Warren County competes in VHSL activities in the Evergreen District, Region II, Group AA.
County population growth, particularly accompanying the American Viscose rayon factory opening, necessitated a new high school building, occupied in 1940.
The impressively sited, Classical Revival-style, Works Progress Administration-funded building was erected on Luray Avenue, and originally housed grades eight through twelve, but is now Skyline Middle School.
Because WCHS was the only high school in the County (no "separate but equal" black high school), and local authorities were not ready to comply with U.S. Supreme court-ordered integration, WCHS was ordered closed by the Governor in the fall of 1958, as part of Virginia's "massive resistance" to implementation of the U.S. Supreme Court's decision in Brown vs. Board of Education.
Although the high school building was closed, education continued in donated private and church spaces.
Many seniors transferred to neighboring Rappahannock County (where an even smaller black population was not as politically active and the integration issue was not forced).
Also in the fall of 1959 (after a hurried construction process) John S. Mosby Academy (grades 1-12), one of Virginia's several segregation academies opened, as well as public Criser High School, serving the black high school student population of Warren and Rappahannock counties (Criser was an effort to provide "separate but equal", segregated facilities).
Black students continued to have a choice in high schools until Criser closed in 1966 due to declining enrollment.
Overcrowding was alleviated again in the late 1970s, with the construction of the Fine Arts wing (which included a new gymnasium and new library in the old gym) and the Vocational Technology (also known as the "Vo-Tech") building.
Warren County's basketball teams began to achieve some success in the late 1970s under long-time head coach Jim Moose.
Lee-Staunton were dominant during this era, Moose's Warren County teams provided Lee and other Region II powers with good competition.
The overcrowded high school became a political issue during the late 1980s as Warren County's population grew.
A revival of the football program also occurred starting in 2003, with new coach Heath Gilbert leading the Wildcats to three straight 6-4 seasons with the single wing offense, and running back H.B.
Students at WCHS (and Skyline) are also eligible to apply to Mountain Vista Governor's School to take advanced math, science, humanities, and research courses.
Led by Tony Tallent, the football team won a district title in 2012, followed by several successful seasons with winning records.
Wrestling has become a dominant program under coach Matthew Wadas and recently had a two-time state champion in Zach Beckner (2015, 2016).