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Day One: Ramsey's Draft
If you've ever wondered what Virginia looked like before John Smith, your answer lies in the Ramsey's Draft Wilderness (540-885-8028), about an hour's drive from Charlottesville, Virginia. Just north of U.S. 250, the little-traveled wilderness area holds some of the last stands of virgin hemlock and hardwoods in the East. Locals connect the ridge-top Shenandoah Mountain Trail, which serves up broad views, with the narrow Ramsey's Draft Trail, which threads through the best of the old-growth groves. The loop is 16 unblazed miles (26 kilometers), and you'll have to ford the namesake draft (that's Old Virginian for "stream") 15 or so times. Gladed meadows make for great midway campsites.
Day Two: Highland County, Virginia
Spend the morning hiking out of Ramsey's Draft, and then drive west through Highland County, known locally as Virginia's "little Switzerland." Say what? Skepticism is warranted, but Highland does claim the title for the highest county east of the Mississippi, and it's one of the least populated. The 200-person county seat of Monterey is about as much civilization as you'll find in Highland, and High's Restaurant, off Main Street, is a great place to grab a burger before taking to the back roads. North of town, County Route 642 turns into 15 miles (24 kilometers) of gravel west of Blue Grass (pop. 30) and heads into West Virginia through ramshackle farmland, forest, and black bear country.
Day Three: Seneca Rocks
From your tent at the Forest Service's Seneca Shadows campsite ($9), you'll be face-to-face with the 400-foot (122-meter) Tuscarora-quartzite fins that define climbing at Seneca Rocks, one of the East's centers for trad. A classic route is Soler, an exposed, two-pitch 5.7 that tops out on the highest part of Seneca's South Summit. The whole area makes a fantastic classroom. Join a class or hire a guide from Seneca Rocks Climbing School ($150; 800-548-0108; www.seneca-rocks.com).
Day Four: Elk River Touring Center
When mountain bikers dream, it's of places like Elk River. The center, located in Slaty Fork, West Virginia, has a comfortable lodge, an in-house bike shop, and more than 200 miles (322 kilometers) of trails out the back doornot to mention a gourmet restaurant ($68 and up for a room, $35 a day for a bike; www.ertc.com). The 13-mile (21-kilometer) Bear Pen Trail loop includes some of the most scenic and varied singletrack in the 900,000-acre (36,422-hectare) Monongahela National Forest. When your legs give out, fire up the motor and head south to scenic Route 150twenty-two miles (35 kilometers) of pullouts and car hikes along the Cranberry Wilderness (304-653-4826), the largest in the East. The road ends at the Cranberry Glades Botanical Area, a 750-acre (304-hectare) bog of deciduous forest, orchids, and bizarre insect-eating pitcher plants. Cap off the day high on the Blue Ridge Parkway for a smoldering sunset over Virginia's Shenandoah Valley.
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