One of the first Berkshire communities to be settled, Lanesborough was originally known as "New Framingham", carved from part of Northern Berkshire Township #6. Lanesborough was first settled in 1753 and was officially incorporated on January 21, 1765. It was renamed Lanesborough, for the Countess of Lanesborough, a friend of Governor Francis Bernard, who incorporated the town.
The town's most famous resident was Josh Billings, born Henry Wheeler Shaw. He was a popular humorist in the nineteenth century, rivaling Mark Twain for popularity at the time. Historic sites include the Old Stone School, an unusual stone one-room schoolhouse, built in 1832 from funds donated by Ephraim Bradley and which operated as a school until 1950. The building is currently used as a photography gallery and guesthouse.
Lanesborough is also the home of “King Elmer.” The tree dates back to the same year, or potentially older, as the town. The very large Massachusetts Champion Elm stands on Summer Street, visible from Route 7.
Lanesborough is situated in two valleys, with Town Brook running south through the central valley into Pontoosuc Lake, and the Cheshire Reservoir, the headwaters of the Hoosic River, running north through the town's smaller, eastern valley. To the north, the beginning of Mount Greylock is located in the town, with the auto road and visitors' center beginning there as well. Rockwell Road, which leads to the Visitors' Center, ascends from Lanesborough through Cheshire to the summit in Adams. Sperry Road, which branches off Rockwell, leads to a campground and picnic area. Pittsfield State Forest also has a large section within town, with Balance Rock being its main attraction. To the west, Jiminy Peak and Sheeps Heaven Mountain, the southern portion of Brodie Mountain, form much of the western border. While much of Jiminy Peak is located in the town of Hancock, recent aerial mapping determined that the summit is indeed in Lanesborough. The ski area's Hendricks Summit Lodge (named after Lanesborough residents Bart and Mary Hendricks) is located within the town. Lanesborough hosts the southern access to the Ashuwillticook Rail Trail, a bike path converted from a railway path.
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