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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The town of Lanesborough is near the western edge of Massachusetts. The Taconic Range divides the town from Hancock on the west, and a spur of the Hoosac Mountains separates it from Cheshire on the north and east. These two ranges unite at the northern boundary at the foot of Mount Greylock, the highest mountain in the state; and the south opens out to an extended and beautiful view down the valley to Pittsfield and the mountains beyond. Pontoosuc Lake, one of the most popular recreation areas in Berkshire County, is on the town's southern border.
Lanesborough, in Berkshire County, is 140 miles west of Boston; 37 miles east of Albany, New York, and 152 miles from New York City. It is a quiet, residential township comprised of around 3,000 persons living in two villages: Lanesborough Village and Berkshire Village, plus spread over the rural landscape. People come here to live and educate their children, but the majority earn their living in the neighboring towns and cities.