The school is located on grounds donated by the Lapham family, carving off approximately 46 acres of Waveny Park.

[12] In August 2018, two lunch ladies[clarification needed] from the school were arrested and accused of stealing about $500,000 from the cafeteria over a five-year period.

[14] School teams have won state championships in football, lacrosse, soccer, basketball, swimming, golf, tennis, track and field, and cross country.

[15] The school's football team, dubbed the Rams, has been led to 12 State Championships by coach Lou Marinelli, whose overall record at New Canaan is 321 wins, 96 losses, and 6 draws.

[17][18] Also in 2019, the team won the Connecticut Interscholastic Athletic Conference (CIAC) Division IV championship for the first time since 1962, defeating Granby Memorial High School 55–39.