We offer 18 interscholastic programs at the Varsity level, with many of those having sub-varsity level teams. In addition, we have 10 non-competitive, non-interscholastic programs offered throughout the year.

All students are required to participate in an Afternoon Activity for all 3 terms – Fall, Winter, and Spring.

Afternoon Activity Guidelines

For underclassmen (9th / 10th): Competitive Afternoon Activity offerings must comprise two out of three seasons.

For upperclassmen (11th / 12th / PG): Competitive Afternoon Activity offerings must comprise one out of three seasons.

*Full IB students are allotted one independent season per school year.

Please note the following:

Managing a sport DOES complete a competitive requirement.

You can request to participate in an Independent Activity, however, Independent Activities MUST be in line with the Annual Competitive Activities Requirements Guidelines. An Independent Activity must also be approved by a Parent/Guardian and Associate Head of School David Dykeman. An Independent Activity DOES NOT count as a competitive athletic offering even if you are participating in an independent sport.

Cheshire Academy is a member of the New England Prep School Athletic Conference and compete against some of the top regional prep schools within our greater region, as well as throughout the Western portion of New England.

Cheshire Academy features a multi-purpose turf field, a six-lane track, three multipurpose grass playing fields, baseball and softball fields, a two-court basketball & volleyball gymnasium, a 50M six-lane pool, six tennis courts, a fitness center and a comprehensive weight room and athletic training facility.

Questions related to Athletics and the Afternoon Program can be directed to athletic director Jim McCarthy at James.mccarthy@cheshireacademy.org.

We are staffed full-time with two Certified Athletic Trainers who cover our home games and work with athletes on their rehabilitation programs, as well as offer general strength and conditioning support to athletes.

We encourage students to try something new and give it a shot. Many sports have tryouts for the varsity team, but our numbers generally allow a spot for all who are interested at the sub-varsity levels. Competitive team sports are an important part of the Cheshire Academy experience and teach life skills like teamwork, good sportsmanship, and commitment. 

We have entered into an All School Agreement with Under Armour to outfit all of our Varsity teams in Under Armour uniforms. As of the 2015-2016 school year, all Varsity programs wear Under Armour. We also offer plenty of Under Armour products in our School Store.