Woodside, California

Woodside is a small incorporated town in San Mateo County, California, United States, on the San Francisco Peninsula. It has a council–manager system of government. The population of the town was 5,287 at the 2010 census. Woodside is home to many horses and is among the wealthiest communities in the United States. 

Woodside is among the wealthiest small towns in the United States. The intentionally small business district includes: a few restaurants; a grocery store; a saloon; a hardware and horse tack store; a home and garden store; an Aveda hair salon; a cleaner; and a post office. Outside of the business district are the Stillheart Institute educational event center, Skywood Trading Post and the Mountain Terrace event center.

Town restaurants include the Michelin starred Village Pub, Buck's of Woodside restaurant, known among Silicon Valley entrepreneurs as the location where many VC investment deals have been signed and the Firehouse Bistro.

Horses are part of the local culture. Numerous residents keep horses and the town government maintains a network of horse trails. Some resident's homes are even considered farms. The town is also popular among local cyclists and draws them in large numbers on weekends. The most popular road cycling routes include Old La Honda Road, King's Mountain Road, Cañada Road, Southgate Drive, Skyline Boulevard and Highway 84. The Tour of California bicycle race includes several roads along and adjacent to CA-84 and Skyline Boulevard.

Woodside is home to a number of open space preserves, including the Purisima Open Space (part of the Midpeninsula Regional Open Space), where both horseback riding and bicycling are allowed. For mountain biking, the famous Skeggs Point is located in Woodside along Skyline Boulevard.