At Cheshire Academy, boarding students make up approximately 65% of the school community and come from 17 states and 30 countries. Living on campus helps students to learn and grow in a supportive and empowering community.

There are five single-gender dormitories on campus, all of which are home to several faculty members and their families. Additional faculty members live in campus housing scattered throughout the 104-acre campus. Although each dorm differs in design, all living quarters for students have a main lounge area with a television. The majority of rooms are designed for two students, though there are some single and triple rooms also available.  

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  • Abigail Zuckert ‘17

    Living across the hall from my best friend is just incredible. I love living on campus. - Abigail Zuckert ‘17
Attending a college preparatory school like Cheshire Academy is one of the best ways to prepare for life at college. Boarding school provides a safe environment for students to explore their independence and learn to take responsibility for their own lives. Living on campus provides students the structure and adult guidance they need to build self-reliance and maturity that will serve them well in college and beyond.

Dorms at Cheshire Academy are more than just a place to sleep and study. These residential homes are also a place to unwind, study, talk to friends, listen to music, play games and find time to be alone. Living together on campus helps students and faculty to bond and forge lifelong connections. Friendships built here continue long after graduation.


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

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  • 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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