8
runners
3
runs
Jogging around Wintergreen offers diverse terrain within Virginia's Blue Ridge Mountains, characterized by extensive woodlands and varied elevation. The region features an extensive trail network, with paths winding through lush forests and offering views of the surrounding valleys. Joggers can experience routes ranging from gentle paths to more challenging trails with significant elevation changes. The higher elevation provides cooler temperatures, making it suitable for outdoor activity.
Last updated: May 21, 2026
5
runners
5.85km
00:41
190m
190m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
runners
13.2km
01:47
380m
380m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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1
runners
9.89km
01:12
130m
130m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The Slacks Overlook Trail peers over the 20-minute Cliff area on the Blue Ridge Parkway. There are great views of the Copelands Rocks to the south and Upper Sherando Lake to the north.
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Wintergreen offers a diverse network of trails suitable for running. Our guide features 5 curated routes, ranging from moderate to difficult, allowing you to explore the Blue Ridge Mountains. Many of these trails are part of Wintergreen's extensive 30-mile trail system.
The terrain around Wintergreen is quite varied, reflecting its Blue Ridge Mountain setting. You'll find everything from mostly flat paths, like those around Lake Monocan, to uneven terrain with small hills, and even steep sections with rocks and roots for more challenging runs. Routes such as The Priest loop from Three Ridges Wilderness feature significant elevation gain, while Turkey Pen Forest Road loop offers a more moderate experience.
Yes, Wintergreen's trails are known for their beautiful natural features. You can find routes that lead to stunning waterfalls like Shamokin Falls and White Rock Falls. Many trails also offer breathtaking panoramic views of the Blue Ridge Mountains and the Rockfish and Shenandoah valleys from overlooks such as Ravens Roost Overlook and Three Ridges Mountain Overlook.
Wintergreen is excellent for running throughout much of the year. Its higher elevation (around 3,500 feet) provides cooler temperatures, making it a comfortable escape, especially during warmer months. Autumn is particularly stunning due to the vibrant fall foliage, offering picturesque views during your run.
While many routes in our guide are moderate to difficult, Wintergreen does offer options for less strenuous runs. The 2-mile path around Lake Monocan is a great choice for a flat, scenic jog. For a moderate trail with forest views, consider the Devil's Knob Overlook loop from Wintergreen.
Yes, many of the running routes in Wintergreen are designed as loops, offering a convenient way to start and end your run at the same point. Examples include Devil's Knob Overlook loop from Wintergreen and Sherando Loop overlook loop from Sherando Dam, both providing varied scenery.
Beyond the natural beauty, you might encounter interesting points along the trails. The Humpback Rocks Trail is a popular area with historical significance, and the nearby Humpback Rocks Visitor Center offers insights into the region. The Nature Foundation at Wintergreen also provides educational opportunities about local flora and fauna.
Wintergreen offers a range of difficulty levels. Our guide includes 2 moderate routes and 3 difficult routes, catering to different fitness levels. You'll find trails with gentle inclines and others with significant elevation changes, such as Slacks Overlook Trail loop, which is rated as difficult.
For families looking for a less strenuous activity, the path around Lake Monocan is a great option. While our featured running routes tend to be more challenging, Wintergreen's extensive trail network includes many paths suitable for a leisurely jog or walk with children, especially those with gentler grades.
The komoot community frequently praises Wintergreen for its diverse terrain and stunning natural beauty. Runners often highlight the extensive trail network, the refreshing cooler temperatures at higher elevations, and the breathtaking views of the Blue Ridge Mountains. The variety of routes, from challenging climbs to more moderate forest paths, is also a common positive remark.
Absolutely. If you're looking for a challenging workout, routes like The Priest loop from Three Ridges Wilderness are ideal. This 14.1 km trail features over 930 meters of elevation gain, providing a strenuous and rewarding experience through wilderness areas.
Wintergreen is an outdoor enthusiast's paradise. After your run, you can explore other activities at the Discovery Ridge Adventure Center, which offers ziplining and other family-friendly options. The region is also home to numerous wineries and breweries, perfect for relaxing and enjoying local flavors amidst beautiful scenery.


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