The best road cycling routes around Sherando
5.0
(8)
393
riders
35
rides
Last updated: November 7, 2025
5.0
(1)
24
riders
1. Afton Overlook to Ravens Roost Overlook — Blue Ridge Parkway
34.8km
01:59
780m
780m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
19
riders
2. Shenandoah Valley – Blue Ridge Parkway
70.1km
03:36
1,130m
1,130m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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7
riders
3. Ravens Roost Overlook to Boston Knob Overlook — Blue Ridge Parkway
90.4km
04:54
1,820m
1,820m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
4. Ravens Roost Overlook – Shenandoah Valley loop from Sherando
154km
08:21
3,120m
3,110m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
5. Rockfish Valley Overlook – Afton Overlook loop from Wintergreen
52.5km
03:20
590m
590m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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