Shortly after crossing the bridge near the corral in Wilder Ranch you will come to a crossroads where Engelsman’s Loop and Cowboy Trail meet. Engelsman’s Loop is to your left and Cowboy Trail is to your immediate right. Just look for the trail marker to know you are on the right trail.
Cowboy Trail starts off level and then gradually ascends to overlook Wilder Ranch and the Pacific Ocean. The view at this point is pretty amazing! The trail winds through open grassy plains with nearby farmland. The trail keeps ascending until it takes a sharp left once you reach a private property fence.
The trail then quickly descends back into the cover of oak trees through a series of switchbacks. This section of trail is fairly shaded and eventually will wind back to the bridge starting point.
This is a fun little trail with great views that is easy to complete. It's a nice way to round off your visit to Wilder Ranch.