Chesterfield is a rural hill town in Hampshire County, Massachusetts, United States, 26 miles (42 km) east of Pittsfield and 90 miles (140 km) west of Boston. The population was 1,186 at the 2020 census. It is part of the Springfield, Massachusetts Metropolitan Statistical Area.

Hampshire County is a historical and judicial county located in the U.S. state of Massachusetts. As of the 2020 census, the population was 162,308. Its most populous municipality is Amherst, its largest town in terms of landmass is Belchertown, and its traditional county seat is Northampton. The county is named after the county Hampshire, in England. Hampshire County is part of the Springfield, MA Metropolitan Statistical Area. Together with Hampden County, Hampshire County municipalities belong to the Pioneer Valley Planning Commission.