The Pioneer District comprises high schools in the Alleghany Highlands and the Roanoke, New River, and southern Shenandoah Valleys.
This Alleghany Highlands is probably best known for being the home of or at least nearby five-star vacation resorts such as The Homestead and The Greenbrier, the latter which is in West Virginia.
One notable exception to this is football, with Highland High School not participating because of its small enrollment.
Due to its size, Parry McCluer has dominated most of the district's sports in recent years, culminating with their winning of 5 state football championships.
The new, larger Alleghany High School has since adopted Covington's Cougar nickname