The Winchendon School is a coeducational, preparatory boarding and day school composed of two campuses; one in Massachusetts, and another in Herald Square, Manhattan, New York.

The school community includes students in 9th grade to students in 12th grade, as well as post-graduates (PGs).

The Winchendon School offers a total of $3 million in needs-based grants to its students every year.

[2] The Winchendon School offers courses in world languages, computer science, engineering, English, history and social science, mathematics, performing arts, visual arts,[3] and is recognized for its academic support center, named after the school's founder, Lloyd Harvey Hatch, Sr.[4] The Winchendon School's athletic teams are known as the Wapitis, and their colors are dark gray, kelly green, and lime green.

The following competitive sports are offered at The Winchendon School:[5] Winchendon is a part of New England Preparatory School Athletic Council (NEPSAC).