How to Apply

We are thrilled that you are applying to Cheshire Academy! Below you will find a helpful outline of the steps necessary to complete your application:

  1. Complete our online application – set up an account, set your password, and begin your applications!
    This will include an essay and several short answer questions
    (We also accept the SAO, TABS, and Gateway to Prep School applications linked below) 
  2. Schedule a campus visit with interview or a Skype interview 

  3. Collect three recommendations
    1. Recommendation letter from a math teacher
    2. Recommendation letter from an English teacher
    3. Recommendation letter from the principal 

  4. If you’re applying for Grades 9 or 10 you should
    1. Provide Transcripts for current and previous school year
    2. Provide SSAT scores

  5. If you’re applying for Grades 11, 12, or PG you should
    1. Provide Transcripts for all years completed at the high school level
    2. Provide PSAT or SAT scores
  1. If English is not your native language, you may submit a TOEFL or IELTS or Cambridge English exam in lieu of the SSAT
  1. If you are requesting our Roxbury Support program or other accommodations, please include all educational testing.
The application deadline is February 10th. We send out admissions notifications on March 10th and families have until April 10th to enroll. Decisions are made on a rolling admission basis for any student who applies after March 10. Please call 203-439-7250 or email regarding availability after February 10th.


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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