Regardless of what criteria you use to create your own “bucket list” of hikes, there are trails in the Shenandoah Valley that will meet your requirements. Virginia’s state parks, national parks and national forests comprise thousands of miles of dirt paths–as easy or as challenging as you want.
For example, about 554 miles of the Appalachian Trail cross Virginia—more than any other state. About 101 miles of it go through Shenandoah National Park. In George Washington and Jefferson National forests, you’ll find a combined 1.8 million acres in total– one of the largest expanses of public land in the eastern United States. They include 325 miles of the Appalachian Trail, 23 Wilderness areas, and 2,340 miles of perineal streams.
Virginia’s 37 state parks include several in the Valley—Shenandoah River State Park, Natural Bridge, and Douthat among them.
To help you narrow down where to go, and accepting that everyone has a different idea of what makes their “bucket list,” we suggest the following trails as warranting serious consideration.
Starting from the north end of the Valley:
Devil’s Nose Trail
A favorite with locals in West Virginia is the Devil’s Nose trail, which has a spectacular overlook and passes through natural habitats of mountain laurel, rhododendron and hemlock groves. (Devil Nose is in Sleepy Creek Wildlife Management Area, a popular hunting spot, so wear blaze orange during any hunting season.) This hike takes you down rugged trails to a stream with numerous rapids, rock formations, a waterfall, and ten-foot high blooming rhododendrons in spring. Plan on 1 to 1 ½ hours round trip. Devil’s Nose parking area is about 30 minutes from Martinsburg. Take Rt. 9 West through Hedgesville, turn left on Mountain Lake Road, then turn right onto Audubon Road through the Sleepy Hollow subdivision. Turn right onto Maverick road, and follow it until you see the parking area. Find out more at the Martinsburg/Berkeley County WV Convention and Visitors Bureau.
The Appalachian Trail in Virginia
The AT’s northern entrance to Virginia is at the state line in Clarke County (and the Appalachian Trail Conservancy is just up the road in Harpers Ferry.) Virginia has 15 “Appalachian Trail Communities,” a designation towns must apply for and earn. Essentially, it means they welcome AT hikers and make a special effort to provide services for them. In the Shenandoah Valley, AT Communities, include: Berryville, Front Royal, Luray, Harrisonburg, and Waynesboro.
Lengthy sections of the AT parallel or cross Skyline Drive and, further south, the Blue Ridge Parkway. The Appalachian Trail Conservancy considers the Shenandoah National Park section to be excellent for beginning hikers. The trail is very well maintained (by the Potomac Appalachian Trail Club) and climbs are usually less than 1,000 feet. The AT is marked with white blazes; it exits Virginia just east of Bristol.
Old Rag Mountain
Widely considered the most challenging hike in Shenandoah National Park, Old Rag is a 9.2 mile circuit rated “very strenuous” by Park officials. Parts 
of the trail involve a true rock scramble that is not for the weak of heart. But views are spectacular at any time of year, especially from the 3,291-foot summit. If you could only do one hike in the Valley, Old Rag would be a good candidate. Stone pillars help you find your way on many of the park’s trails, but mapping out your route ahead of time is advised. (Deep in forested canyons, GPS may not always work.)
From the intersection of US 211 and US 522 in Sperryville, take US 522 south for .8 mile to VA 231. Turn right on VA 231 and follow it 8 miles to VA 601, Peola Mills Road. Turn right on VA 601 and follow it .3 mile cross the Hughes River, then veer right, staying with VA 601. Stay with the blacktop as it becomes Nethers Road and leads up the Hughes River valley to the lower Old Rag parking lot at 3.3 miles. Parking is available for about 265 cars, but you’d be surprised how fast it fills up on weekends.
Upper Hawksbill Mountain
A “moderate” two-mile up and back hike that takes you to the highest peak in Shenandoah National Park, at 4,049 feet. Nearly 360-degree views of the Valley from an observation platform are incomparable. Start at the Upper Hawksbill trailhead, on the west side of Skyline Drive at milepost 46.7, or consult park maps for other routes. Lucky hikers may get a glimpse of the once-endangered peregrine falcon, whose numbers are increasing due to restoration projects in various parts of Virginia, including Hawksbill Mountain.
Dark Hollow Falls
Without doubt one of the best family hikes in the Valley, down to one of the most popular waterfall hikes in Shenandoah National Park. Its singular 
beauty and relative ease of access make it appealing for parents with young children. The trailhead and parking lot are right on Skyline Drive between mileposts 50 and 51. It’s all downhill till you get to the bottom of the 70-foot falls, and it’s quite steep on the way back, but the whole hike is just 1.4 miles round trip. After the hike stop in at the Byrd Visitor Center, about a quarter mile south of the trailhead, on Skyline Drive.
Humpback Rocks
Starting from nearby Waynesboro, take the Blue Ridge Parkway to the Humpback Rocks Visitor Center (540) 943-4716) at MP 5.8. You will find both beauty and history here. The rocks served as landmark for wagon drivers hauling goods along the old Howardsville Turnpike, an important route across the Blue Ridge until the railroads got there. A museum next to the Visitor Center illustrates the life of the 19th Century farmers. There are actually several trails, and getting to the rocks requires a short, but significantly steep climb. A one-way hike to the Humpback Rocks picnic area is 3.9 miles, starting from the parking area at MP 6 on the BRP, and there are shorter routes to consider. If you want a 360-degree view, this is a good one—the Blue Ridge, the Alleghenies, the Shenandoah Valley and the Piedmont to the east are all clearly visible. “
Peaks of Otter
Three mountaintops near Bedford are collectively known as Peaks of Otter—Flat Top is 4.4 miles one way to the 4,004-foot summit. Sharp Top (1.5 miles to the 3,862-foot summit) is probably the most popular of the three, but is steep and not easy. Harkening Hill is 3.3 miles to the top, at 3,375 feet, and goes by an enormous boulder balanced on a small rock. All offer splendid views. Get more information at the Peaks of Otter Visitor Center, MP 85.9 on the Blue Ridge Parkway. Make Peaks of Otter Lodge your home base for hiking these trails.
Banner photo of Hawksbill Summit by NPS/Katy Cain