In 1858, the town of Deerfield was sued by the Commonwealth of Massachusetts because it lacked a free school for secondary education. The trustees of Deerfield Academy, residents and leaders of the town, met and formed a free high school component of Deerfield Academy, with costs shared between it and the town.

This arrangement continued uneasily until 1875, when Esther (Harding) Dickinson (1790-1875) left the town $50,000 for construction of a public high school and library, which led to formation of a new joint academy and town school — Deerfield Academy and Dickinson High School. The new building opened on January 2, 1879. In 1917, the state demanded complete separation from private schools, a process that had to be completed by 1923. A buyout purchased the school from Deerfield Academy, and a new high school was then built using town funds.