13 Picturesque Towns in Massachusetts You Should Explore

Massachusetts has vibrant cities like Boston, but it is in these small towns that New England is alive. From the small fishermen’s shelters along the coast to the cute storybook towns of the Berkshires, Massachusetts has towns with unique character and rich history.

Visiting these charming Massachusetts towns feels like going through a set of picture cards. Some towns are blessed with sandy beaches and fishing docks while some present panoramic views of mountain and comfortable inns. Here are some of the most picturesque towns in Massachusetts that are full of character.

Rockport

Rockport’s streets features art galleries, seafood restaurants, and painted cottages. You can visit Bearskin Neck, a narrow roadway packed with specialty stores and candy stores, which opens directly to the water. It is a perfect place to watch the sunset after a hectic day on the island.

Concord

Concord is known for Walden Pond where Thoreau lived and the Old North Bridge. This town has a lot to do with the American Revolutionary War. Historically, it is a quiet town for enjoying a walk, getting to know its beautiful streets, and for having a cup of coffee in quiet cafes.

Stockbridge

Stockbridge is one of the beautiful towns located in the Berkshires and has all the feels of the traditional art town. The town has the Norman Rockwell Museum where people can view art that depicts a classic America. The town itself seems like it could be out of a Rockwell painting, there are historical houses, small shops, and picturesque areas for a picnic. Every winter, Stockbridge tries to replicate the painting, “Main Street at Christmas” by Norman Rockwell and it is lovely during the holiday season.

Provincetown

Provincetown is the last town on the cape, and it is known by locals as P-Town. There are sandy beaches, several art galleries, Commercial Street with shops, seafood restaurants and an energetic buzz. Provincetown is also well known for festivals so you are likely to come across a parade or festival when in the town.

Lenox

A cultural center in the Berkshires, Lenox is the home to the summer venue of the Boston Symphony Orchestra, the Tanglewood. Apart from the arts, Lenox has beautiful inns, shops, and beautiful scenery. Its understated beauty and history, as well as the surrounding countryside, make it ideal for short breaks that include music and art.

Salem

A history of witch trials makes Salem a popular tourist attraction for people from all over the world. Salem has not shied away from witchcraft, in fact today there are museums, houses that have been turned into museums for witchcraft, and historical tours that give the feel of Salem witch trials. If you happen to be in Salem in October, you will be in the middle of Halloween festivities. Apart from the witchcraft myths, Salem has some great architecture, especially the maritime one, and there are numerous local shops and cafes.

Newburyport

Newburyport is a charming seaport with an active waterfront and a number of well-maintained Federal architecture homes. This is a historic port town and there are some great restaurants, shops and cafes to be found along the water’s edge. It is an ideal site for a boat cruise or for a leisurely walk on the specially laid brick roads. The Newburyport is most appealing for the historic and the lively community that makes it an ideal destination for a day trip.

Marblehead

Marblehead is a typical fishing town of New England and is steeped in charm. There are boats in its harbor and colonial architecture houses line narrow streets of the town. Fort Sewall is recommended for wonderful views of the sea or for those who like to walk, the historical district in Marblehead as nearly every building has history connected to it. This little town is perfect for history and beach lovers.

Nantucket

Nantucket is a beautiful island town with cobbled roads, houses with roses, and beautiful sandy beaches. Hire a bicycle to go around the island or take a trip to the Whaling Museum or grab a lobster roll and watch the ocean.

Great Barrington

Great Barrington is an interesting town in the area of Berkshires which has a rather relaxed atmosphere. With old and new farmers markets, locally owned restaurants featuring fresh and organic produce, restored independent bookshops and unique gift stores—travelers will find Great Barrington perfect for a weekend getaway.

Gloucester

Gloucester is one of the oldest seaports of the United States. This town has been fishing oriented for many years and the presence of the sea is seen throughout the town. Stroll through the Fisherman’s Memorial, taste fresh fish caught locally or watch whales aboard a whale-watching tour. Gloucester is an incredible coastal town with a thriving working waterfront and vibrant artistic scene.

Shelburne Falls

Shelburne Falls is a town in western Massachusetts and is most famous for the Bridge of Flowers – a trolley bridge that has been turned into a floral display. This is a picturesque small town with artistic shops like art galleries, old style shops and other stores and eateries. Shelburne Falls in particular has numerous attractions which might interest travellers due to the tranquil atmosphere created by the nearby Deerfield River.

Cambridge

Cambridge is actually a part of the Boston metropolitan area, but it is different in its own way. World famous for educational institutions including Harvard University and the Massachusetts Institute of Technology, Cambridge is intellectual and cultural. Harvard Square is a great place to shop for books or hang out in cafes and watch street performers or take a walk around the Charles River.

Disclaimer: This list is solely the author’s opinion based on research and publicly available information.

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