About CA

Signature Academic 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. Students who take advantage of our Roxbury Academic Support often excel in IB program courses.

International Baccalaureate® Diploma Programme

For 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.

Art Major

Advanced art students may take a year-long art major class. 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 17 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.



NEW: Updates about the start of the school year and resources related to COVID-19 can be found HERE.