11 of the Most Charming Small Towns to Visit in Massachusetts
Massachusetts is a commonwealth in the New England region of the United States. Though the bustling metropolises of Boston and Springfield are well known, hundreds of smaller towns throughout the Commonwealth are full of charm and character. These small towns dot the state from the mountain ranges of the Central and Western regions to the historic towns of Merrimack Valley.
From seaside towns to small fishing villages, Massachusetts is brimming with history, culture, and nature. These eleven towns are among the most charming in Massachusetts.
Northampton
Northampton is on the Connecticut River and enjoys a vibrant art scene. It is home to Smith College, a top-rated women's liberal arts school. Smith College also has a museum with Pablo Picasso's works on display, as well as several other museums like the Calvin Coolidge Presidential Library.
The Historic District comprises the Parsons, Shepard, and Damon Houses and covers 2.5 acres downtown. The Historic Northampton organization preserves artifacts that accentuate the town's past. It offers several programs, including guided tours down Main Street, where people can learn about the town's past. Northampton is a friendly town with natural beauty and a rich history.
Gloucester
Gloucester is a famous fishing village on Cape Ann Island that has been swordfishing since the early 17th century. The seaport was established in 1823 and is the oldest in the nation. The town is entwined with its storied maritime history, including a Fisherman's Memorial statue by the harbor that honors those lost at sea. One of the most notable maritime tragedies in recent years was the loss of the Andrea Gail in the fall of 1991, memorialized in the novel and the movie A Perfect Storm.
The Cape Ann Museum includes work from maritime artist Fitz Henry Lane from the 20th century. Along with the rich maritime history, many historical homes and museums, like the Hammond Castle Museum, were built in 1926. The Sargent House Museum is a Georgian-style residence built in 1782 and home to many sailors and patriots. It is a unique way to experience the history of Gloucester.
Newburyport
Newburyport is a historic seaport just north of Boston. The quaint town is reminiscent of a movie set, and Plum Island, home to beautiful beaches, is only a short drive from downtown. Market Square is the main hub of the brick buildings that make up the downtown area and is renowned for its many shops.
Tannery Marketplace is another shopping destination considered one of the best on the North Shore. Downtown also has a waterfront park where shoppers can take in stunning views of the waterfront. Of course, since Newburyport is a coastal town, there are also plenty of maritime activities. At Newburyport Harbor, Yankee Clipper tours sail around the harbor and the Merrimack River.
Wellfleet
Wellfleet is on Cape Cod and is known for its shellfish. The coveted Wellfleet Oyster is so popular that an annual oyster Fest celebrates this tasty treat. The historic downtown village (Main Street) is a cultural hub and the center of the shops and restaurants.
The natural landscape is dotted with salt marshes, dunes, and freshwater ponds left by ice glaciers eons ago and has been protected since 1961. The Atlantic White Cedar Trail is one of the prettiest natural attractions in Wellfleet, winding through a pine and oak forest to mature woodlands. The Wellfleet Cultural District has linked downtown with a historic harbor through a walking loop where pedestrians can experience the best of the town's past and present, adding to Wellfleet's natural charm.
Oak Bluffs
Oak Bluffs is on historic Martha's Vineyard and is one of the island's main destinations for summer guests. The small town has several "gingerbread cottages" and 19th-century architecture. The signature structure is the East Chop Lighthouse, so-called since the 17th century. The word "chop" was the English designation for an entryway to a navigable channel.
Oak Bluffs has many beaches, so it is a popular summer destination. The Flying Horses Carousel is a landmark and the oldest platform carousel in the US, operating since 1884. This quaint town is best seen on foot, so you can experience the historic beaches and sites before enjoying a seafood dinner at one of the waterfront restaurants.
Provincetown
Provincetown is a historical port town on Cape Cod and was the landing site of the Mayflower in 1620. Today, it is a sought-after culinary and LGBTQ destination with a vibrant art scene. Seafood is the main fare here, and you can find great selections at the Atlantic House, Bayside Betsy's, and others.
