Founded in 1794, Cheshire Academy is a college preparatory boarding and day school for students in grades 9-12 and postgraduate. Our historic 104 acre campus is located in Cheshire, Connecticut, just two hours from New York City and Boston and only 20 minutes from Yale University.
Cheshire Academy takes a flexible and tailored approach, allowing students to combine a variety of academic and extracurricular offerings optimal to their individual needs, strengths, and interests. As the 11th oldest boarding school, students join in a proud tradition of excellence, empowered by a close, caring community that challenges them, encourages them and supports them in every way. We help students to create their own path to success by recognizing their unique talents and potential.
Cheshire Academy offers the International Baccalaureate (IB) Diploma Programme, a challenging, global education curriculum that is recognized throughout the world. All students take IB courses in their 11th and 12th grade years and 35-50% of the 11th grade class is selected each year to participate in the full IB diploma program, the most rigorous academic path a student at Cheshire Academy can choose.
The Roxbury Academic Support program offers research-based practices for students to meet the demands of a secondary school education. Students work one-on-one with Master’s level learning specialists who offer executive functioning skill building and learning strategy instruction.
More than 70% of the student body participates on varsity and junior-varsity teams for 14 sports, including Fencing. Over 20% of graduates each year go on to play athletics in college, compared to a national average lower than 10%. More than 35% of students participate in the performing arts (visual arts, music and theater).