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.

Collection comprises deeds (land and pew) in Nathaniel Chickering's name and an account booklet of Mrs. Otis Chickering. Nathaniel Chickering's deeds show evidence of mills in Belchertown, Massachusetts in 1813 and Enfield in 1835. He seems to have been on the line between the two towns and may have owned property in both at the same time. In 1843, Nathaniel Chickering bought a horse shed near the church in Enfield. Mrs. Otis Chickering's account booklet consists of six pages of her accounts with C.F. Wood and Co, from the years 1856-1873.