Cheshire Academy

Founded in 1794, Cheshire Academy is a college preparatory boarding and day school for students in grades 9-12 and postgraduate. The historic 104-acre campus is nestled in the bucolic but central town of Cheshire, Connecticut, just two hours from Boston and from New York.

With approximately 304 students from 13 states and 21 countries, CA 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. For example, many students choose to stretch their intellectual boundaries by taking one of 32 advanced International Baccalaureate® Diploma Programme courses. This internationally respected program offers a global perspective, challenging students to be independent, critical thinkers concerned and involved with the world around them.

With 24 interscholastic athletic teams, non-competitive offerings, many performing and visual arts options, there’s a passion to be uncovered for all students. CA also offers a unique Art Major program for those who plan to continue on to an arts or design program at the university level.

Cheshire Academy recognizes that all students learn differently. Through our optional Roxbury Academic Support Program, our dedicated staff of masters-level instructors creates proactive, independent, competent learners by fostering tools and strategies to meet the rigors of a college preparatory environment and beyond. This proven approach yields thriving students who take responsibility for their academic success.