Shenandoah – Virginia


Rockfish Gap Entrance | Dark Hollow Falls | Old Rag Mountain

Date of Visit: April 14-15, 2014 & October 13-15, 2019

How we got there: 2014: Drove from Charlottesville, VA, a half hour from the Rockfish Gap Entrance.
2019: Drove from Baltimore and entered at Thornton Gap.

Lodging: 2014:Skyland Resort, 2019: Airbnb on a farm near Madison, VA.


  • Skyline Drive – Runs 105 miles through the entire length of the park and has 75 scenic overlooks.
  • Dark Hollow Falls – The most popular trail in the park leads 1.4 easy-moderate miles down to a multi-tiered waterfall.
  • Stony Man Trail – Easy 1.6-mile trail with 340 ft elevation gain leads to the rocky summit of Stony Man Mountain, which looks like the profile of a man from below. Part of the route follows the Appalachian Trail. Trailhead is adjacent to the Skyland Resort.
  • Hawksbill Mountain – Upper Hawksbill Trail is a 1.7-mile route with 690 ft elevation gain. Leads to an observation platform at the highest point in the park, at 4,050 ft.
  • Old Rag Mountain – 9.5 mile round trip hike with 2400 feet of elevation gain. Hiking the loop clockwise, there are a couple miles of rock scrambling on the way to the summit. It was more rugged than expected, but it’s really fun if you don’t mind a little slow going.

Tips: This park is very long and skinny, plan plenty of time to leisurely drive the entirety of Skyline Drive with its 35mph speed limit.

Next time: Hike in the more remote northern and southern extremes of the park, like Overall Run Falls or the Riprap-Wildcat Ridge loop.