Cycling in Winchester
Discover a map of 27 cycling routes and bike trails near Winchester, created by our community.
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Get to know Winchester
Find the right bike route for you through Winchester, where we've got 27 cycle routes to explore.
1,658 km
Tracked distance
27
Cycle routes
26,203
Population
Community
Most active users in Winchester
From our community
The best bike routes in and around Winchester
FIRST 14 MILE RIDE IN BLUE RIDGE MTNS VIRGINIA
Cycling route in Winchester, Virginia, United States
- 48.7 km
- Distance
- 200 m
- Ascent
- 205 m
- Descent
Rhona to Jeff/Louisa
Cycling route in Winchester, Virginia, United States
- 27.9 km
- Distance
- 266 m
- Ascent
- 235 m
- Descent
winchester walk
Cycling route in Winchester, Virginia, United States
- 9 km
- Distance
- 97 m
- Ascent
- 72 m
- Descent
WINCHESTER NORTH
Cycling route in Winchester, Virginia, United States
- 11.4 km
- Distance
- 100 m
- Ascent
- 80 m
- Descent
Discover more routes
Vineyards and Dog Legs- Distance
- 58.5 km
- Ascent
- 302 m
- Descent
- 297 m
- Location
- Winchester, Virginia, United States
Winchester to Washington DC- Distance
- 128.5 km
- Ascent
- 514 m
- Descent
- 720 m
- Location
- Winchester, Virginia, United States
Restful route in Stephenson- Distance
- 13.5 km
- Ascent
- 680 m
- Descent
- 678 m
- Location
- Winchester, Virginia, United States
Geocache 1.0- Distance
- 15 km
- Ascent
- 86 m
- Descent
- 87 m
- Location
- Winchester, Virginia, United States
Long ride through Winchester- Distance
- 73.5 km
- Ascent
- 338 m
- Descent
- 338 m
- Location
- Winchester, Virginia, United States
Lengthy ride through Winchester- Distance
- 60.6 km
- Ascent
- 252 m
- Descent
- 236 m
- Location
- Winchester, Virginia, United States
443 Millwood Ave, Winchester to 425 Millwood Ave, Winchester- Distance
- 0.8 km
- Ascent
- 0 m
- Descent
- 0 m
- Location
- Winchester, Virginia, United States
Berryville Pike 1347, Winchester to Hartman Drive 501, Harrisonburg- Distance
- 121.9 km
- Ascent
- 3,240 m
- Descent
- 3,033 m
- Location
- Winchester, Virginia, United States