Historic and Picturesque Massachusetts Towns

Massachusetts is one of the places where modern American history began. It is where the first colonies began when the Mayflower landed near Provincetown. It is a state that can trace its European history back hundreds of years, further than anywhere else in the country. It isn’t just one or two places in Massachusetts with an extensive colonial history; it is almost everywhere. Towns like Maynard, Norfolk, Marblehead, and Lynn are just some of the many incredible Massachusetts towns with rich histories.

From Plymouth to Westford, there are more historic Massachusetts towns than anyone could name. Let’s explore some of the most picturesque and historical Massachusetts towns, with colonial and early American histories.

Let’s start with Concord, Hingham, and Ipswich. Concord is a town just northwest of Boston. It is well-known amongst history buffs for the nearby Minute Man National Historical Park, which was a significant Revolutionary War battle site. Today, this nearly 400-year-old town is a picturesque community home to just under 20,000.

Hingham is a coastal South Shore town located along Hingham Bay leading out into the Atlantic. The town was first settled over 400 years ago and has a rich colonial history you’ll find numerous remnants of. Ipswich is a town further north in the state located along the Atlantic. It is home to about 14,000 residents and is a quaint and pleasant town with great seafood, a beach, and a history that can be traced back to its founding in 1634.

Other great towns include Watertown, Medford, and Salem. Watertown, which is just west of Cambridge, is a popular Boston suburb that is known for its affluent community. It is an upper-class small town that is safe with a quiet suburban feel. It is a minor commute to Boston, with many Watertown residents working in the city but living in the smaller community.

Medford is located just seven miles from downtown Boston along the Mystic River. It is a busy suburban city home to roughly 60,000 residents. It also is the site of Tufts University, so it has a young population. North of Boston, you’ll find the famed city of Salem. Salem’s past is dark, as it was the site of the 1692 Witch Trials, which still shocks the nation to this day. The town has a colonial look and numerous museums and experiences dedicated to its lurid past.

Next, we have Gloucester, Lexington, and Quincy. Gloucester is a North Shore city on Cape Ann. It is a picturesque, classic New England community with a maritime look. There are lighthouses, fishing boats, and of course, delicious seafood. Lexington is a town northwest of Boston and east of Sudbury. It is known as the place where the first shot of the American Revolutionary War was fired. It is a pivotal part of U.S history and has a deeply colonial look with numerous museums and monuments. Quincy is a major city south of Boston that sits on Quincy Bay. It is a suburb of Boston but a major city in its own right, home to over 100,000. It has great shopping, restaurants, and nearby New England scenery.

Stockbridge, Chatham, and Northampton are three more historic communities within the state. Stockbridge is on the far west end of the state near the New York border. It is in the Berkshires, a nature-filled area with gorgeous sights, and is the site of the Norman Rockwell Museum, which features great works from the 20th-century master.

Chatham is located on the far east end of continental Massachusetts, across the water from Nantucket. It is a coastal community known for its beaches, lighthouse, and hiking trails. It is the perfect place for lovers of ocean landscapes. Northampton is a pretty city of almost 30,000, located in central Massachusetts. Northampton is a former industrial and trade center that has become a cultural hotbed. It draws in residents for the delicious food scene within the town and the affordable cost of living.

Lastly, we have Sturbridge, Newburyport, and New Bedford. Sturbridge is a small and historical town that borders Connecticut to the south. Home to roughly 10,000 residents, it is a quiet place with a history stretching back hundreds of years. That history is commemorated in Old Sturbridge Village, a living museum replica of the town in the 1830s.

Newburyport is a coastal city not far from the New Hampshire border that includes small parts of Plum Island. It is a historic seaport with a major tourism industry due to the beaches, ocean views, and the picturesque look of the town. New Bedford is a city of over 100,000 residents. It is located on Buzzard’s Bay, across the water from Naushon Island. New Bedford is a historic whaling and fishing hotspot with a thriving downtown filled with shops, restaurants, and museums.