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Lanesborough is situated just north of Pittsfield on Routes 7 and 8. Originally a farming community and one of the first settlements in Berkshire county, it was incorporated in 1765. In the 19 century, marble quarries opened and iron was discovered, marking an industrial chapter in the town’s history. Lanesborough is now a small residential community with a few farms, small businesses, several restaurants and pubs, and a Target store. Recreational areas are Pontoosuc Lake, which is surrounded by primary residences and vacation homes, the Ashuwillticook Rail Trail, Balance Rock State Park, Brodie Mountain and its Ramblewild outdoor recreation center, and Mount Greylock, the highest peak in Massachusetts. The town’s most famous native son was humorist Henry Wheeler Shaw, aka Josh Billings, celebrated in Berkshire County’s Josh Billings RunAground, which takes place annually in September and is one of the nation’s longest-lived triathlons.


In the northwest corner of the Commonwealth, at the Vermont border, Williamstown is a vibrant, college town, possessing lovely streetscapes, rural scenery, and myriad cultural, culinary, and outdoor attractions. Among these are the Williams College Museum of Art, the Sterling and Francine Clark Art Institute with its stunning wing by Tadao Ando, and the Tony Award-winning Williamstown Theatre Festival, a summer magnet for nationally and internationally known talent. For recreation, there’s the Appalachian Trail, Pine Cobble, and Mount Greylock State Reservation. The town, first settled in 1749 and incorporated in 1765, was named for Colonel Ephraim Williams, scion of one of the original Stockbridge families; he endowed a free school, which became Williams College in 1793. In the 19th century, the Green and Hoosic rivers and streams powered a thriving mill industry: today, Williams College is the town’s largest employer. Early agricultural traditions are preserved in Williams College’s experimental Mount Hope Farm, Cricket Creek Farm, Caretaker Farm’s CSA shares, and in its bucolic landscapes. The Williams College Athletic Center offers community memberships. It’s a short hop over the border to southern Vermont and the Bennington airport, which accommodates small planes.