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Rolling Ridge Lollipop

 4.2 (9)

11.9 Miles 19.1 Kilometers



1,194' 364 m


-1,194' -364 m



Avg Grade (2°)


Max Grade (17°)

1,309' 399 m


375' 114 m


Shared By Mark Hoyle


Minor Issues 38 days ago
Muddy - Lead in trail from the park is super muddy and completely washed out in some places. History

Getting forecast...

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

Mark Hoyle

Dogs Leashed

Features -none-


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.
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.

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.


Local Club: MTB Loco

Land Manager: Rolling Ridge Retreat Center

Jun 22, 2018: Ghost Pipes

Apr 16, 2018: Breaking the Spell

Apr 10, 2018: I am so distant from the hope of myself…

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Your Check-Ins


Jun 8, 2018
Ted Angle
There is a lot of erosion/washouts on the lead in and perimeter trail. This turned out to be a hike with occasional bike ride.
May 20, 2018
Dan Simpson
Holy rivers. Getting muddy and wet and a case of west Nile :) supper fun though
Apr 14, 2018
Dennis Throckmorton
Feb 3, 2018
Mad Cow
Great ride. Well marked. 12.4mi
Oct 1, 2017
Aaron Rogers
A few wrong turns and out to explore. 13.9mi
Sep 17, 2017
ydant ydant
It's a stretch to call it a MTB trail - more of a hiking trail that allows bikes - but it's doable. Plenty of very difficult climbs and rock sectio... 11.6mi
Aug 5, 2017
Aleks Racenis
fun trail. worth the climb
Jul 16, 2017
John Spindle Jr

Trail Ratings

  4.2 from 9 votes


  4.2 from 9 votes
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in Virginia


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4,960 Since Aug 31, 2016
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