Best Hikes Near Winchester

Winchester Sits Within Reach of Two State High Points

Winchester's own Shenandoah Valley terrain is mostly local parkland and Appalachian Trail access points, but head west and the country changes fast. This guide's closest tracked trail, Dans Rock in western Maryland's Allegheny Highlands, is about 50 miles and a 66-minute drive. Push a little farther and Winchester turns out to be one of the few cities within day-trip range of two separate state high points: Pennsylvania's own Mount Davis and Maryland's own Hoye-Crest, both under 95 minutes out. Farther still, West Virginia's Canaan Valley and Dolly Sods high country — several summits topping 4,000 feet — sit inside the same two-hour window.

This guide covers all 40 trails within 100 miles of Winchester, sorted by actual distance from real trailhead coordinates — not the city center. Each trail includes:

• ✓ Exact distance from Winchester (measured from the trailhead, not the summit)
• ✓ Trail difficulty rating (easy, moderate, hard)
• ✓ Elevation gain & distance
• ✓ Parking information & fees
• ✓ Interactive trail maps
• ✓ Real-time weather conditions