Football Showcases Bring 100+ College Coaches to Campus
Annual Recruiting Days highlight opportunities for student-athletes More than 100 coaches and recruiters from top-tier colleges and universities converged this spring on Simosa Field to scout our student-athletes, one of the many opportunities Cheshire Academy creates for those hoping to play in the future. The sessions also provide students a chance to discover the many […]
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 […]
