Community 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 lifelong 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.

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 Sunday 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. Themes include: International Celebration, Diversity and Inclusion, Service to Your Community, and Fall Festival.

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, 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!

Wesley Simon

Dean of Community Life; English Teacher

203-439-7604 email: Wesley Simon PROFILE

Sara Griesbach

Dean of Residential Life

203-439-7613 email: Sara Griesbach PROFILE

Andrew McBreen

Associate Dean of Community Life; Math Teacher; Girls' Varsity Volleyball Head Coach

203-439-7207 email: Andrew McBreen PROFILE

Kristin Ornato-Giano

Student Activities/Athletic Events Coordinator

203-439-7445 email: Kristin Ornato-Giano

Owen Quantick

Residential Life Assistant

203-439-7480 email: Owen Quantick PROFILE

Barbara Wrzosek

Administrative Assistant

203-439-7256 email: Barbara Wrzosek PROFILE