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 […]
‘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 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 […]
Why Should I Attend Private School?
Choosing between private and public high school can be nerve wracking. Here are a few things that set independent schools apart. If you’re deciding whether to send your child to public or private high school–or if you yourself are looking, you may be asking yourself: What makes private school worth the investment? What benefits are […]
What Questions Should I Ask on a Private High School Tour?
You’ve checked out the website, read the brochures, and met an admission counselor during a school fair. Want to know what it’s really like to live and study at an independent school? Visiting in person is the best way to find your child’s home away from home – especially if you take the time for […]
