Shenandoah National Park
28 miles
2-3 days

Here’s a loop recommended by Backpacker magazine a few years back that includes the grail of Shenandoah hiking and much more. Start with a little history by hiking from Skyline Drive down to Corbin Cabin, which dates to 1909 and provides a glimpse into the Shenandoah’s pre-park past. Continue down the Nicholson Hollow Trail and pick up the Ridge Trail to climb over Old Rag, at 3,291 feet, and its associated ledges, which require some scrambling (it’s especially important to have a balanced pack on this hike). Relief comes in the form of a descent down the Old Rag Fire Road.

Another loop takes you down the Whiteoak Canyon and Cedar Run Trails, steep gorges with a combined nine waterfalls (water isn’t an issue on this circuit), before hooking up with the Appalachian Trail and a return to the trailhead. Camping is prohibited above 2,800 feet on Old Rag, and a backcountry camping permit is required, but is free. Dogs are not allowed on the Ridge Trail.

Especially for backpacking, Old Rag should not be attempted in bad weather, or even weather that looks like it might be thinking about going bad.

More info: http://www.nps.gov/shen/planyourvisit/upload/old_rag_combined_2013.pdf

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Type of hike: circuit
Trailhead: Corbin Cabin Cut-Off Trail parking, Milepost 38, Skyline Drive
Distance from downtown Charlottesville: 65 miles (1 hour, 30 minutes)
GPS: 38.36894, -78.21016
Camping: Forbidden above 2,800 feet on Old Rag,
Reservations? Backcountry permit required, by going here. http://www.nps.gov/shen/planyourvisit/campbc_permit.htm
Map here.
Cost? No.
Seasonal? Skyline Drive is often closed in winter; best in fall, after the summer crowds to Old Rag have dwindled.

Photo: HikingUpward.com