Admission Open House - Oct. 9 [Click Here](https://cheshireacademy.org/events/#REGISTER)
Admission Open House - Oct. 9 [Click Here](https://cheshireacademy.org/events/#REGISTER)
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About CA

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 365 students from 11 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 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 25 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.


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. Bowden Hall was originally built in 1796 and is one of the oldest schoolhouses still in use.


Cultivate “the ability to respond,” which is the action side of respect. If we respect people, we value them. If we value them, we respond to the needs of others and feel a measure of responsibility for their welfare.


Show you care about others through consideration, compassion, kindness, and sharing. Live by the Golden Rule. Help others. Be sensitive to others’ feelings. Be charitable and giving of yourself.


Behave courteously in everything you do. Express an appreciation for community values through appropriate behavior. Acknowledge the worth of others by acting respectfully and responsibly toward them.


Play by the rules. Obey laws. Do your share. Respect authority. Stay informed. Participate in your community. Protect those around you. Volunteer your service. Protect the environment by conserving natural resources.


Be aware of the fundamental values of good and bad. Acknowledge your conscience, self-control, empathy, and sense of humility. Make decisions based on positive values, not desires.


Treat all people fairly. Be open-minded. Listen to others and try to understand what they are saying and feeling. Make decisions that benefit everyone equally. Think win-win. Take only your fair share.


Tell the truth. Be sincere. Don’t deceive or mislead. Don’t betray a trust. In relationships of trust, share important information. Walk your talk by being your best self and by showing commitment, courage, and self-discipline.

Core Values


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.

Civil Discourse


As reflected in the Eight Pillars of Bowden, Cheshire Academy strives to foster citizenship and responsibility among students by encouraging curiosity for and participation in the political process. We believe that the capacity to listen to others with opposing viewpoints builds empathy, understanding, and awareness. With this in mind, we encourage engagement in conversations where diverse viewpoints can be shared—also known as civil discourse.


Statement on Civil Discourse (PDF)