Goal-setting and challenge, teamwork and self-confidence, succeeding and failing, are some of the lessons learned and values strengthened through involvement in interscholastic sports.
CSW offers students multiple sports team opportunities through all seasons of the year. The school competes in several league championships, often capturing titles and invitations to participate in higher tournaments. CSW's girls' varsity soccer team have won the Independent Girl's Conference League Championship, and both the girls' and boys' varsity soccer teams have been selected to participate in the new England Preparatory School Athletic Council (NEPSAC) soccer tournament. In addition, CSW's Ultimate Frisbee "A" team has ranked in the top 10 in New England.