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 […]
Remembering Cheshire Academy Trustee Emeritus David Jepson ’59
Beloved alum, former trustee, passed away Oct. 8, 2025 It is with heavy hearts that we share the passing of former trustee and true son of Cheshire Academy, David Jepson ’59. David was a graduate of Cheshire in 1959 receiving the Costin Cup, the award for the student who most improved while at the school. […]
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 […]
The Act of Courage and Kindness That Gave O’Connor House Its Name
Nearly all readers know the name David Markin. David’s name is attached to several major structures on campus. Few readers, however, know about his role in assigning the name “O’Connor” to our Head of School residence. David arrived at CA in 1947 at a time when, to their discredit, many schools did not admit Jewish students. […]
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 […]
World’s Best – Global Citizenship Pathway Provides More Ways to Personalize a Cheshire Education
Global Citizenship pathway, honors distinctions provide even more ways to personalize a Cheshire education In 2022, Cheshire Academy launched an ambitious new academic vision statement: “Cheshire Academy aims to provide the best (anywhere) education in global citizenship.” Since then, the school has worked to build on that vision’s four foundational concepts: teaching 21st-century skills and […]
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 […]
Cheshire Academy Opens 232nd School Year at Convocation
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 […]
