Cheshire Academy is a 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.

The Academy enrolls about 360 students from approximately 31 countries and 19 states in grades 9 through 12 plus a postgraduate year.