Thoreau before continuing your discovery of this Massachusetts treasure.

11. Norfolk, Massachusetts

Norfolk is a suburban, rural town located in Norfolk County, peacefully nestled in a valley along the Charles River. Initially established to populate the colonial frontier, the area was deemed too isolated despite its fertile lands and excellent fishing opportunities, leading to its abandonment and eventual resettlement due to the rise of textile mills.

Experience Norfolk as a tranquil and secluded destination. You may recognize some film locations from Ted 2, which was shot here. Wear your hiking shoes to explore the Stony Brook Wildlife Sanctuary, a splendid way to connect with nature. Enjoy a meal at the Horse N Carriage or unwind over drinks at the Eagle Brook Saloon.

12. Maynard, Massachusetts

Maynard, positioned along the Assabet River in Middlesex County, is named after Amoy Maynard, an entrepreneur who obtained water rights to the river during the mid-1800s. The mill he developed produced a significant portion of wool for U.S. military uniforms during the Civil War. Although the mill faced eventual bankruptcy, it has been preserved and transformed into a commercial hub with the town. The clock tower here houses the oldest operational hand-wound clock in the United States and takes 1-2 hours to wind manually!

As you explore Maynard, you will be enchanted by its local shops, including an establishment aptly named “Charmed.” Attend a delightful performance at the Fine Arts Theatre Place, and if fishing is of interest, stop by Maynard Outdoor Store to gather supplies.

13. Manchester-by-the-Sea, Massachusetts

Manchester-by-the-Sea is an enchanting town on Cape Ann known for its picturesque beaches and scenic vistas. Established in 1939 by European settlers, this area has a rich history as a fishing community spanning over 200 years, but transitioned into a summer resort after the arrival of the well-known poet Richard Dana in the mid-1800s. This led to the fashionable crowds from Boston venturing out to this serene location to enjoy the refreshing ocean breezes.

Spend a day at Singing Beach where the sand produces a unique sound as you walk across it! Take a hike or simply admire the renowned Eagle Head rock, perfect for both climbing and photography. Don’t overlook the downtown area, particularly the Town Hall. This summer, indulge in a delightful escape along the stunning coastline.

14. Groton, Massachusetts

Groton, also located in Middlesex County, was initially established as a trading post and is known for its battlefield significance during King Phillip’s War, a series of conflicts between Native Americans and European settlers. Almost all structures in Groton were burned during this time.

Today, Groton has beautifully recovered and offers numerous recreational activities. Savor a delightful meal at the Herb Lyceum at Gilson’s or enjoy a coffee at the Blackbird Café. Take a stroll along the Gibbet Hill Barn and Trails, or canoe down the river with Nashoba Paddler. If you visit during autumn, don’t miss the hidden gem, Autumn Hills Orchard!

15. Deerfield, Massachusetts

Situated in Franklin County, Deerfield was regarded as the farthest northwestern outpost for New England settlements until the mid-18th century. Nestled in the Connecticut River Valley, it bore witness to numerous skirmishes between Native Americans and European settlers during the early colonization of the United States.

Today, Deerfield honors its heritage through Historic Deerfield. Wander through its charming streets and visit the Old Deerfield Country Store or the Memorial Hall Museum. Venture out to Pocomtuck Ridge for a rewarding hike with scenic views. Your calorie expenditure can always lead to delightful treats at Richardson’s Candy Kitchen upon returning to town!