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Skull Hollow Trailhead

Skull Hollow Trailhead, north of Redmond, OR, is the gateway to fabulous spring and fall riding. The trailhead has been enlarged and renovated, with a toilet and dedicated parking for horse trailers.  Two fun loops depart from the trailhead:  the Skull Hollow Loop and the Pine Ridge Loop.

Skull Hollow Trailhead

These loops use parts of the Cole Loop, a long-distance endurance trail, and connect with dirt roads to create shorter routes for day rides.

Both trails feature excellent tread in the shoulder seasons, and the spring wildflowers are stunning.

Skull Hollow Trailhead

The Riding

Skull Hollow Loop circles Gray Butte, a 5,108-foot cinder cone whose juniper- and sagebrush-covered flanks offer panoramic views of the snow-capped Cascades and the Crooked River Grassland.

Skull Hollow Trailhead

Skull Hollow Loop is 9 miles long, running on the Cole Loop and Gray Butte Trails and circling back to the trailhead along a dirt road.

Skull Hollow Trailhead

Pine Ridge Loop is an 8-mile ride.  It circles its namesake butte on the Cole Loop Trail and connects back to the trailhead via dirt and gravel roads.

Skull Hollow Trailhead

Both trails pass the historic McCoin orchard, the site of an old homestead.  The house is long gone, but the poplar trees and apple orchards remain.

Skull Hollow Trailhead

You are likely to encounter cattle and mountain bike riders on sections of these trails, so keep an eye out. But mostly, you will enjoy the incredible views, well-maintained trails, and spring wildflowers. Give the trails out of Skull Hollow Trailhead a try. You'll enjoy them!

More Information

Learn more about the Skull Hollow and Pine Ridge Loops in Riding Central Oregon Horse Trails, by Kim McCarrel, available at Central Oregon Horse Trails

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