With its roots in the California Gold Rush, Woodside is a place of legend and mystique. Originally a vast Spanish Rancho, Woodside was one of the sources of lumber that supplied the building boom of San Francisco, located 30 miles to the North. Today, Woodside stands as one of the wealthiest communities in the country, characterized by quiet, rustic luxury. It is noted for its country estates nestled on wooded acreage. In Woodside, tranquil lanes, most barely wide enough for two cars, meander through canopies of oaks and redwoods. The estates, usually secluded from the road and secured behind stone walls and iron gates, are rarely seen. Private vineyards, olive orchards, pastures, corrals, and weathered barns dot the gently rolling terrain. While Woodside boasts several grand estate homes such as the famous Filoli Estate, renowned for its appearance in the television show Dynasty, and the Buck Estate, a colossal Tudor/Gothic revival, the homes in Woodside are most often rustic interpretations of Craftsman, farmhouse, and early California styles. This includes several landmark haciendas, ranches, and contemporaries designed by noted architects like Cliff May, Gardner Daly, and William Wurster.
Reflecting the laid-back culture of Woodside is the charming downtown, home to institutions like the Pioneer Saloon, Bucks of Woodside restaurant, the Michelin-awarded Village Pub, Roberts’ Market, Roberts’ Hardware and Tack, and other small businesses catering to the locals. Outside the business district, you’ll find the Skywood Trading Post, Bella Vista Restaurant, the Mountain House, and Alice’s Restaurant, made famous by the Arlo Guthrie song.
Horses play a significant role in Woodside’s culture, with the breeding of Thoroughbred, carriage, and steeplechase horses. Well-used horse trails meander through Woodside, with hitching posts and watering troughs in front of the town hall and many businesses. With only one thoroughfare, Woodside is very bicycle-friendly, with cyclists almost as plentiful as cars.
Within or near Woodside, thousands of acres of open space abound, including hiking trails, forests, meadows, creeks, and mountain ridges, inhabited by a multitude of deer, coyotes, bobcats, squirrels, and other wildlife. Occasionally, a mountain lion is spotted, while eagles and falcons can be seen riding the air currents.
Discreetly headquartered in Woodside are international investment capital firms such as Fisher Investments, Crosspoint Ventures, and Tanaya Capital. Notable residents include Larry Ellison, the founder of Oracle; Tom Siebel, the founder of Siebel Systems; Scott Cook, the founder of Intuit; and producer David E. Kelly. Steve Jobs, the founder of Apple, is building a new home on several acres in Woodside. Music stars like Tom Fogarty, Joan Baez, and Neil Young also call Woodside home. In addition, Woodside boasts a thriving artist colony, with notable landscape artists such as Jim Caldwell, Nancy Meze, and Gil Draper among many others, inspired by the spectacular beauty of Woodside’s oak and redwood-covered hillsides and mountains.
Reflecting the romance of the Old West and the American spirit, Woodside is a step back to an earlier, simpler time—a laid-back retreat from the intensity and pace of nearby Silicon Valley. It is a place truly unique in the world.
The history of Woodside
Nestled within the historical tapestry of California’s past, Woodside, with its origins tracing back to the Gold Rush era, has evolved into a prestigious residential enclave renowned for its opulent living and unwavering dedication to preserving its natural beauty.
Under Spanish and then Mexican rule, Woodside’s land was part of extensive land grants, primarily used for cattle grazing. The transition to American ownership occurred with the Treaty of Guadalupe Hidalgo in 1848, marking California’s incorporation into the United States.
The California Gold Rush of 1848-1855 propelled Woodside into the spotlight as a crucial lumber source for San Francisco’s construction boom. It was officially founded in 1849, named for its abundant redwood trees. As the 19th century progressed, Woodside transitioned to an agricultural community known for its orchards, vineyards, and elegant estates. In the 20th century, it attracted prominent residents, including tech leaders and celebrities, becoming one of the nation’s wealthiest communities. Woodside’s commitment to preserving its natural environment and rural charm sets it apart as a sought-after residential destination.
