Rolling Ridge Lollipop

 3 votes
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Featured Ride

11.9 Miles 19.1 Kilometers



1,194' 364 m


-1,194' -364 m


1,309' 399 m


375' 114 m



Avg Grade (2°)


Max Grade (17°)

All Clear

70 days agoUpdate

This loop starts at the Shenandoah University Cool Springs campus off VA Route 7.

Mark Hoyle


Hunting season, closed: October 1-December 31. Please do not ride here at that time as the property is being used by hunters to help control the deer population.
This route just gets better every time you ride it. The trail is ridiculously steep in places when climbing, but features great flow across the ridge and downhill. Be sure to ride this loop counter-clockwise. There is easy access and parking at the Shenandoah University Cool Springs campus parking lot.
Dogs: Leashed

Need to Know

Be sure to sign in at the kiosk about 3/4 of the way through the ride and also you MUST fill out a waiver on the Rolling Ridge site and submit.

Complete and return the completed waiver to


This route has rocks, loads of climbing, and winds tightly between trees with moves that seem impossible (but are). This trail is 30 minutes from Winchester and Leesburg and has it all. Ride in from Shenandoah University property off Route 7 and follow the Cart Path Connector to the cut off for the Ridge to River Trail that leads into the retreat.

The Ridge to River Trail is at the end of the Shenandoah property and is about a 4' wide mowed pathway branching off to the left. It is well maintained and leads into the forest on a very well-used doubletrack trail. If you start climbing up a concrete steep ramp on the Shenandoah property, you've missed the turn off.

Follow the doubletrack, cross the creek and continue straight ahead. You can walk up the creek for some beautiful waterfalls, but I'm not sure if that trail connects to anything on the other side, though the track goes up the creek a few hundred feet.

The doubletrack now turns into more of a dirt road and makes a right turn uphill and begins the climb. The climb on the road is steep, but rideable. When you come to a trail coming in on the left, it will have a sign for the Perimeter Trail. This is where you'll end up after riding the Perimeter Trail as described on that trail page.

The Perimeter Trail loop is challenging, but well worthwhile for riders in the area. Once you've completed a full loop, you'll return to your starting point at an intersection with the Ridge to River Trail, and will take that trail to return to the Cart Path Connector which will eventually return you to the trailhead and your car.

History & Background

Great route to ride in a remote setting. Please respect any pedestrians you may encounter since visitors at this retreat are there for peace and renewal. We are being allowed to ride these trails and must respect the landowners to maintain the access. Visit their website to see what it is all about.


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in Virginia


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All Clear 70 days ago
Mostly Dry
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