Lindsay Shaw ’01 Tumbles into a Life of Sports and Scholarship
There are moments in the lives of many high school students when a mentor offers something that ends up changing the course of their young life. Such was the case for Lindsay Shaw ’01 when Head of School Dr. Jerry Larson gave her a book on sport psychology. Lindsay isn’t sure, but she thinks it […]
Cheshire Academy to Launch Apogee Fencing Program
Elite program pairs world-class coaching with rigorous IB academics at historic Connecticut boarding school CHESHIRE, Conn. — Jan. 14, 2026 — Cheshire Academy today announced the launch of Apogee Fencing at Cheshire Academy, an elite competitive program offering promising international fencers the opportunity to compete at the highest levels of the sport while earning their […]
‘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. Â 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 RankingsÂ
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 […]
Building a Reading List That’s Both Rigorous and Relevant
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 […]
Why Should I Attend Private School? Â
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 […]
