My Cheshire
A note from the Admission Team - Thank you for visiting the Cheshire Academy Admission page and for considering us in your search for your next school! Our Admission Team is here to guide you through every step of this exciting process and we hope that you will contact us with any questions you may have.

Have you ever imagined going to a school steeped in a rich history (founded in 1794!) but also on the cutting edge of educational and social innovation providing our students with 21st Century skills and global experiences? How about a school that meets you where you are on your learning journey and helps you get to exactly where you would like to be by providing support when you need it and independence when you want it? How about a school with small and individualized classes and classrooms where discussions and questions are encouraged (and one of the only boarding/day schools in New England with the academically challenging, but inclusive to all types of learners, International Baccalaureate Program)?Do you think it would be exciting to go to school with students from all over the United States and from many corners of the globe (28 countries to be exact!) and celebrate the vibrant and global society we live in through activities, classes, and just getting to know people from places other than where you have grown up? What about playing sports on many different levels of athletic teams or participating in our extensive art program which will support your growth, challenge you, and maybe even help you find a passion or talent that you didn’t know you had? Finally, would you like to go to school on a sprawling 104 acre campus right in the middle of a vibrant, safe, and friendly main street town only about 2 hours from New York City and Boston?

If you answered yes to any or all of these questions we hope that you will schedule a visit to see for yourself what makes Cheshire Academy so unique among other day and boarding schools out there. We promise your visit will be full of laughter, learning, and friendly interactions! We look forward to meeting you soon and helping you to imagine yourself here! 

In this section of the website, you’ll find more information about applying to Cheshire. You can also contact our Admission Office at 203-439-7250 or You can also visit our Admission blog. We’re waiting to meet you!

Admission Events & Travel
12th Annual Secondary School Fair
6:00 PM to 7:30 PM
Location: The Country School, Madison, CT
Contact: Kristen Mariotti

WCBS Admission Consultants Tour
1:45 PM to 4:00 PM
Location: Blue Room
Contact: Kristen Marriotti

JBSA & WCBS School Fairs
6:30 PM to 8:30 PM
Location: The House of the Redeemer, New York, NY
Contact: Kristen Mariotti
More Events
What Will Your Journey Look Like?