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 […]
CT Media Giant Taps Cheshire Academy Experts for Education InsightsÂ
Hearst Media “Education Outlook” Section Showcases Cheshire Academy Experts Hearst Connecticut Media turned to Cheshire Academy for expert insights for its quarterly education outlook section that ran in 10 state publications. The section, focused on school libraries, included a cover story, “School Libraries: Offering Resources, Source Knowledge, Respite & Much to Read,” featuring comments from Director of Library Services Kate Daly ’05. In the current world, Daly said, a […]
Cheshire Academy to Launch Apogee Fencing Program
Elite program pairs world-class coaching with rigorous IB academics at historic Connecticut boarding school CHESHIRE, Conn. — Jan. 14, 2026 — Cheshire Academy today announced the launch of Apogee Fencing at Cheshire Academy, an elite competitive program offering promising international fencers the opportunity to compete at the highest levels of the sport while earning their […]
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 Announces 2026 Online Summer Program for Students Entering Grades 7-12
Inquiries now accepted, registration opens Jan. 5 INQUIRE NOW CHESHIRE, CT – Cheshire Academy is pleased to announce Summer at Cheshire Academy 2026, a five-week online learning experience designed to help students get ahead, stay sharp, and prepare for academic success. Running from July 13 through August 14, 2026, this program offers live, engaging courses […]
Cheshire Academy Gets an A+ in 2026 Niche RankingsÂ
The Academy receives high marks for diversity, activities, college prep in national survey Cheshire Academy received an overall grade of A+ in the 2026 Niche ratings of high schools across the nation, ranking #159 in the Best Boarding High Schools in America category. The independent boarding and day school also ranked in the top 5 […]
EXPLO Elevate Publishes Expertise from Head of School Tom WoelperÂ
Cheshire Academy’s Head of School, Tom Woelper, shared his insights on the future of education in “Lessons from the Startup Frontier: Transforming Traditional Education,” an essay published by EXPLO Elevate, a national organization that partners with schools on strategic planning, governance, and leadership. Woelper’s expansive essay touches on the history of American independent schools and what’s […]
New Cats on the BlockÂ
Students, families picture themselves in blue and white at Accepted Students Day Dozens of prospective Cheshire Cats converged on campus on April 1 and 4, enjoying pep rallies, a faculty-student basketball game, activities fairs, mock classes, and a chance to talk to current students and parents about their experiences.  Events began with a welcome in […]
Cheshire Academy Announces 2025 Town ScholarÂ
CA “party bus” delivers with a four-year scholarship for Ava Dasilva Cheshire resident Ava Dasilva probably wondered why her parents had such a long list of chores for her to do around the house on March 6. She got her answer at 10 a.m. when Director of Admission Rebecca Brooks drove the Cheshire Academy “party […]
Unlocking Potential: 25 Years of Roxbury Academic Support
Becca Yimlamai ’25 has a lot on her plate. Part of both the Asian Student Union and the Jewish Student Union, she is a member of Eco Leaders and a student leader of The Coleman Group, a campus mentorship club that aims to empower young women. She was elected as treasurer of the National Honor […]
