Welcome home!

Whether you are an incoming first-year student, a parent ready to enroll your accepted student, or a new student joining us from another country, we are excited to help you through the enrollment process in a few easy steps.

  1. Make your enrollment deposit online by clicking here
  2. Submit your enrollment contract to the admission office
  3. Log in to MyCheshire: Parents and students will receive an email within two weeks of submitting the enrollment deposit with their MyCheshire credentials. Please locate this email and make sure to use the correct information to log into MyCheshire. If you are having trouble logging into MyCheshire or locating the email, please contact Caitlin Garzi.

MyCheshire Resource Board

As part of the Cheshire Academy community, you can expect to receive all important information from school officials and teachers through MyCheshire, our password-protected website affectionately known as "The Portal." 

Each parent or guardian will have their own login information, as will each student. You can expect to receive your username and password within two weeks of submitting your enrollment deposit.
Days Until Registration Day!


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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