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Fun yet challenging
This trail is well-worn and well-used by both hikers and bikers. As you continue what I call a counter-clockwise traverse of the Pass Mountain Loop trail, you'll enjoy this walk as it hugs the eastern slope of Pass Mountain. The trail begins a fairly steep incline toward the point that it flattens out at the "pass". Once you reach this point, this is where you'll leave the trail and begin the ascent of Pass Mountain Peak. There is no trail here - you must find your own way up, but it is not too difficult. I chose to work my way up the spine of the mountain, constantly climbing and gaining elevation. Only at one point did I actually have to use some hands to help pull myself up a crack in the rocks to keep going.
You reach one summit that is marked with a large cairn, but you can see that the true summit is just a short distance further to the west. Continuing onward toward the true summit is very rewarding. The 360-degree view is stunning and it is exciting to stand on the rock that represents the highest point within Usery Park. Be sure to sign the logbook contained in the green metal box that is anchored to a rock within sight of the top rock. Stop to enjoy the view. From here, just keep heading southward along the ridgeline. There is evidence of foot traffic along this portion from Pass Mountain Peak to the intersection with the wind cave "extended" trail. (I call it "extended" because if you hike up the Wind Cave trail from the Usery Park parking lot, you will reach the wind cave and then there is a sign that says something like "beyond this point trail is not maintained".)
All in all, a great hike with wonderful views, plenty of solitude on top. For me, this hike took four hours - moving for three out of the four and resting one hour.
Check out the Official Route and Triplogs.