Cowles Mountain (pronounced 'kohls') got its name from George A. Cowles, one of San Diego's early prominent ranching pioneers. George Cowles settled in the El Cajon valley in 1877. He purchased approximately 4,000 acres of land comprising two ranch sites about a mile apart; Woodside Ranch and Magnolia Ranch. He planted a variety of fruit trees, grapevines, olives, grains and potatoes. Cowles' products gained nationwide attention for San Diego's farming potential, particularly in fruits and vines. He also raised thoroughbred horses and cattle. The community that developed around his 'Woodside' ranch became known as Cowlestown. George Cowles died in 1887, leaving his estate to his widow Jennie. Jennie Cowles continued ranching into the 1890's. She married Milton Santee in 1890 and moved to the City of San Diego. Cowlestown officially became Santee in 1893, named for Jennie's second husband, a real estate developer.

Information from 'Cowles Mountain' written by Bill White, Mission Trails Regional Park Volunteer.