James "Sunny Jim" Rolph, at the wheel, summered in what is now Portola Valley while he served five terms as mayor of San Francisco starting in 1912. He was elected governor of California in 1931.
He owned what is today the Pony Tracks Ranch as well as several thousand more acres.
In this photo, his wife is in the back seat at left. The Rolph children and the Pryor family of Menlo Park are also aboard the car.
(Photo courtesy Portola Valley Archives.)