4.9
(6)
68
riders
5
rides
Touring cycling around Wintergreen traverses the Blue Ridge Mountains, characterized by significant elevation changes, dense forests, and scenic overlooks. The region features winding mountain roads and valleys, offering challenging climbs and descents. These routes navigate through varied terrain, including forested areas and open stretches with distant views. The area's landscape is defined by its mountainous terrain and numerous natural features.
Last updated: May 4, 2026
5.0
(1)
4
riders
72.1km
05:02
1,150m
1,150m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.7
(3)
5
riders
46.0km
03:21
990m
990m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
83.6km
05:52
1,520m
1,520m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
30.6km
02:43
700m
700m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
30.5km
03:01
670m
670m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.
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Bald Mountain is a 3250 ft high grassy peak with views of Saint’s Mary Wilderness. The bald is reached after 4.5 km of hiking and is a great place to rest and appreciate the expansive views. This is one of the best overlooks in the vicinity due to its wonderful views, so enjoy it! This bald is also not the most popular one in GWNF, so you might find some quietness there.
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At Milepost 13.1 on the Blue Ridge Parkway is the 3 Ridges Mountain Overlook. You are at an elevation of 2,800 feet at the overlook, but the highest summit you can see from here is 3,900 feet. The Appalachian Trail also crosses the road here, so it can be a sort of busy overlook at times.
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Ravens Roost Overlook is at Milepost 10.7 on the Blue Ridge Parkway and is one of the most popular overlooks in this part of Virginia. From an elevation of 3,200 feet, you can look down into the old farming valley and along mountain ridges running perpendicular to the parkway.
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Ravens Roost Overlook is at Milepost 10.7 on the Blue Ridge Parkway and is one of the most popular overlooks in this part of Virginia. From an elevation of 3,200 feet, you can look down into the old farming valley and along mountain ridges running perpendicular to the parkway.
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The Sherando Lakes are commonly referred to as "the jewels of the Blue Ridge Mountains." The lower lake is much bigger than the upper lake, but both have their draws. There are a lot of recreational amenities surrounding the lakes, and there are also a number of different hiking trails that you can connect to for longer day hikes and overnight trips.
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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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Located at Milepost 8.8 on the Blue Ridge Parkway, Greenstone Overlook peers over the foothills of Virginia. The overlook is situated at exactly 3,000 feet on an outcrop of the Catoctin Greenstone. The rock in the area was formed from an ancient lava flow, which is unique to this particular area of Virginia.
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Leave your bike at the start of the trail and hike 1.2 miles (1.9 km) to the magnificent White Rock Falls. The views are just as impressive as the falls.
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Touring cycling routes in Wintergreen are predominantly challenging, characterized by significant elevation changes through the Blue Ridge Mountains. All six routes listed are rated as difficult, making them suitable for experienced cyclists seeking a strenuous ride.
Yes, many of the touring cycling routes in Wintergreen are designed as loops. For example, the Three Ridges Mountain Overlook – Wigwam Falls loop from Wintergreen and the Ravens Roost Overlook – Three Ridges Mountain Overlook loop from Dripping Rock are both popular circular options.
The touring cycling routes in Wintergreen vary in length and duration. You can find routes like the Trout Pond loop from Crabtree Falls Campgound, which is about 30.5 km (19 miles) and takes around 2 hours 42 minutes. Longer options include the Three Ridges Mountain Overlook – Wigwam Falls loop from Wintergreen, spanning 114 km (70.8 miles) and requiring approximately 10 hours to complete.
Given the mountainous terrain and significant elevation changes, the touring cycling routes around Wintergreen are generally rated as difficult. There are no routes specifically categorized as easy or moderate for beginners or young families within this selection. These trails are best suited for experienced cyclists.
Many routes in Wintergreen feature stunning scenic overlooks. The Ravens Roost Overlook – Three Ridges Mountain Overlook loop from Dripping Rock is known for extensive views, while the Ravens Roost Overlook – Shenandoah Valley loop from Wintergreen offers valley vistas. You can also find viewpoints like Ravens Roost Overlook and Three Ridges Mountain Overlook along these routes.
Beyond the scenic mountain views, you can discover several natural attractions. Highlights include waterfalls like Shamokin Falls and White Rock Falls. Other points of interest include Humpback Rocks Trail and various viewpoints such as Rockfish Valley Overlook.
The touring cycling routes in Wintergreen are highly rated by the komoot community, with an average score of 4.8 stars from multiple reviews. Cyclists often praise the challenging mountainous terrain, dense woodlands, and the numerous scenic overlooks that provide rewarding views throughout the rides.
While not explicitly stated in the route data, the Blue Ridge Mountains region, including Wintergreen, generally offers pleasant touring cycling conditions in spring and fall. Spring brings blooming foliage, and fall showcases vibrant autumn colors. Summer can be warm, and winter may present icy conditions at higher elevations, making these seasons more challenging.
The touring cycling routes in Wintergreen traverse mountainous and forested areas. While specific cafes or pubs directly on the routes are not detailed, it's advisable to carry sufficient water and snacks. You may find options in nearby towns or at the Wintergreen Resort itself, but plan your stops carefully, especially on longer rides.
Wintergreen, located in the Blue Ridge Mountains, experiences varied weather. Expect cooler temperatures at higher elevations, and conditions can change rapidly. Be prepared for potential fog, rain, or strong winds, especially during spring and fall. Always check the local forecast before heading out.
While specific parking details for each route are not provided, many touring cycling routes in Wintergreen originate from accessible points like Wintergreen Resort or nearby towns. For example, the Ravens Roost Overlook – Three Ridges Mountain Overlook loop starts near Dripping Rock, and the Trout Pond loop begins from Crabtree Falls Campground, suggesting parking availability at these locations.
All touring cycling routes in Wintergreen are rated as difficult, offering significant challenges for experienced cyclists. The Three Ridges Mountain Overlook – Wigwam Falls loop from Wintergreen is particularly demanding with over 2800 meters of elevation gain over 114 km. The Trout Pond – Fork Mountain Overlook loop from South Fork Rockfish River also presents a substantial challenge with nearly 1500 meters of ascent.


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