Welcome from the Head of School

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. This year we are particularly excited to share our history with you as we celebrate our 225th birthday. As I remind our community, when we first opened our doors in 1794, George Washington served as President of the United States. We are proud to be the 10th oldest boarding school in the country and have remained true to our mission throughout our amazing history.

Cheshire Academy has a longstanding tradition of embracing the tenets of a global education. We enroll students from a highly qualified applicant pool, creating a microcosm of a global society with students who come from more than twenty different states and over thirty-four countries. As an internationally-minded college preparatory school, we live our mission through offering the International Baccalaureate program in conjunction with the Roxbury Academic Support Program and a thriving curricular experience which 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 athletic play 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 what 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 you visit campus you will be struck by our warm, welcoming community of students from all over the world. Schedule your visit today and meet faculty, dorm parents, and coaches who are committed to supporting the academic and personal growth of each student on campus. I welcome the opportunity to extend my personal welcome to you. If you’re already a member of the community, make time to come back to campus for a personal visit or attend one of our many events. Keep us updated on your milestones in life through Class Notes and stay in touch with us; we welcome your stories and memories about life at Cheshire Academy.
I eagerly await the opportunity to get to know you and to share what I love about Cheshire Academy with you.


Julie Anderson
Head of School


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSION OFFICE: 203-439-7250
ADMISSION FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

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  • The Student-Centered Private School in Connecticut.

    We put the unique needs of every student first. That’s why we offer a flexible program that allows students to mix academic course tracks with athletics and/or fine arts programs, according to their needs and interests. Students can stretch their intellectual boundaries by taking one of 20 advanced International Baccalaureate® Diploma Programme courses, or practice new skills by participating in a range of afternoon programs including; athletics, fine arts, and performing arts. We are also the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program.
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