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.

  • Sarah Thompson-Kablik 

    Acting Director of Admission & Director of Financial Aid
    Phone: (203) 439-7404
  • Nathan Sanders 

    Associate Director of Admission
    Phone: (203) 439-7239
  • John Toffey VI 

    Senior Associate Director of Admission, Director of Hockey and Head Coach of Varsity Baseball
    Phone: 203-439-7208
    Read Bio
  • Katherine Keogh 

    Admission Associate and Head Coach of Varsity Girls Soccer and Varsity Girls Lacrosse
    Phone: (203) 439-7621
  • Devin Worthington 

    Admissions Associate
    Phone: 203-439-7211
  • Jeffrey Allen Sr 

    Admission Associate and Girls Head Basketball Coach
  • Stacy Monico 

    Administrative Assistant to Admission Office
    Phone: 203-439-7290
    Read Bio


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

List of 1 items.

  • 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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