The Power of the Postgraduate Experience: Christian Terrell ’13
One can only imagine how many great stories have arisen from Chesire Academy athletics over 232 years. Among other things, I wish we had more in writing about the post-Civil War period when just a few sports were played at CA. What were the games like then? With very few schools in existence in the area, where did we find teams to […]
Remembering Cheshire Academy Alum James Van Der Beek ’95
Class of 1995, Cheshire Town Scholar, 1977-2026 It is with profound sadness that Cheshire Academy mourns the passing of James Van Der Beek ’95, who died on February 11, 2026, following a courageous battle with colorectal cancer. He was 48 years old. James embodied everything the Cheshire Town Scholar award represents: scholarship, citizenship, ambition, and […]
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 […]
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 Reignites Community Tradition with Lights of Hope Event
Community invited to experience luminaries, support local charities on December 17 CHESHIRE, CT – Cheshire Academy is bringing back a cherished community tradition this December with the return of Lights of Hope, an evening event that celebrates service, unity, and the power of giving back. A Beloved Tradition Returns Inspired by the original Lights of Hope […]
Cheshire Academy’s Woelper in EdTech Digest: “The Case for Private High School in a Tech-Driven World”
Guest column offers thought leadership to readers around the globe Cheshire Academy Head of School Tom Woelper shared his insights on teaching responsible use of AI in “The Case for Private High School in a Tech-Driven World,” a guest column published in EdTech Digest. Woelper shared his timely thoughts on how independent schools are uniquely positioned to cultivate the judgment, creativity and self-direction needed as routine cognitive […]
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 […]
New Trustees Bring Business Acumen, Educational Expertise to Cheshire Academy
Joseph P’26, MacMullen, Svensk ’64 have joined the Cheshire Academy Board of Trustees, bringing a wealth of knowledge from the education and international business fields. The Cheshire Academy Board of Trustees has welcomed three new members – Priya Joseph P’26, William “Willy” MacMullen, and Robert E. Svensk ’64. They were elected during the Board’s May […]
‘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 […]
