It was established in the fall of 1972, when the county combined Charles Town, Harpers Ferry, and Shepherdstown High Schools.

The Cougars have won 12 state championships, most recently winning back-to-back titles in 2015–16.

The Cougars' boys track team has won six state championships, including four straight from 2010–2013.

Notable graduates include former NFL wide receiver James Jett and former NFL safety Dewey McDonald and MLB first-round draft pick Josh Cenate.

A notable achievement includes the honor of marching in the Cherry Blossom Festival in Washington D.C. in April 2013, 2015, and 2022.