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Winchester

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Recommended Routes in Winchester - 1

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Favorite Challenging rock garden on the way down the hill.
Difficult

Rolling Ridge

11.5 mi 18.5 km 1,309' Up 399.04 m Up 1,308' Down 398.68 m Down

Berryville, VA

Winchester Biking

  • 16 Miles 25 Kilometers of Trail
  • 1 Recommended Route
  • 1 Easy Trail Easy Trails
  • 3 Intermediate Trails Intermediate Trails
  • 0 Difficult Trails Difficult Trails
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Areas Within Winchester

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Trails in Winchester - 3

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1.5 mi 2.5 km #1Ridge to River Trail
Intermediate
Berryville, VA
Intermediate
Berryville, VA
1.7 mi 2.8 km #2Cart Path
Easy
Berryville, VA
Easy
Berryville, VA
0.9 mi 1.4 km #3Cart Path
Intermediate/Difficult
Berryville, VA
Intermediate/Difficult
Berryville, VA

Photos of Winchester - 12

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Info Booth & Map.
Jul 21, 2021 near Berryville, VA
'Walk Your Bike' creek crossing
Jul 21, 2021 near Berryville, VA
Info booth and bridge.
Jul 21, 2021 near Berryville, VA
Paved path towards the entrance of the trail. You can go left or right, but not on the gravel road.
Jul 21, 2021 near Berryville, VA
Parking lot.
Jul 21, 2021 near Berryville, VA
University Campus.
Jul 21, 2021 near Berryville, VA
A waterfall cascades above the crossing over Rocky Branch. There is a trail that goes upstream to explore more.
Mar 12, 2017 near Berryville, VA
This stream crossing is rideable and a fun challenge because it is steep and slick.
Mar 12, 2017 near Berryville, VA
Rolling Ridge Entrance.
Jul 21, 2021 near Berryville, VA
Turn off the paved path to the trail. Follow the sign.
Jul 21, 2021 near Berryville, VA
Building at the park entrance
Mar 30, 2021 near Berryville, VA
This is the turnoff from the Cart Path Connector onto the Ridge to River Trail. If you start going up a big hill, you went too far!
Mar 12, 2017 near Berryville, VA