8 Must-Visit Small Towns in Massachusetts

Concord

If you’re looking for one town not to skip during your journey to see the must-visit small towns in Massachusetts, it is the town of Concord. Founded in 1635, Concord is rich in history, especially that dating around the time of the Revolutionary War. For instance, the Battles of Lexington and Concord were fought in this town, as well as another of the must-visit small towns in Massachusetts. 

Interestingly enough, in 2012, Concord became the first community in all of the United States to ban the sale of single-serving water bottles. This ban was met with mixed responses in the community, with national coverage.

Rockport

Explore the best of Massachusett’s seaside with Rockport. This small town is located on the eastern end of Cape Ann. Because of its unique shape and location, Rockport is surrounded by water on three sides.

As of the 2020 census, Rockport had a population of 6,992. It has been used as the set for various films and television shows, including The Next Karate Kid (1994) and The Proposal (2009), the latter of which had Rockport stand in for the town of Sitka, Alaska.

Sandwich

Of the must-visit small towns in Massachusetts located on Cape Cod, Sandwich is the oldest community. While still small compared to the other cities and towns in Massachusetts, with a population of 20,259 as of 2020, Sandwich is one of the larger towns listed here. However, while there may be more people, Sandwich’s ample history and sights are worth the trip.

The motto for Sandwich is “Post tot Naufracia Portus,” which means “after so many shipwrecks, a haven.”

Oak Bluffs

Oak Bluffs is a small town in Massachusetts with a big reputation. In 2020, the census showed that only 5,341 people lived in Oak Bluffs. However, while it sports a small year-round population, this little town on Martha’s Vineyard is a popular vacation destination.

During the summer, visitors flock to this must-visit town for its beautiful beach scenery and lovely natural atmosphere. One of its most notable features is the 19th-century buildings, with the architecture of many of these buildings being reminiscent of cottages.

It was also popularized in the movie Jaws!

Nantucket

Nantucket is fairly remote when compared to other must-visit small towns in Massachusetts. It is located 30 miles south of Cape Cod, a small island. Here, it stands as the most southeastern town in the entire New England region.

For much of the year, Nantucket has a population of 14,255 as of 2020. However, during the summer months, this can rise to nearly 80,000, as this is one of the most popular towns to visit in Massachusetts.

Lenox

Many of the must-visit small towns in Massachusetts are located on the coast, showing off the most that the New England seaside has to offer. Lenox, however, is located in the far western region of the state, in Berkshire County.

With a population of only 5,095 (2020), Lenox offers a quiet and quaint escape. It is the home of Shakespeare & Company, as well as several small villages. Because of this, during peak seasons of the year, it can transform into a popular tourist destination.

Lexington

For those interested in the history of the United States and the Revolutionary War, there is no town better to visit than Lexington. This is because Lexington is home to the “Shot heard ’round the world,” the first shot in the Revolutionary War that occurred on April 19, 1775.

This must-visit small town in Massachusetts is abundant in historical points of interest. However, Lexington has other features and places to offer as well, being rich in culture and art.

Wellfleet

At a 2020 population of 3,566, Wellfleet is one of the smallest of the must-visit small towns in Massachusetts. However, despite its quiet winters, this number can grow in the summer, with nearly 18,000 people visiting during the peak months of summer. 

Wellfleet is best known for its oysters. In fact, this town is home to the October Wellfleet OysterFest, an annual festival celebrating the town’s abundance of oysters. Much of the area of Wellfleet is under protection, with a large portion of the town being a part of the Cape Cod National Seashore.