This little fishing village is the perfect fusion of classic, coastal charm, and an inspiring art colony. No matter if you want to spend a relaxing weekend by the sea, are craving some fresh seafood, or just want to stroll along one of the state’s most scenic harbors in various fishing towns in Massachusetts, Rockport can definitely deliver. Here’s a selection of some lovely things to do in Rockport, Massachusetts.

Take a look at the sheer beauty of this coastal town:

For more Massachusetts charm, check out this amazing fall foliage train ride.

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The Best Towns in Massachusetts

What are the most historical towns in Massachusetts?

The most historical towns in Massachusetts include:

  • Boston. A massive amount of the nation’s history happened right here in Boston, which was originally called Trimountaine.
  • Salem. The town most known for its witch trials was also a crucial place for shipbuilding during the Revolutionary War.
  • Ipswitch. This town was founded in 1878 by John Winthrop the Younger and is home to the Crane Estate which was built in 1910. 
  • Watertown. This town has one of the first woolen mills in the country which was built in 1662 as well as the first grist mill in New England.

Discover more about the most historical towns in Massachusetts

What are the smallest towns in Massachusetts?

The smallest towns in Massachusetts include:

  • Tyringham. This tiny village’s name came from Norse roots which became Olde English and it means the Home of Tyr. 
  • Gosnold. With only 75 people, this is certainly the tiniest town in the state and its town hall is literally a house. 
  • Savoy. This was originally called New Seconk when it was settled in 1777 and it has a population of 692 people.
  • Middlefield. This town of 521 people got its start in 1783 and it is full of bucolic beauty and New England charm.

Find out more about the smallest towns in Massachusetts

What are the most charming small towns in Massachusetts?

The most charming small towns in Massachusetts include:

  • Newburyport. This quaint town is great for antiquing and strolling. Locals and visitors love the Market Square area.
  • Rowe. This is an extremely tiny town of fewer than 400 people and people flock here to enjoy Pelham Lake.
  • Hadley. This town is comprised mostly of open-field farms which are otherwise mostly now absent in the state.
  • Rockport. This coastal town is pure New England charm and has a house that was built out of newspaper called The Paper House.

Learn more about the most charming small towns in Massachusetts