ATHLETICS
Playing for Cheshire sets student-athletes up for success — in college and beyond, both on and off the playing field. Our alumni have gone on to compete at some of the top universities in the nation, in the Olympics, and professionally.
70%
OF THE STUDENT BODY PARTICIPATE IN ATHLETICS
20+
ATHLETIC offerings
38%
OF RECENT CA GRADUATES WENT ON TO PLAY IN COLLEGE
About Cheshire Athletics
The Cheshire Academy athletics program offers 17 competitive sports programs for boys and girls, as well as a range of non-competitive athletic activities. At the Academy, students participate in a competitive team sport for two of the three seasons (fall, winter, spring) of every academic year as part of an afternoon program.
Athletics is an important priority because it encourages all students to take pride in contributing to something bigger than themselves. Students not only build new relationships with classmates, they also learn how to work as a team and support one another, they struggle and succeed together in new or higher-level challenges, and they continue to be lifelong learners through these afternoon activities.
Seasoned coaches with experience at the collegiate, semi-pro and pro levels lead many Cheshire Academy teams. In addition, coaches and assistant coaches are members of the faculty–athletes themselves–who are passionate about sports and the teams they lead.
Cheshire Academy has won more than 15 athletic championships over the last 10 years.
Cheshire Academy alumni have gone on to play at various colleges in recent years, including Brown University, Bucknell University, Colgate University, Columbia University, Dartmouth University, Fordham University, Harvard University, College of the Holy Cross, LaFayette University, University of Michigan, Princeton University, Stanford University, The University of Alabama, Worcester Polytechnic Institute, and Yale University.
At the professional level, our graduates have competed in the LPGA, NBA, NFL, and the Olympics.
Live Sports
You can find all of our livestreams in one convenient place through the hudl app on our YouTube channel! Just visit www.youtube.com/@CheshireAcademyTV/streams and make sure you are on the “live” tab. Watch basketball, football, lacrosse, soccer, or volleyball games on our page.
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Updates
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
NBC Features Cheshire Academy 12th Grader for Offering Free Tennis Clinic in Jamaica
Chase Harding combines athletic excellence with service, embodying Cheshire Academy’s mission of “Individual Growth. Global Purpose.” When Chase Harding returned to his hometown of Kingston,
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
