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 in 1765. It was renamed Lanesborough, for the Countess of Lanesborough, a friend of Governor Francis Bernard, who incorporated the town. The town grew with small industry in the early 19th century, most of which settled along Town Brook. Berkshire Pleasure Park was a major attraction at the turn of the 20th century. It was one of the trolley parks along what is now Route 8 on the eastern side of town.
Today the town includes many small businesses, but has little industry of its own. More people from Lanesborough are employed in nearby communities or at the nearby Berkshire Mall.
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.