20. Great Barrington, Massachusetts
This quaint Massachusetts town brings visitors from all over the state as well as day-trippers from Connecticut, New York, Vermont, and New Hampshire. It’s also the birthplace of W.E.B. Du Bois, who helped found the NAACP.
The community sits under the beautiful gaze of the Berkshires and has a naturally warm and welcoming atmosphere with cute shops and boutiques lining its historic streets. One of the best features of Great Barrington is the availability of modestly priced real estate in a very friendly area of the state. Great Barrington is a destination for travelers far outside of Massachusetts, so its welcoming nature is known far and wide.
Real estate website Trulia suggests that the median sales price for homes in the first quarter of 2014 hovered around $265,700 and that most properties for sale or which sold in the area ranged from about $320,000 to $340,000.
Because of Great Barrington’s location on the western side of Massachusetts, the average temperatures enjoyed by residents are a little lower than those experienced by many of the best towns along the coast.
The Weather Channel’s data suggests average temperatures during the day in the low 30s during the winter, but the nights get particularly cold with lows that almost reach the single digits.
The town seems particularly committed to ensuring its residents lead a green lifestyle and has an extensive section on its official website detailing eco-friendly and earth-friendly procedures for energy, water use, and recycling.
Residents and visitors are also treated to some lovely outdoor opportunities with travel website Trip Advisor suggesting that hiking the Monument Mountain trail and visiting the Housatonic River Walk are two of the most enjoyable natural pursuits in the area.
Visitors may enjoy Great Barrington in the summer with the beautiful weather, or they may travel to the town in the winter for snow activities at Ski Butternut.