Portola Valley, CA

Portola Valley is a small, affluent town in San Mateo County, tucked into the foothills of the Santa Cruz Mountains. It is named for Gaspar de Portola, whose expedition explored the San Francisco Peninsula in 1769. The town is known for its extensive trail network, including routes maintained locally and connections to Windy Hill Open Space Preserve. Our Lady of the Wayside Church, built in 1912, adds a historic landmark note. Portola Valley feels rural and wooded despite being deep in Silicon Valley's orbit.