Today, Woodside is among the wealthiest small

towns in the United States.

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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, and a post office. 

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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.

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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. 

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Woodside is home to a number of open space preserves, including the Purisima Open Space and many more located in Woodside along Skyline Boulevard.