A staple of the private school experience at Cheshire Academy is an advisory system. All students are assigned to small groups of 5-7 students that are led by faculty members. Advisors  help guide students through their years at the Academy. Formal meeting times happen once a week, but most students see their advisors daily, sometimes just for a quick hello in the dining hall, passing between classes or in dorms. During advisor meetings, whether a formal group meeting or informal one-on-one meeting, advisors will discuss academics, athletics, social life and other issues relating to school life and life as a teenager in general.

Advisors are there to support their students when they need it, serving as mentors, advocates, counselors and support for their advisees, and are available to meet with students outside of formal advisee meetings. Advisors are an active part of student life, keeping track of academic performance, athletic and artistic endeavors, and general well-being. Sometimes, advisors provide guidance and then step back and watch the students learn and succeed on their own, while still checking in regularly. Other times, advisors take a more hands-on approach, giving more personal attention to the students who need and want it. This flexibility in working relationships is part of the student-centered experience, giving students the support they need when they need it.

Academic Office

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Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSIONS OFFICE: 203-439-7290
ADMISSIONS FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 
DEVELOPMENT OFFICE: 203-439-7307
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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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