The 7 Best Hikes in Virginia’s Blue Ridge Mountains and Shenandoah Region
Stretching from Shenandoah National Park to the southern reaches of the Blue Ridge Parkway, Virginia’s mountains are home to countless scenic trails — waterfalls, panoramic summits, and peaceful woodland paths. Whether you’re exploring the northern Shenandoah highlands or planning a stay near Wintergreen Resort, these seven hikes showcase the very best of the Blue Ridge.
Photo: Old Rag NPS / Public Domain
1. Old Rag Mountain — Shenandoah National Park
Distance: 9.2 miles loop | Difficulty: Strenuous
One of the most famous hikes in the eastern United States, Old Rag is a bucket-list climb through granite boulder fields and stunning summit views. The rock scramble near the top is part of the fun, and the 360° panorama is unmatched.
Pro tip: A day-use ticket is now required for access (check Shenandoah National Park’s official site before visiting).
2. Stony Man Trail — Shenandoah National Park
Distance: 1.6 miles loop | Difficulty: Easy to moderate
This short but spectacular loop delivers some of the best views in Shenandoah without the climb. The Stony Man Overlook gives you sweeping views of the Shenandoah Valley and Massanutten Mountain — perfect for families or casual hikers.
3. Humpback Rocks Trail — Blue Ridge Parkway (Milepost 6)
Distance: 1 mile each way | Difficulty: Moderate to strenuous
A classic Blue Ridge Parkway hike that packs a huge payoff. The steep but short ascent ends with panoramic views of Rockfish Valley and the Shenandoah ridgeline. Sunrise and sunset are both spectacular, and it’s just 30 minutes from Charlottesville.
4. Crabtree Falls — Blue Ridge Parkway (Milepost 27)
Distance: 3.4 miles round trip | Difficulty: Moderate
Virginia’s tallest waterfall, Crabtree Falls drops more than 1,200 feet over five major cascades. Wooden overlooks along the trail let you stop and admire the rushing water from different levels. It’s one of the most photographed hikes in the Blue Ridge Mountains.
5. Spy Rock — Near Montebello, VA
Distance: 3.1 miles round trip | Difficulty: Moderate
A short climb leads to an open granite dome with 360-degree mountain views — one of Virginia’s best panoramic summits. Located just south of the Parkway, Spy Rock offers a quieter experience than Humpback Rocks but equally impressive scenery.
Photo: Blackrock Summit Sunset - Shenandoah National Park Andrew Parlette from Elkridge,MD, US, CC BY 2.0, via Wikimedia Commons
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6. Blackrock Summit Trail — Wintergreen Resort (Blackrock Ridge Area)
Distance: 1.5 miles round trip | Difficulty: Easy to moderate
This hidden gem inside Wintergreen Resort winds through mountain forest to a natural rock outcrop with commanding Shenandoah Valley views. It’s a perfect late-afternoon hike before dinner — especially during fall foliage season.
7. Shamokin Springs Nature Preserve Trail — Wintergreen Resort
Distance: 1.2-mile loop | Difficulty: Easy
An easy, peaceful trail that showcases the natural beauty of Wintergreen’s ecosystem — ferns, small streams, and gentle woodland paths. Great for a quiet morning walk or a family-friendly nature outing right within the resort.
Where to Stay Near the Blue Ridge Parkway & Wintergreen Trails
With so many amazing hikes across Shenandoah National Park and the Blue Ridge Parkway, many travelers choose to divide their trip — spending a few days near the northern park and a few near Wintergreen for easier access to the southern trails.
For a luxurious, entertainment-focused stay in Wintergreen, consider Chateau Greenstone
Frequently Asked Questions
Q: Is the Old Rag Mountain hike open year-round?
A: Yes, Old Rag is part of Shenandoah National Park and typically accessible year-round, but from March 1 to November 30 you will need a day-use ticket to the Ridge/Saddle trail sections.
Q: Do I need a permit or reservation for the major hikes in this region?
A: In Shenandoah National Park many popular hikes (especially with rock scrambles) require a day-use permit, while trails on the Blue Ridge Parkway are generally open without special hiking permits (though parking lots may require fees).
Q: Where should I stay if I want to hit both the Blue Ridge Parkway hikes and the Wintergreen area trails?
A: Base yourself somewhere central so you can explore both regions. Staying at or near Chateau Greenstone in the Wintergreen area gives you excellent access to the Parkway heading south, plus those two hidden-gem Wintergreen hikes — making it a smart multi-day hub.
Q: Are the Wintergreen-area hikes suitable for beginners or families?
A: Yes — for example the Shamokin Springs Nature Preserve Trail is a gentle 1.2-mile loop inside Wintergreen, ideal for casual walkers and families.
Q: What time of year is best for hiking in the Blue Ridge/Shenandoah region?
A: Spring through fall offers the most comfortable trail conditions and stunning foliage. Winter hike conditions are possible but weather and daylight may restrict your options, so check forecasts and trail advisories ahead of time.
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