Part of the North Adams Public School District, it serves students in grades 7–12 from North Adams and the towns of Clarksburg, Florida, and Monroe.

Drury competes primarily within Berkshire County, though a small portion of its non-league independent schedule includes similar-size schools from the Connecticut River Valley of Western Massachusetts and nearby Vermont.

Their traditional rival is Hoosac Valley High School in Cheshire.

[citation needed] However, in the present day, many consider the rival to be McCann Technical High School.

Nathan Drury High School was founded in 1843 by a grant of $3,000 left in the will of Nathan Drury, a wealthy farmer of the Town of Florida, Berkshire, Massachusetts.