Cheshire Academy is a selective, co-educational college preparatory school located in Cheshire, Connecticut, United States. Founded in 1794 as the Episcopal Academy of Connecticut, it is the eleventh oldest boarding school in the United States. In 1917, the school was renamed The Roxbury School, and trained young men exclusively for the purpose of attending nearby Yale University. Later known as Cheshire Academy, the school was the first private academic institution to accept international students dating back to the 1850s, and as of 2011 it is the only independent school to offer the International Baccalaureate Diploma Programme in the state of Connecticut.

Cheshire, formerly known as New Cheshire Parish, is a town in New Haven County, Connecticut, United States. At the time of the 2020 census, the population of Cheshire was 28,733. The town is part of the Naugatuck Valley Planning Region. The center of population of Connecticut is located in Cheshire.