In a state with so much history, all around nature, and plenty of spots for a relaxing getaway throughout, it seems to be tough to not find a Massachusetts town would earn a spot among the most charming towns in America. So, what town in the Bay State checks all the boxes to end up as one of the five most charming towns in America?
When you think of Massachusetts, there's a good chance the first city, town, or region you would think of is Boston, Cape Cod, Salem, Cambridge, or Nantucket/Martha's Vineyard. Of course those are the usual popular destinations, and for good reason. There are definitely lots of other great spots throughout the state that I'm leaving out. But what about some of those other places around the Bay State that don't necessarily get the recognition. Those are the more underrated places around the state. It just so happens that the Berkshires is home to not one, but four of those spots.