The Woodside area was originally home to natives belonging to the Ohlone tribe. In 1769, led by Gaspar de Portolá, Spanish explorers searching for San Francisco Bay camped at a site near Woodside.
Woodside is located on the Rancho Cañada de Raymundo Mexican Land grant. Woodside is said to be the oldest English-speaking settlement in the southern part of the San Francisco Peninsula. The first English-speaking settlers arrived in the early 19th century to log the rich stands of redwoods. Charles Brown constructed the first sawmill in Woodside on his Mountain Home Ranch around 1838. His adobe house, built in 1839, still stands today. By mid-century, the Woodside area had a dozen mills producing building materials for a booming San Francisco.
Today, 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; 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.
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Updated: 20th August, 2019 1:27 AM.