Woodside residents value secluded outdoor living while enjoying a strong sense of community. Separated from the ocean by the Santa Cruz Mountains, towering redwoods dominate its western hills, with oaks and eucalyptus in the lower areas. Residents value its privacy, access to nature, large parcels of land, and diverse architecture.
Settlers arrived in the early nineteenth century to log the rich stands of redwoods. Later, prosperous San Francisco families built country estates in Woodside with regular stagecoach service to San Francisco established in 1852. Farms, small cattle ranches, and vineyards replaced the sawmills and its hillsides and steep ravines are now filled with vines, tended by notable winemakers such as Thomas Fogarty. Rapid growth after World War II alarmed local residents, who feared that their rural haven would be transformed into an urban area. Residents incorporated in 1956 to retain local control and stop urbanization.
This town of just over 5,000 enjoys a rural lifestyle with local trails, horse properties, open space preserves, and artists’ colony and summer jazz at the beautiful Filoli Garden. Popular cycling routes draw cyclists in droves on the weekends along Cañada Road, Old La Honda Road, Kings Mountain Road, Skyline Boulevard, and Highway 84. Woodside is also home to several open space preserves, including Purisima Open Space, Huddart County Park, the Phleger Estate, and Skeggs Point.
The small business district includes Roberts Market, a hardware and horse tack store, and a few restaurants, including the iconic Buck’s of Woodside, where many venture capital deals have been inked. Woodside is home to a mix of Silicon Valley movers and shakers – CEOs and venture capitalists, as well as famed musicians and artists.