Cowles Mountain & Pyles Peak

With “May Grey” in full force, I figured an early morning hike up Cowles Mountain, and then over to Pyles Peak would be a good choice. I needed to photograph the new summit marker that now sits atop Pyles Peak, and having a nice layer of clouds to keep the sun away sounded perfect. Since Covid-19 is still an actual issue, I opted not to take the shorter (and generally crowded) route up from Golfcrest to the summit to Cowles. Instead, I planned to either take the Barker Way route or the Big Rock route. In the end, I settled on the Barker Way route, mostly since it was a bit shorter than the Big Rock route. I found a spot on the street near the trailhead, grabbed my gear, and set off.

I actually had another choice to make almost immediately—do I take the service road all the way to the summit of Cowles, or do I take the trail to my left? The trail won the coin toss. There was no actual coin tossing, as trails will almost always win for me. The trail worked its way up the south side of Cowles, passing through the chaparral. Occasional steps helped lessen the grade as I kept climbing. I passed a connector trail that I could take to rejoin the service road, but I kept going, as there was another one closer to the summit that I planned to take. The trail I was on would actually connect with the route up from Golfcrest, and I had no desire to do that. From there I followed the service road to the summit of Cowles. I had never been on the service road, and was surprised at how steep it was.

At the summit I grabbed a quick photo of the marker and continued on. The marine layer hid much of the view, plus I still had another 1.5 miles to the summit of Pyles. 

I worked my way down the trail, losing about 300 feet of elevation before making a small climb and then more descent. Finally, I reached the start of the climb to the other summit. Once I reached it, two other hikers were taking a break here. I was on a work call, so I couldn’t stop and chat. I photographed the new marker and began back down.

The towers atop Cowles loomed to the south and I climbed back toward them. So far my neck, which had been giving me issues, was feeling ok. Once back at the Cowles summit, I snapped a few more photos. In case you are wondering, crossing back over a summit does not count as a new ascent.

I followed the service road back toward the connector, but instead of completely retracing my route, I opted to stay on the service road all the way down. Once back at the car I tossed my gear in and headed home. The peacefulness of the hike let me explore some ideas around a new interface design I am creating at work. Sometimes it is best to step away from the screens to give yourself some time to focus. I logged my hike at 5.76 miles in 2:39 and over 1,790 feet of net elevation gain. Now to finish that trail guide…


I am an avid peak bagger, sometimes backpacker, and former sea-kayaker living in San Diego. In 2019, I became the third person to complete the San Diego 100 Peak Challenge. Not stopping with that accomplishment, I set my sights on the harder San Diego Sierra Club 100 Peak list, which I completed in 2021. In addition, I have conquered several Six-Pack of Peaks challenges (SoCal, San Diego, and Arizona-Winter). Beyond attempting the San Diego Sierra Club 100 Peak list a second time, I am looking forward to exploring new summits and new adventures across the southwest. 

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