How to Apply

Once you have completed your pre-application Inquiry Form, the Admission Office will email you with a username and password so that you can start and save your application to the Academy through the MyCheshire Portal. If you have forgotten your username or password or are not sure if you already have one, please email

The following materials are necessary to complete your application:
  1. Online application, which includes an essay, short answer questions
  2. In-person or Skype interview (application does not have to be complete for interview)
  3. The SSAT is the preferred test for applicants, though ISEE, PSAT, or SAT scores may be submitted (depending on the grade you are applying for). Cheshire Academy offers on-site SSAT testing; click here to view dates and times.
Application Deadline: 
February 10 - Priority Deadline
March 10 - Notification Deadline
April 10 - Enrollment Deadline

International student applications require a TOEFL score (for students whose first language is not English). The Secondary School Admission Test is recommended, though not required, for international students. Upon enrollment at Cheshire Academy, the Admission Office will issue an I-20 so that international students can obtain student Visas in time for travel to the United States.

Scheduling an Interview: To arrange an interview, please contact the Admission Office at 203-439-7250 or


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

List of 1 items.

  • 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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