Resources and updates for the 2023-2024 school year are available here




History, Mission & Values

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 both Boston and New York. CA takes a flexible and tailored approach, so students can 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 36 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 27 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 unique Art Major and Music Major programs for those who plan to continue on to an arts or music 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.


Cheshire Academy is an internationally minded college-preparatory school that challenges its students to maximize their potential by developing the confidence, character, and critical thinking skills that enable them to thrive as global citizens.

Pillars of Bowden

Character development has long been a priority at Cheshire Academy. The Eight Pillars of Bowden are the ways in which we demonstrate our core values and basic beliefs, and are represented by the eight pillars that support Bowden Hall. The structure was originally built in 1796 and is one of the oldest schoolhouses still in use. 

Respect • Responsibility • Caring • Civility • Citizenship • Morality • Fairness • Trustworthiness



We welcome and celebrate diversity, and we create an environment where everyone feels respected and valued for who they are. We seek to understand and share the feelings of others, and we show compassion and kindness to others.


We are present. Engaging with our community helps us to feel connected to our school and to each other. When we are engaged, we are more likely to thrive academically, socially, and emotionally.


We are honest and reliable, and we build relationships based on mutual respect and confidence. We work together as a team, and we leverage each other’s strengths and perspectives to achieve common goals. We hold each other accountable.


We are always learning and improving, and we seek feedback and opportunities to develop ourselves and others.
Cheshire Academy received an A+ rating on Niche.com

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