Ptown, as it is lovingly known, is a certified Massachusetts Cultural District that includes notable art galleries like the Adam Peck Gallery and the Egeli Gallery. The Provincetown Art Association and Museum has been around for over 100 years and represents local artists with programs and continuing education courses. Ptown is a sophisticated coastal town brimming with culture and artistic talent that would top any destination list for Massachusetts.
Lenox
Located in Western Massachusetts, Lenox is a charming town with several historic mansions and museums. The Ventford Hall Mansion is a Jacobian and Gilded Age Museum once inhabited by the Vanderbilts. The Mount was designed by notable author Edith Wharton in 1926, and both are on the National Registry of Historic Places.
Another interesting museum is the Berkshire Scenic Railway Museum, built in 1984, where exhibits and even train rides are available. As for charming outdoor activities, the Mass Audobon's Pleasant Valley Wildlife Sanctuary is 1,405 acres of pristine woodlands and seven miles of hiking trails. Lenox is a serene town with stunning architecture and natural beauty, making it one of Massachusetts's most charming towns.
Sturbridge
Sturbridge is a classic town home to the Old Sturbridge Village, a living reenactment of an 1830s New England town. Old Sturbridge Village has period-dressed actors, exhibitions, and water-powered mills that take visitors back in time. The Tantisques, named after the Native Americans who once resided here, is now a 57-acre preserve and historic location. It is a destination spot for hikers and history buffs alike.
Due to its geographical location, Sturbridge came to prominence in the early 19th century as a transit hub. The town has been around since the 1600s and quickly became known as the "Crossroads of New England." Today, Interstate 90 meets US Route 20 here, and the town remains an important crossroads between Boston, Connecticut, and New York.
Woods Hole
Woods Hole is home to the Woods Hole Oceanographic Institute, one of the world's most prestigious research institutes. Historically, Woods Hole was one of the most important ports in New England thanks to its location on the southern end of Cape Cod. The Woods Hole Historical Museum is an ideal way to discover the historical importance of Woods Hole.
There is a notable downtown area where you can book a walking tour at the visitors center, which provides insights into the town's significance as a research facility. Water Street is the main thoroughfare, where you can find the ferry and restaurants like Landfall and the Water Street Kitchen. Woods Hole is a quiet harbor town with plenty to explore, and the research facility's academic air only adds to this historic town's charm.
Concord
Concord's historical contributions cannot be overstated. It was the first land-bound Puritan settlement and home to the first American Revolutionary War battle site. Minute Man National Historic Park includes several war sites and memorials. A Minute Man statue forever memorializes a significant battle at the North Bridge.
Notable authors Ralph Waldo Emerson, Nathaniel Hawthorne, and Henry Thoreau frequented Waldon Pond. In the 19th century, Emerson drafted "Nature" while staying at the Old Manse. The Old Manse is now open to the public as a museum with views of the Concord River in the background. Concord is truly a unique town, filled with American and literary history, and one of Massachusetts's best towns to visit.
Nantucket
Located on Cape Cod, Nantucket is an isolated island popular with summer vacationers. The island town's homes are made with classic architectural styles like Neo-Georgian, Federal, and Georgian. Along with the beautiful architecture, the cobblestoned streets lead you to the Town of Nantucket, with sophisticated dining options and beautiful views of the Atlantic Ocean.
The island was an important whaling center in the 19th century, and the Whaling Museum celebrates this history with artifacts and exhibits. The Nantucket Atheneum is a historical site and public library that draws 50,000 visitors annually. Other noteworthy sites include the Brant Point Lighthouse and the Grant Point Lighthouse, both historical structures built in the 1800s.
These eleven towns are not only beautiful but also historic and charming. Towns like Concord offer more history than most, while Woods Hole is known for its research center and stunning views. While these towns embrace their past and carefully preserve it, they also offer modern amenities like dining and shopping.
Providence has an incredible food scene, and Newburyport is a shopping hub. Sturbridge is like visiting two towns at once because of the living history section known as Old Sturbridge. Whether you are looking for exceptional seafood, sailing trips, or pleasant towns to explore, these towns have it all.
