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Whiteoak Canyon -> Nicholson Hollow -> Old Rag Circuit

A challenging, but epic, overnight loop showcasing Whiteoak Canyon and Old Rag Mountain.

Hiking Severe

28 km
1.5 km
1.5 km
1 day +
Low Point
278 m
High Point
1 km
Whiteoak Canyon -> Nicholson Hollow -> Old Rag Circuit Map

This overnight circuit pairs the stunning waterfalls and cascades in White Oak Canyon with a visit to Old Rag - one of the most coveted hikes in the park. It's a spin on a loop recommended by Shenandoah National Park on this backpacking guide. Instead of following an old fire road, our version treks up and over Old Rag Mountain on day two. The park considers this one of the most popular, yet dangerous, hikes around and even proclaims Old Rag as "one of Shenandoah's premier experiences!"


This route does not begin on Skyline Drive, but along Route 600 near Syria. It's in the central district, along the easternmost edge of the park. Other maps list it as the Whiteoak Canyon Parking Area.

For day one, plan an early start and follow Whiteoak Canyon up from the trailhead. While it is a stunning area of the park, it "receives extraordinarily high use on weekends," the NPS warns. Whether you're day hiking or heading out for an overnight, you should start as early as possible to avoid the crowds. This circuit would be best on a weekday, not a weekend.

After leaving Whiteoak Canyon, you will spur right onto a horse trail, hike a couple of miles on an old fire road, then turn onto Indian Run Trail. From here, the trail descends to Nicholson Hollow Trail. Turn right (eastbound) and look for a campsite after walking half a mile. The NPS highlights abundant camping for the next mile or two, so you shouldn't have an issue finding a quiet site.

For day two, you'll continue down Nicholson Hollow Trail, then turn right on Route 600. There are several notable river crossings along the way, so prepare for knee to waist high water in the spring or after heavy rains. One key highlight of the trail, however, is its "excellent swimming holes that exist even in drought," according to the NPS.

After a brief road walk on Route 600, you'll reach the trailhead for the traditional Old Rag Loop. The NPS suggests taking Weakly Hollow Fire Road back, but the trek over Old Rag is extremely rewarding - should you have some energy saved for the challenging scramble to the summit.

Dogs are allowed if you bypass Old Rag Mountain, but they are not allowed anywhere near the summit.

Sources: https://www.nps.gov/thingstodo/hikewhiteoakcanyon.htm https://www.nps.gov/shen/planyourvisit/upload/SHENBCTrip-WhiteoakCanyonandNicholsonHollowE060-508.pdf



Hiking challenging trails where simple scrambling, with the occasional use of the hands, is a distinct possibility. The trails are often filled with all manner of obstacles both small and large, and the hills are very steep. Obstacles and challenges are often unexpected and can be unpredictable.

High Exposure

3 out of 4

Some trail sections have exposed ledges or steep ascents/descents where falling could cause serious injury.


3 out of 4

Little chance of being seen or helped in case of an accident.

Best time to visit

all year round


  • Wildlife
  • Historical
  • Picturesque
  • Summit Hike
  • Wild flowers
  • Water features
  • Forestry or heavy vegetation

Similar routes nearby

Guidebooks in this area