Campus Life

Learning doesn’t take place only in the classroom—at Cheshire Academy, it happens everywhere, every day. In all locations and programs, students expand their horizons in a vibrant, full, and active setting; in the art studios, student center, dining commons, and dormitories, on the athletic field, and along the pathways of campus.


Our tight-knit and dynamic environment is rich in diversity. Our boarding, day, and international students become friends, teammates, and confidants who form lasting connections.


Here’s an example of a packed weekend: Weekend Schedule


Our faculty members living on or off campus lend a helping hand to students at all hours, during study hall, extra help sessions, and afternoon activities, and in the classroom. Weeknight and weekend activities include evening residential programming, trips into nearby towns and cities, community service opportunities, “Pillar Events” Community Weekends, special dinners, on-campus activities in the gyms, open library and Student Center hours, shopping trips, college tours, adventure excursions, and countless other exciting opportunities for exploring new experiences and forming friendships.

Wesley Simon

Dean of Community Life; English Teacher

203-439-7604 email: Wesley Simon MORE

Kristin Ornato-Giano

Student Activities/Athletic Events Coordinator

203-439-7445 email: Kristin Ornato-Giano MORE

Barbara Wrzosek

Community Life Assistant

203-439-7256 email: Barbara Wrzosek MORE