A Bit of Everything
This steep route incorporates a variety of the very best features of Shenandoah National Park: rushing streams; waterfalls; wilderness cliffs; moss- and fern-carpeted forests; spectacular wildflowers, fall foliage, and ice formations, each in season, of course; rock outcrops; and expansive summit views. The route climbs through one of the park's most-scenic canyons, crosses Skyline Drive, and tops out on the summit of the park's highest peak, Hawksbill, where excellent 360-degree views await.
Mid-fall through early spring are the best times to go. You will avoid the summer humidity that way and will also have a better chance of enjoying haze-free views from Hawksbill. Winter may be the best time of all, as it is quiet, the air quality is usually pretty good, and ice often decorates the streamside rocks and cliffs (and sometimes the waterfalls freeze completely over).
At Sperryville along U.S. 211, look for signs indicating 522 and 231 and follow the directions to them. Turn right on 231. You can also reach 231 via 522 from Culpeper, and you can take 231 all the way from Charlottesville. After about 10 miles along 231, you reach a tiny town called Etlan. Look on the east side of the road for a small convenience store. Directly across the road from the store is SR 643. There should be a sign indicating access to Whiteoak Canyon. Follow this road for about 4 miles until you reach a stop sign. Turn right (a sign for Whiteoak Canyon should confirm this). You are now on SR 600, and it takes you all the way to the signed parking area and trailhead, almost at the very end of the road. Instead of turning into the parking area, continue straight for about 0.8 mi to the end of the road, which is where the Berry Hollow Fire Road begins. It is about 5 miles from the junction of 643 and 600 to the trailhead, and the drive takes about 15-20 minutes.
RT distance 8.4 miles; one-way elevation gain at least 2900' (ups and downs in the canyons will add from 100-300' more).
From the trailhead, hike for 0.2 mi along the Whiteoak Canyon Trail to its intersection with the Cedar Run Trail, which climbs 3.1 mi to Hawksbill Gap. At 0.8 mi from the trailhead, there is a stream crossing that is often tricky due to very slippery footing. The trail climbs steeply after this ford, passing three waterfalls, best viewed via short scrambles but still visible from the trail. The uppermost cascade is about 2.2 mi from the parking area.
At Hawksbill Gap, cross Skyline Drive and hike the Hawksbill Mountain Trail for 0.9 mi to Hawksbill's summit. There is a three-sided day-use shelter there in case you need to sit out a storm or need a break from the elements for any other reason.