Where to Hike Around Wintergreen Resort

shenandoah valley in virginiaSeeking an outdoor adventure in the clear mountain air surrounded by the area’s beautiful foliage? Discover the ample hiking opportunities at Wintergreen Resort!

Wintergreen’s trail system extends over 30 miles through rugged terrain and gently rolling hills, showcasing the beauty of the Blue Ridge Mountains and Shenandoah Valley any time of year.

Top 10 Wintergreen Resort Hiking Destinations

If you’re spending time at Wintergreen Resort, be sure to explore the beauty of the area and the diverse mountain terrain for yourself on Wintergreen’s best trails — where you can hike at your own pace and experience the spectacular views and wonders of nature.

Here are the best hiking destinations around Wintergreen Resort:

10. Trillium House Trail

Distance: 0.1 Miles | Difficulty: Easy

Stroll leisurely around the Trillium House garden in Wintergreen and still get a taste of the area’s immense beauty. In the warmer months, you’ll find beautiful wildflowers blooming all along the trail, which you can learn about through the nature center’s pathside signs.

9. Trillium Field

Distance: 0.1 Miles | Difficulty: Easy

Tour this trail in early May, when the white and pink trillium flowers cover every inch of the field and provide a truly spectacular experience. The Trillium Field is near the Wintergarden Pool & Spa, where Wintergreen Drive and Devils Knob Loop meet.

8. Ravens Roost Park

Distance: 0.1 Miles | Difficulty: Easy

A family favorite at Wintergreen Resort, the Ravens Roost Park trail loops around to a wooden overlook platform that showcases the stunning Shenandoah Valley extending beyond the treetops. In the fall, you can watch the vibrant leaves rustle in the winds and light the valley with oranges, reds, and yellows.

7. Shamokin Springs Nature Preserve Trail

Distance: 0.3 Miles | Difficulty: Easy

Take an outdoor tour of the nature center where you can truly experience the diverse terrain — like the wetlands layered with gurgling streams and stunning plant life — from within the Wintergreen Resort community. This mountain trail is another family favorite, offering great views of the area and choice opportunities for bird watching.

6. Upper Shamokin Falls Trail

Distance: 0.4 Miles | Difficulty: Moderate

The falls are a major appeal of this trail. Stay to admire the cascading waters and evergreens throughout the moderately short trail, and be sure to catch all views of the waterfall from different vantage points; the Upper Shamokin Falls Trail connects with Morgans Loop, which goes around the waterfall and stops along the top of the falls for a spectacular view.

5. Highlands Leisure Trail

Distance: 0.5 Miles | Difficulty: Moderate

Connecting Blackrock Village and Wintergarden at the resort, this leisure trail takes hikers on a journey through Wintergreen’s ancient forests and rocky mountain terrain. On the highest point of the trail, hikers can view the ski slopes and sweeping views from the overlook. It’s a great choice for outdoor exploration that doesn’t take a long time to access.

4. Devils Knob Trail

Distance: 0.6 Miles | Difficulty: Moderate

Discover the beautiful white flowers emerging from within rock crevices in the bluffs, especially in the spring, and capture stunning views along your trek through the trail’s rocky terrain. The trail starts on Devils Knob Loop in Wintergreen Resort.

3. Chestnut Springs Trail

Distance: 1.1 Miles | Difficulty: Moderate

Cross babbling streams and wander through the towering birch trees on this trail, and make sure to visit during April, when the spring wildflowers bloom into a vibrant quilt on the forest floor. In the fall, you’ll find that the trees turn shades of fiery red and golden yellow.

2. Upper Shamokin Gorge Trail

Distance: 0.8 Miles | Difficulty: Difficult

The Gorge Trail is one of Wintergreen Resort’s most difficult trails, but it’s worth the challenge for hikers. The trail crosses Stoney Creek in several spots, and the bubbling waters are often within earshot of the trail, providing a natural musical background on your hike.

1. Old Appalachian Trail

Distance: 3.3 Miles | Difficulty: Difficult

A favorite among local hikers, the Old Appalachian Trail — which was once, as its name suggests, part of the Appalachian Trail — showcases the centuries-old heritage of the mountains with its ledges and rocky terrain. It’s a true treat for hikers who explore all of the trail diversions and view the Shenandoah Valley from their perch on scenic vistas along the paths.

Live Where the Outdoor Activities are Abundant

The best way to enjoy your surroundings is in a residential community that enjoys outdoor adventures and the best lifestyle. If you’re eager to find your niche in the Wintergreen Resort area and have access to the area’s best hiking trails, contact us, your Wintergreen Resort real estate experts!

We can help you find the condo or mountain home of your dreams and provide you with local information and real estate resources. Interested in exploring a home for sale at Wintergreen Resort? Call us at (877) 296-9860 or service@gowintergreen.com today!

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