At a Glance



Day and Boarding


Grade 9–12 plus PG


362 students






104 acres (.42 km2)


Halfway between Boston and
New York, but walking distance from local establishments.


Bradley International Airport (Hartford)
is a 30-minute drive, while New York City and Boston airports are 2 hours away.


Cheshire has four seasons:
warm summers, beautiful autumns, flowery springs, and frosty winters.


French, Mandarin, and Spanish.


119 courses
32 IB courses


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 and develops active learners who reflect on their growth and the implications of their learning.

International Baccalaureate® Diploma Programme:
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.

Roxbury Academic Support:
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.

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.

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

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 the 224-year-old campus.

Residential Life:
Students live two to a room in one of five dormitories, each centrally located on campus. A full-service dining facility offers 3 meals a day, while 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 have a combined over 20 sports for boys and girls. There are also non-competitive athletic activities to ensure all students have an enjoyable and physically active experience. Cheshire Academy has produced professional athletes as well as countless collegiate athletes.

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.

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Address: 890 Lorem Ipsum Street #12 San Francisco, California 65432 Phone: 123.4567.890 Business Hours: 8a-6:30p M-F, 9a-2p S-S