Resources and updates for the 2024-2025 school year are available here


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.

Community Dinners

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

Every weekend, faculty members host trips to local attractions, including shopping centers, cinemas, museums, restaurants, and other great attractions. Students may also sign up for (and request) a variety of activities, such as escape rooms, paintball, excursions to local beaches, community service opportunities, and college campus tours. We even head to Six Flags New England amusement park when the weather is nice. Activities offered vary by weekend, and suggestions for both on and off campus excursions are encouraged!

Faculty Members Lend a Hand

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.

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