The mountain is named after George A. Cowles, a 1870s-80s rancher and early businessperson in southwestern San Diego County. For many years Cowles Mountain was locally known as “S” Mountain. In 1931, 500 students from San Diego State University, painted a 400-foot-tall (120 m) letter “S” on the side of the mountain, after which it took on its popular name. In April 1942, during World War II, the local military ordered the S covered up for the sake of national security. After the war the painting tradition was resurrected.
In the 1970s, the annual repainting tradition was ceased for environmental and habitat protection, but suffered a brief resurgence in the late 1980s. The “S” has not been repainted for nearly three decades.
Personal Experience: If you decide to do this hike at night make sure to have a flashlight or headlamp and good shoes! This is a jagged trail and it’s easy to twist your ankle! I speak from experience. With that aside, night hikes are so special. Besides the fact that you have the entire mountain to yourself, those views at night are next level!
I want to give a shout out to Cowles Mtn. Coffee which is right across the street from the trailhead. The coffee and drinks are SUPER good here and they have a ton of healthy and unique options. The owner is such a sweetheart too. I love to stop by here if I’m in the area. They’re open 7:30am-2pm daily:
We headed out about 30 minutes before sunset. We probably should have started a little earlier, but it definitely made for less foot traffic!
There’s a little monument at the top:
The view at the top is other-worldly!
We came across a tarantula!!