A Guide to Wintergreen’s Gorgeous Hiking Trails

Updated on: May 23, 2025

Skiers love hitting the ski slopes in Wintergreen, Virginia every winter, but what can you do in the spring and summertime? Are you an avid hiker who enjoys the journey just as much as the destination? The Wintergreen region has a trail system that spans for miles upon miles and appeals to hikers of every skill level. You’ll see waterfalls and wildflowers, vast mountain vistas, rock formations, natural springs, and more as you go hiking or mountain biking.

Are you trying to explore the Blue Ridge Mountains region but don’t know where to start or where to stay? Do you want a more homey and spacious place to stay while you explore Wintergreen Resort? Check out our Wintergreen Resort trail guide, then book one of our two rentals to see which one fits your needs best after a long day of adventure.

How many hiking trails does Wintergreen Resort have?

Wintergreen has over 30 miles of trails to explore, and you can spend days taking in the sights, getting back to nature, and enjoying unspoiled vistas. Several trails can be found very close to the ski resort itself. The Nature Foundation at Wintergreen offers trail maps and information to get you started with the local trail system.

Trails here are appropriate for every age group and experience level. You can find easy trails, wildflower trails, valley trails, vista trails, trails highlighted by cascading waterfalls, and trails featuring stunning rock formations. You and your elementary schoolers, teens, and even preschoolers can explore these beautiful trails, some of which are famous among hikers.

Looking for a longer trail in the Wintergreen ski resort area?

The longest trail in the Wintergreen area is also one of the most difficult to traverse. This is the Three Ridges Trail. It’s 13.3 miles long and is estimated to take just under eight hours to traverse. It is not recommended for inexperienced hikers, and if you do not have experience, it may take longer to explore its entirety.

One thing is certain: After this trail, you will need some time to rest and recharge. Check out one of our newly renovated rental properties for all the rest and relaxation you need after a day of adventure and sightseeing.

Ranking of hiking trails at Wintergreen Resort from easiest to hardest

Wintergreen offers trails for hikers of every level. The first thing to understand is the “blaze” color scheme for trails that denotes accessibility and where they generally take you. Yellow blaze trails are access trails, while red blaze trails are perimeter trails. Blue trails are valley trails.

Easy hikes

Easy hikes usually feature flat terrain with little to no elevation. Some may be paved or have paved areas. Some of the easier hikes in the area include:

• Shamokin Springs Nature Preserve Trail: Only 0.3 mile loop trail. Easy and fun for the family. Lots of wood bridges and stream crossings. Great for kids and dogs. Located at the intersection of Shamokin Springs Trail and Blue Ridge Dr.
• Stoney Creek Park: This one-mile, one-way trail features a paved walkway along the shores of a babbling brook, and it includes a valley picnic spot. It is not a loop trail.
• Loggers Alley Trail & Access: This red-yellow blaze trail is easy to moderate difficulty and offers leisurely walking and bird-watching. It’s located on an old logging road and ends at the Shamokin Gorge, connecting to the Upper Shamokin Gorge Trail.

Moderate trails

Moderate trails tend to have a higher elevation gain and short to medium stretches of strenuous uphill hiking. Some of the more popular moderate trails in Wintergreen include:

• Shamokin Falls Trail: This trail features two levels: the Lower Shamokin Falls and the Upper Shamokin Falls Trail. The Lower Shamokin Falls trail is 1.7 miles and blue blaze. The Upper Shamokin Falls Trail is just under a half mile and yellow blaze. Though moderate in difficulty, it is a family favorite.
• White Oak Trail: The White Oak Trail is a moderately difficult half-mile trail featuring wildflowers and morning bird-watching. It’s a yellow blaze trail.
• Devils Knob Trail: Devils Knob is one of the more famous trails in the region.
• Cedar Cliffs Main Trail: This trail winds through the forest and finishes on a cliff overlooking the Shamokin Gorge. It is parallel to the Cedar Cliffs North Trail.
• Chestnut Springs Trail: The Chestnut Springs Trail covers 1.1 miles and is a yellow-red blaze trail with north-to-south exposure.
• Pauls Creek Trail: This 0.6-mile trail is a blue blaze trail featuring a waterfall and a swimming hole.

Difficult trails

Difficult and rugged trails are for experienced hikers only. If you are not experienced, we do not recommend tackling these without a skilled hiker to guide you. In addition, inexperienced hikers can expect these to take much longer to complete.

• Blackrock Trail: The Blackrock Trail is just under a mile and is a red blaze trail offering rock climbing opportunities and tons of plant life.
• Brimstone Trail: The Brimstone Trail is just under a mile and is exceptionally difficult. It is a rocky red blaze trail that offers spectacular views.
• Crabtree Falls Trail: This trail is about 34 to 45 minutes away from the resort and offers three waterfalls during the hike. It is a somewhat challenging all-day trip with steps built into the trail. Multiple small, clean pools can be found along the way, and you can get into the water and dip your head behind some of the falls.
• Fortunes Ridge Trail: This trail is rated moderate to difficult and covers 1.1 miles. It’s a red blaze trail featuring dense forest, waterfalls, and wild rhododendrons growing on cliffsides in the spring.
• Hemlock Springs Loop: Rated moderate to difficult, this yellow-red blaze trail offers north vs. south slopes along a natural stream and deep groves of old-growth hemlock along the way. It’s just under a mile long.
• Old Appalachian Trail: This trail is immediately off Laurel Springs Drive and Fawn Springs Drive. It’s a short, flat walk from the road to the trailhead, which is clearly marked. Not long after embarking on your hike, you will discover absolutely magnificent vistas.
• Three Ridges Trail: This ultra-challenging hike traverses more than 18 miles. It is a bit long to cover the entire thing in a single day, but you can reach the first summit and head back. The trailhead offers a parking lot just off the Blue Ridge Parkway, and it is just a short drive from the ski resort.
• Pedlars Edge Trail: This red blaze trail features bird-watching and incredible geological formations along the way. It covers just 1.6 miles but is rated as a difficult trail to traverse and is recommended for experienced hikers.

What to bring for a hike at the Wintergreen ski resort

When you go hiking, be sure to plan accordingly and use all the safety measures you can. Hike at your own risk, and never do it alone. Do not underestimate the dangers of the natural terrain, and be sure to carry high-energy snacks and enough water to stay hydrated. Respect wildlife and keep your distance. Wear solid hiking footwear and proper attire, and always carry a trail map with you. Know your limitations, and do not try to push yourself on unfamiliar trails. Finally, stay on clearly marked paths.

After a long day, come back to the rental and enjoy your night

After a long day, you can come back to your Devils Knob rental and enjoy your night. Our two-bedroom and three-bedroom spacious newly renovated rentals offer plenty of room for you, your buddies, and all your camping gear. We have space for it all.

Ready to expand your horizons?

With vista and valley trails, waterfalls, forested canopies, and more, hiking in Wintergreen is a breathtaking experience that offers worlds of memories. If you have questions or would like more information about our luxurious rental properties, you can contact us through the individual property pages on AirBnB or Vrbo.