Cheshire Academy

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, CT, just two hours from both Boston and New York. With approximately 344 students from 19 states and 31 countries, the Academy 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 32 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, 10 non-competitive offerings, many performing and visual arts options, there’s a passion to be uncovered for all students. The Academy 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 trained learning specialists create 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 a community in which talented, dedicated faculty and staff motivate our students to stretch beyond their comfort zone. We encourage our learners to embrace academic rigor, challenge themselves in their course load, and to try new activities to broaden their perspective. Developing citizens of strong character is at the heart of what we do and is based upon the Eight Pillars of Bowden: respect, responsibility, caring, citizenship, civility, morality, fairness and trustworthiness.

As an internationally minded college-preparatory school, we live our mission through offering the International Baccalaureate® Programme in conjunction with the Roxbury Academic Support Program, and a thriving curricular experience that includes the Art Major program with robust visual and performing arts courses. We strive to instill confidence in our students and provide for them opportunities to collaborate and think critically.

Our students’ success in academics is complemented by strong performances in athletics, music, theater, and visual arts. We are committed to supporting both the interests and talents of our students which is evident in the multitude of options offered in our afternoon program. From high-level varsity athletics to theater and musical performances as well as Science Olympiad, Model UN, and community service, there is something for everyone at the Academy!

The truth is, our students’ interests are as diverse and unique as they are, and it is our mission at Cheshire Academy to meet our students where they are and take them beyond where they imagined possible. We accomplish this with the fine work of our outstanding faculty, supportive and rigorous academics, immersive afternoon programs, and vibrant residential life experience.

When the global situation has stabilized and you are able to visit campus, you will be struck by our warm, welcoming community of students from all over the world. Our campus is closed to visitors right now; however, we are hopeful that we can welcome you in the fall so you can meet faculty, staff, dorm parents, and coaches who are committed to supporting the academic and personal growth of each student on campus. In the meantime, we would love to connect with you online. Contact our Admission Office today to set up a video call with an Admission Officer. If you wish, they can connect you with other members of our community so that you can truly get to know us from afar.