Starting from a small clearing off of FS Road 340, the Woodenshoe Trail (#165) descends through a forest of pine, aspen, and oak. After the first mile, hikers enter the Dark Canyon Wilderness, and soon reach the southern part of Woodenshoe Canyon. The trail then winds its way to the bottom of the canyon through a section of low cliffs. As the trail turns to the northwest, hikers can appreciate the view of Cherry Canyon behind them. Not too far away is a ruin worth exploring, and this can be a good spot to turn around for a shorter hike.