Woodside

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.

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 quite 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 (which is part of the Midpeninsula Regional Open Space), where both horseback riding and bicycling is allowed. For mountain biking, the famous Skeggs Point is located in Woodside along Skyline Boulevard. There is also an extensive archery course maintained by volunteers in the adjacent Huddart County Park.