Kennywood Trail is considered by most locals as the best trail at WOP. It is a fast trail that has the most technical obstacles including two man-made drop-offs and multiple natural obstacles known as the"Pittsburgh Potholes."
Kennywood is a bi-directional trail but is recommend from East to West to utilize the man-made drops. The first wooden drop is about 1' tall and allows straightforward entry and descent. The second drop is stone and demands more technical skills. It requires a sharp turn to line up the drop and a sharp angle to avoid a tree/root on the descent. As with all obstacles in WOP, there are easy bypasses nearby.
The Pittsburgh Potholes are natural obstacles made by years of underground mining. They are up to 8' diameter and 5' deep. You can ride around the rim or ride right through them.