On Campus Events

Cheshire Academy boasts a beautiful, 104-acre campus less than a half hour from New Haven (home of Yale University) and an hour and a half from New York City. We encourage families to visit our historic campus for Admission events which include open houses, in-classroom visits, and discussion panels with current students and faculty.

List of 4 events.

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On The Road Events

Admission Officers travel around the world to meet with students interested in applying to Cheshire Academy. Upcoming off-campus events, such as secondary school fairs, are listed below. If your town is not on the list, please contact us to arrange a visit to your area by an alumni representative or admission officer.

Admission Office

List of 8 members.


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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