How to Harness the 3 A’s for Student Success in High School English
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. English Department Chair Jaimeson Lynch teaches IB® English Literature at Cheshire Academy, where she received the 2024 D. Robert Gardiner Excellence in Teaching Award. She is also an IB English A […]
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 […]
WTNH News 8 ‘Good Morning CT’ Interviews Cheshire Academy 12th-Grader on Yale Internship
Nia Jackson ’26 appeared recently on WTNH-TV, the ABC affiliate in New Haven, celebrating her summer spent in a prestigious Yale University medical internship for their ‘Good Morning Connecticut’ segment. Nia was one of just 19 students from across the country who won a spot in the Discovery to Cure program, an internship in women’s reproductive […]
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, […]
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 […]
How Language Drives Purpose: Refreshing Cheshire Academy’s Mission
In the age of AI, you’d think refreshing an independent school’s mission statement would be as easy as typing a few key words into a text box and hitting “Go!” But, at Cheshire Academy, our mission – both the goals and aspirations behind it and the words that form it – is carefully considered. So, […]