Cheshire Academy Appoints Melissa Terrio as Inaugural Dean of Enrollment ManagementÂ
Historic New England Boarding School Marks Strategic Milestone with Senior Leadership Appointment Cheshire Academy is proud to announce the appointment of Melissa T. Terrio, M.Ed., as its inaugural dean of enrollment management, effective May 1, 2026. This newly created senior leadership position represents a defining moment in the school’s evolution. Founded in 1794, Cheshire Academy […]
Cheshire Academy Launches Next Chapter of Roxbury Program
Combining 25 Years of Legacy with Cutting-Edge Brain Science-Backed Pathways CHESHIRE, Conn. — Jan. 5, 2026 — Cheshire Academy today announced the next evolution of one of its most distinctive academic pillars: the newly rebranded Roxbury Center for Learning & Leadership, a comprehensive, neuroscience-driven program designed to help every student reach their fullest potential. A signature program unique […]
NBC Features Cheshire Academy 12th Grader for Offering Free Tennis Clinic in Jamaica
Chase Harding combines athletic excellence with service, embodying Cheshire Academy’s mission of “Individual Growth. Global Purpose.” When Chase Harding returned to his hometown of Kingston, Jamaica this summer, he didn’t just visit — he created opportunity. The Cheshire Academy 12th grader brought donated rackets and equipment to the neighborhood of Payne Land, where he hosted […]
Cheshire Academy Academic Dean Shares Grading Insights on National Podcast
Rewarding collaboration, character, and mastery is key at Cheshire Academy In a November episode of the podcast “The Brighter Side of Education,” Cheshire Academy Dean of Academics Marc Aronson imagined a school where grades reward collaboration, character, and genuine mastery—not just memorization and speed. He shared with teachers across the country how Cheshire Academy rethought assessment through Grading What Matters, a framework […]
Chicago Bears VP, Cheshire Academy Alum Returns to Inspire Football TeamÂ
Pat McCaskey ’68, corporate secretary and vice president of the Chicago Bears, came back to Cheshire Academy for Homecoming Weekend 2025, enjoying dinner with the football team and offering inspiring words before their victorious match-up against Brunswick School. “He had dinner with us in Bowden Hall, which is big for the kids because they see […]
‘Behind the Seams’ – How a Private School Costume Shop is Preparing Students for Life
Cheshire Academy teachers are lifelong learners and experts in their fields. We asked them to share their thoughts and scholarship on vital issues in education. Â Sara Kelleher is an instructor in the Roxbury Academic Support Program at Cheshire Academy. A teacher for a decade, she holds an M.Ed. from Johns Hopkins University School of […]
Cheshire Academy Opens 232nd School Year at ConvocationÂ
Heartfelt speeches and song mark annual ceremony on Simosa Field Cheshire Academy opened its 2025-26 academic year on Sept. 7 with a lively Convocation, featuring songs and speeches from students, advice from Head of School Tom Woelper P’26, and wise words from a longtime employee, parent, grandparent, and friend. The 232-year-old school, the 11th oldest […]
Why Should I Attend Private School? Â
Choosing between private and public high school can be nerve wracking. Here are a few things that set independent schools apart.    If you’re deciding whether to send your child to public or private high school–or if you yourself are looking, you may be asking yourself: What makes private school worth the investment? What benefits are […]
What Questions Should I Ask on a Private High School Tour?
You’ve checked out the website, read the brochures, and met an admission counselor during a school fair. Want to know what it’s really like to live and study at an independent school?  Visiting in person is the best way to find your child’s home away from home – especially if you take the time for […]
