About CA

Signature Programs

Cheshire Academy students grow increasingly capable of independently observing, questioning, explaining, interpreting, and analyzing the world. Our academic process begins with what students know and want to know. Cheshire Academy develops active learners who reflect on their growth and the implications of their learning.

Campus Life

The Cheshire Academy experience is full and active; living and learning takes place not only in the classroom, but also in the art studios, dormitories, dining commons, on the athletic fields, and even on the footpaths that wind around our 226-year-old campus. On weekends, faculty and students continue to learn both on and off campus, with fun activities including visits to nearby colleges, universities, museums, libraries, and trips to nearby cities and different attractions throughout New England.

Roxbury Academic Support Program

Cheshire Academy is the only Connecticut private school to offer one-to-one student coaching through the Roxbury Academic Support Program, an optional, fee-based program that focuses on developing and enhancing students’ executive functioning, study, and self-advocacy skills, among other abilities necessary to help them become more productive learners. Students who take advantage of our Roxbury Academic Support often excel in IB program courses.

International Baccalaureate® Diploma Programme

For students in grades 11 and 12, the IB Programme aims to do more than other curricula by developing inquiring, knowledgeable, and caring young people who are motivated to succeed. We strive to develop students who will build a better world through intercultural understanding and respect. The Diploma Programme offers a rigorous course load for its students, one that challenges individuals to think critically and globally. U.S. colleges and universities may also recognize completion of IB courses for college credit. 

Art Major

Advanced art students in 12th grade interested in pursuing a career in the arts or majoring in art or design at the university level may enroll in the yearlong Art Major program course. The class is designed to develop an artist’s passion in their chosen medium while providing a personal studio space to create their portfolios.

Residential Life

5-day and 7-day boarding students live two to a room in one of five dormitories, each centrally located on campus. Some singles are available for upperclassmen. A full-service dining facility offers three meals on weekdays and brunch and dinner on weekends. Nearby restaurants and grocery stores are within walking distance. With full access to the fitness center, study areas, and student center, there is always something to do.


Cheshire Academy’s rich athletic history dates back to the 1800s. The Cats enjoy 18 sports for boys and girls. There are also non-competitive athletic activities to ensure all students have a healthy and physically active experience. Cheshire Academy has produced professional athletes as well as countless collegiate athletes. The Cats compete in the New England Preparatory School Athletic Conference. 

College Counseling

Students are supported at every step of the college application process, from discovering strengths to overcoming weaknesses, registering for standardized tests (SAT, ACT, and/or TOEFL), meeting with college representatives, visiting college campuses, writing application essays, completing applications, and submitting transcripts and recommendations to selected colleges. We ensure each student’s college process to be a rewarding and positive experience.

ESL/ELL Support

Students who speak English as a second language receive additional support in grammar, writing, pronunciation, and American culture.





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The Admission Office continues to accept applications for the 2022-23 school year.


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