Cheshire is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. The population was 3,401 at the 2000 census.
Cheshire was first settled in 1766 and was officially incorporated in 1793. It is named for Cheshire, England.
The valley town was founded by Baptists from Rhode Island, the first settlers in the region who were not of the established Puritan Church. The early colonists were mostly descendants of those who had followed Roger Williams to Rhode Island in their quest for religious freedom. One of the prime movers of the emigration was Colonel Joab Stafford, who built his house on Stafford Hill and led the men of Cheshire into war during the Revolution. The troops from Cheshire distinguished themselves at the Battle of Bennington.