Cheshire Academy’s track and field program is one of the largest afternoon activities on campus and each student-athlete can choose his or her events. The Cats have a full varsity schedule for the boys’ and girls’ teams competing against other prep schools. The season culminates with the New England Preparatory School Athletic Council (NEPSAC) Division III Championships in May.

Many student-athletes have gone on to compete collegiately, most notably Alexis Holmes ’18. Holmes, who now runs at the University of Kentucky, became the Cats’ first Division I female track athlete. She was part of the United States’ 4×400 relay team that set a World U20 record at the Pan-Am Games in 2019.

Highlights of the track program include Penn Relay titles in 1963 and 1964, along with boys New England Division III titles in 2007 and 2016. The girls won the New England Division III title in 2009. Cheshire Academy’s home meets take place on the newly renovated Simosa Field & Track.