Weaving around car-size boulders to the summit of 3,268-foot Old Rag Mountain is the quintessential Shenandoah thrill–and its airy precipice is also the best place for 360-degree views (especially for leafpeeping in early November). But unknown it is not, so pack a headlamp and set out on this 8.6-mile circuit three hours before sunset to enjoy a crowd-free summit. Take the Ridge Trail up shady switchbacks to an open ridgeline and two miles of scrambling to the Big Whoa–a sweeping panorama of mountainsides. Descend via the Saddle Trail and Weakley Hollow Fire Road to close the loop.
More Info: Shenandoah National Park, (540) 999-3500; nps.gov/shen
-Mapped by Ivan Levin