United States·2026

Winchester, VA-WV

Winchester sits at the northern gateway to the Shenandoah Valley with direct access to the Appalachian terrain that defines running and cycling here. Runners tackle the Seven Bends Aqua Blaze, a 11.27km duathlon that threads through local trail systems, while the longer Shenandoah River Adventure Race (96.6km) draws serious endurance athletes into the valley's mixed terrain. Cyclists dominate the region—the CCAP Benefit Bike Tour's 112.7km route and the Cacapon Enduro's 30.6km climbs exploit the ridgelines and river valleys within 20–40km, with sustained 5–8% grades through the Blue Ridge foothills at elevations between 300m and 900m.