A member of the Berkshire County League under the
MIAA, Lenox sports teams are known as the
Millionaires in recognition of the town's prominence as a summer colony for some of the country's wealthiest families during the
Gilded Age of the late 1800s. However, many students have expressed dismay with the "Millionaires" moniker, arguing that it promotes an elitist and revisionist version of the town's history. Numerous efforts to change the sports teams' name have been unsuccessful. The school's colors are maroon and gold. The chief rival are the
Wildcats of
Lee High School, in the nearby town of Lee. A rivalry has developed over the years with the
Mounties of Mt. Greylock High School in
Williamstown for both boys and girls cross country running and skiing. Fall sports include soccer, cross country running, volleyball, football, crew, and golf. Winter sports include alpine & nordic skiing, basketball, hockey, and swimming. In the spring the sports offered are tennis, baseball, softball, crew, track & field, and lacrosse. A wider variety of sports are made possible through partnerships with other high schools. These co-ops include hockey with
Taconic High School, swimming with Monument Mountain Regional High School in Great Barrington, and football with Lee High School. The Millionaires have a history of success in athletics across the board, particularly in cross country running, soccer, and skiing. The boys nordic program has won 8 Massachusetts state titles while the girls have won 15 - most recently in 2020. ==Rejection of regionalization==