Cheshire Academy Announces 2026 Online Summer Program for Students Entering Grades 7-12
Inquiries now accepted, registration opens Jan. 15 INQUIRE NOW CHESHIRE, CT – Cheshire Academy is pleased to announce Summer at Cheshire Academy 2026, a six-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 via […]
Chicago Bears VP, Cheshire Academy Alum Returns to Inspire Football Team
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 […]
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. 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 Gets an A+ in 2026 Niche Rankings
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 […]
Never Give Up, Never Grow Up: Alum’s Journey from Cheshire Cat to Furby
Richard C. Levy ’64 Many students come to Cheshire because of its academic reputation, top-notch college counseling, or chance to catch the eye of NCAA Division I university coaches. For Richard C. Levy ’64, it was all about the jacket. While touring Cheshire Academy, he took one look at the school’s navy wool classic emblazoned […]
Caring Alum Makes a Difference at Ann Hewan Foundation
Exposure to international issues at Cheshire opened a whole new world for one caring alum Others might look at the forlorn field behind Goodwill School in Montego Bay, Jamaica, and see uneven ground, rubble, and the odd tree stump. Jaida Williams ’19 sees opportunity. By creating a soccer field behind the school Williams’ parents attended, […]
Dean of Academics Discusses ‘Grading What Matters’ on Education Podcast
Marc Aronson enters timely discussion of how grading measures learning, motivates students Cheshire Academy’s Dean of Academics Marc Aronson appeared on “The Grading Podcast,” a national podcast reimagining grading as a tool for student success. “The liberation that can be gained from throwing away the percentage-based scale as a mindset I think is something that […]
Cheshire Academy 12th-Grader Makes Career Discoveries at Yale Summer Research Program
A Venture Grant Adventure More than 200 high school students from across the country applied for the prestigious Discovery to Cure Internship in women’s reproductive cancers at Yale University this summer. Nia Jackson ’26 was one of just 19 who earned a coveted spot in the program, getting a taste of life as a lab […]
Above & Beyond: Life-changing Moments that Come with a Cheshire Academy Education
A book re-publication, masterclasses, and conference presentations illustrate the ‘life-changing’ moments that come with a Cheshire Academy education The cacophony in the van heading from Emily Dickinson’s Massachusetts home back to campus would have been enough to make the famously reserved Belle of Amherst blush. Four girls threw their heads back in unison. “Wind in […]