The cross country program competes in a series of dual meets and larger races in the fall. The races include the Choate Invitational, the Shaler Invitational at Williston Northampton and the New England Preparatory School Athletic Council (NEPSAC) Division III Championships.

The school’s signature event is the O’Connell Invitational, which started in 2003. Cheshire Academy hosts the race, during which numerous NEPSAC come to campus to compete, free of cost. Lunches and T-shirts are provided.

The cross country program prepares its student-athletes to be lifelong runners at the level they choose, whether that’s at the college level or running for fitness and pleasure.