Founded in 1794 as the Episcopal Academy of Connecticut, it is the eleventh oldest boarding school in the United States.

[6] Over the summer before the 2022-2023 school year, Cheshire Academy constructed new tennis courts and playing fields on their campus.

John Bowden, the school became renowned not only for training young men for the clergy, but also for educating students in the fields of English, Latin and Greek, philosophy, mathematics, and the sciences taught by leading colleges in the country at the time.

For this reason, many young women were sent to attend the school from distant townships in order to take advantage of such a unique educational opportunity.

The Roxbury School operated with the sole purpose of training young men to enter Yale University.

The class is designed to develop an artist’s passion in their chosen medium while providing a personal studio space to create their portfolios.

[20][21] The Town Scholar Program, established in 1937, provides a full, four-year scholarship to a resident of Cheshire entering the ninth grade.