Student Life

The Cheshire Academy experience is full and active; living and learning takes place not only in the classroom, but also in the art studios, dormitories, dining commons, on the athletic fields, and even on the footpaths that wind around campus. The Academy is a tight-knit and dynamic environment that offers a community rich in diversity. Fellow students become friends, teammates, and confidants that often develop into decade-long friendships.

Teachers remain close by and ready to lend a helping hand, both in and out of the classroom. Faculty members accompany students on weekend events and activities. They drive the vans into town, host ‘Fire-pit Fridays’ complete with s’mores during athletic contests on the turf field, and open their homes to students for special dinner events.

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  • Community Dinners

    Cheshire Academy hosts Community Dinners that take place once a month and bring together the entire school to share in a meal, activity, and learning experience. 

    Community Dinners happen Tuesday nights, typically once a month. During these gatherings, students and faculty sit at assigned tables that help them get to know peers and faculty whom they might not see often. Each dinner is a new group and a new chance to get to know all members of the community.
  • Community Weekends

    Each Community Weekend has a theme, allowing the community to address important issues, take part in educational experiences and fun activities. Past themes have included Community Service, Anti-Bullying, Cultural Diversity, Arts, Leadership and Earth Stewardship.
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  • Weekend Activities

    While the Community Weekends are closed weekends, meaning everyone must remain on campus, we do have an open policy for most of the other weekends. That means students may go home or visit friends if they choose, but most students remain on campus.

    Every weekend, faculty members host trips to local attractions including shopping centers, cinemas, museums, restaurants and other great attractions. Sign up for activities like shopping at an outlet, paintball adventures, excursions to local beaches and dinners out in nearby towns. We even head to Six Flags Amusement park when the weather is nice!

    Feel like staying here? We have plenty to do. Join us for “Fire-pit Friday” at one of the turf games at Simosa Field where we roast marshmallows and make s’mores, or grab your swimsuit and jump in the pool for a screening of the movie “Jaws.” Gather your friends and check out Richardson Lecture Hall for the Friday Night Movie complete with popcorn and candy, visit friends during open dorm hours, or head to the regularly open spots on campus, including the gym, weight room and campus center. Activities offered vary by weekend, and suggestions for both on- and off-campus excursions are welcome!

Recent Community Events

Community Life Office

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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 
DEVELOPMENT OFFICE: 203-439-7307
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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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