At 5,910 feet, Pilot Rock is one of the must see places in Southern Oregon. Pilot Rock is one of the most uniquely shaped, and prominent, land features in the Siskiyou Mountains southeast of Ashland, Oregon. It has been known by that name since pioneer days, when travelers crossing the Siskiyou Pass between Oregon and California used it as a guide. The hike to the base of the rock is easy and fun, with views up across the Shasta Valley to Mount Shasta. The climb starts off with a short hike to a small but daunting little climb or scramble. But be strong the climb is worse then it looks and the views on top are amazing.