Chimney Rock

Starting from the Riprap Parking Area at mile 90 on Skyline Drive, you'll immediately drop into the Shenandoah Wilderness on a well-worn path that trades the busy overlooks above for genuine backcountry quiet. The trail descends through a hardwood canopy — oaks and hickories that turn electric in October — before the forest opens up and the rocks start demanding your attention. The final approach to Chimney Rock involves picking your way across tilted slabs and fractured columns of greenstone, remnants of ancient lava flows that look like a giant's discarded building blocks. The payoff is a wide-open perch with views stretching across the Shenandoah Valley that rival anything on the more popular trails up north. At roughly three and a half miles round trip with a moderate climb back out, this one hits the sweet spot for hikers who want a real destination without an all-day commitment.