Why Cheshire?

High school is so much more than just the next step on the path of doing what’s expected.

At Cheshire Academy, we don’t believe that education is about trying to fit some stereotype of an ideal student. We put the unique needs of every student first. That’s why we offer a flexible program that allows students to mix and match academic course tracks with athletic 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 fencing, volleyball, and ropes course challenges.

We are the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program, and students who take advantage of our Roxbury Academic Support often excel in IB program courses.

Cheshire Academy is also home to award-winning athletic teams such as basketball, football, swimming, volleyball, and softball. We have helped hundreds of students graduate and go on to play their primary sport at the college level.

Read our viewbook to find out more.

I Never Thought I'd ...


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

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

About Cheshire Academy

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  • The student-centered private school in CT

    Cheshire Academy is a boarding school in Connecticut that challenges students in grades 9-12 and Post Grad to discover and hone their unique talents. This college preparatory school offers personalized learning opportunities like the Roxbury Academic Support Program and the IB Program. Artists can benefit from the Art Major program, while high school athletes can benefit from competitive athletics. Overall, students at the private school are encouraged to become culturally sensitive and internationally minded, and develop the critical thinking skills, confidence, and character that enable them to succeed in college and as citizens of a global society. 
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