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, […]
11 New Faculty and Staff Members Join the CA Team
Each brings a wealth of experience and talent to the community Cheshire Academy welcomed 11 new faculty and staff members for the 2025-26 academic year, including two CA alums. The cohort includes new faces in the classrooms, as well as the Roxbury Academic Support program, athletic training, and the health and counseling departments. “We are […]
AJ Soldra ’23 drafted by the L.A. Dodgers
Soldra is the first Cheshire Academy alum to be drafted to Major League Baseball. AJ Soldra ’23, a former post-graduate outfielder at Cheshire Academy, was chosen by the Los Angeles Dodgers in the 16th round of the 2025 Major League Baseball draft. Cats Head Baseball Coach Anthony Giano P’19,’20,’23 certainly isn’t surprised. “He had tremendous […]
How to use AI in the Classroom: A Guide
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. George Aiello is academic technology coordinator and librarian at Cheshire Academy, having held similar positions in schools in Hong Kong, Paraguay, and Singapore. Before making the career change to education, […]
Former Cheshire Academy QB Reno Talks to NY Times on Yale Move
Quarterback Dante Reno ’24, who led the Cheshire Cats to a league championship in 2023, was interviewed by the New York Times about his decision to play football at Yale University, where his dad, Tony Reno, is head coach. The announcement made sports news across the country, with stories about the novel father-son arrangement in […]
