Students also sit on the Judicial Board, which advises the Headmaster on major disciplinary cases. Because Winchendon believes that a carefully crafted athletic program can complement and enhance students' growth in other areas, participation in athletic activities is required for each season. Both boys and girls participate in intramural and recreational sports. Graduates of the basketball program are playing at numerous colleges and universities, including Notre Dame, Michigan, DePaul, Cincinnati, Florida State and George Washington University. A member of the class of '99 was drafted to play for the Dallas Mavericks organization.
Hockey is a traditionally strong sport at the school.
In 1998 they reached the semi-finals. Graduates of the Winchendon hockey program play at numerous schools including St. Lawrence, Merrimac, Niagra, UConn, and Curry. A member of the class of '99 was drafted by San Diego. Special-Interest Groups and Outings Students publish a yearbook, newspaper, and literary magazine.