Woodside is a small incorporated town in San Mateo County on the San Francisco Peninsula. Horses are very much a part of the local culture there, and numerous residents tend to their horses in local stables. Consequently, the town government actually maintains a significant network of horse trails. Much of Woodside is forested with redwoods and Douglas Firs dominating in the western hills and Eucalyptus in the lower areas. San Francisco Bay lies to the east, while the Pacific Ocean beaches lie to the west. The Santa Cruz mountains separate Woodside from the ocean and extend down to Monterey Bay about 40 miles south. Hills and mountains between Woodside and the Pacific coast make fog far less prevalent than in nearby San Francisco.
Adjacent cities are San Mateo County neighbors and San Francisco Peninsula cities San Carlos, Redwood City, Portola Valley, Menlo Park, and Atherton. The town ranks among the wealthiest in the United States, and its population as per the 2010 US Census registered as 5,287. There were 5,510 residents as of a 2018 count. According to the United States Census Bureau, Woodside’s area totals 11.7 square land miles. As is true of most of the California coastal areas, and indeed much of the San Francisco Peninsula, the climate in Woodside is usually mild throughout most of the year.
Woodside is very popular with local cyclists and draws them in large number on the weekends. The Tour of California bicycle race includes several roads along and adjacent to CA-84 and Skyline Boulevard. Additionally, home to a number of open space preserves, Woodside boasts of 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 along Skyline Boulevard. “Filoli” is another Woodside phenomenon that was designed by California architect Willis Polk. This Georgian Revival mansion, which is surrounded by 16 acres of formal gardens and over 600 acres of woods, was built for William B. Bourn II between 1915 and 1917. Its reflecting pools, formal gardens, arbors, and shady walks were all planned to blend harmoniously with the nearby San Andreas hills. The spectacular grounds present a hallmark of garden landscape design, breathtaking in scale and displaying the diversity of California flora.
Woodside’s intentionally small business district includes: several restaurants, a “boutique” grocery store, a saloon, various goods and supply stores, a cleaner, and a post office. The “Village Pub”, “Alice’s”, and “Buck’s” are all renowned eateries and known to Silicon Valley entrepreneurs as locations where VC investment deals are often made.
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