Skyliner-Whoops-Jim’s-Phil’s

After leaving the trailhead you begin a meandering climb for a little longer than two miles. You know you’ve reached the top when you get to the wooden bench and the kiosk with information about the Whoops Trail. This is a downhill-only section of trail that is also just over two miles to the bottom. This is a progressive trail, heavily manipulated by the hands of dedicated builders. Jumps, berms, rollers, table tops and hips, all the way down the hill. When you reach the Forest Service road and see signs for Ben’s Trail, I prefer to head right, up the road for approximately 1/4 mile until reaching a left-hand turn onto Jim’s Trail. From here you begin working your way down again. Jim’s becomes Phil’s Trail, and anyone familiar with the riding in Bend has heard of or ridden Phil’s; not that it’s the most challenging or technical trail, but it’s a local/regional legend, the first trail to really bring mountain biking to the area. More descending as you work your way back to the Phil’s trailhead. From here you can begin to climb back out toward Skyliner via Ben’s Trail or Kent’s Trail.

Seasons: Spring – Fall