Cowles Mountain is a prominent hill within the city limits of San Diego, California and also within Mission Trails Regional Park. The hill is named after George A. Cowles, an early ranching pioneer in San Diego County.

Its 1,592 foot (485m) summit is the highest point in the city of San Diego. The main trail to the summit is a popular hiking destination taking hundreds of people per day to a breath-taking 360 degree panorama of San Diego County. The hike to the top is 1.5 miles long and an elevation change of about 950 feet.

This trail is on the corner of Golfcrest Drive and Navajo Road. A much-less-used but maintained trail begins near the intersection of Boulder Lake Avenue and Barker way. This trail meets the main trail near the summit.

For many years Cowles Mountain was locally known as "S" Mountain. In 1931, 500 students from San Diego State University (SDSU) painted a 400 foot tall 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 discarded due to complaints from environmentalists but enjoyed a brief resurgence in the late 1980s.(see discussion page) In 1991 the "S" was the basis of a prank by Seniors from nearby Patrick Henry High School. Overnight, the "S" was closed into a "9" and a crude "1" was added next to it.

SDSU students eventually restored the "S" one last time. The mountain, except for marked trails, is now a protected area and the "S" has not been repainted for nearly two decades.

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