Nathaniel Chickering came to Enfield, Massachusetts in 1800 with his son Otis and operated a grist mill for twenty years. One of Otis' children, Bertrand, operated the Enfield telephone system in the Howe family store and lived with the Edwin H. Howe family.

Enfield was among the Western Massachusetts towns abolished in 1938 to allow the Swift River Valley to be flooded, thereby creating the Quabbin Reservoir to provide Boston with water.