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San Mateo County/Silicon Valley

Home to many of Silicon Valley’s CEOs and executives, Woodside is among the wealthiest small towns in the United States. It is adjacent to the campus of Stanford University, which is east of the town and is known for its equestrian community. The intentionally small business district includes a few restaurants, the famous Roberts Market grocery store, a saloon, a horse tack store and a postal office.

Woodside is also home to a number of open space preserves, including Purisima Open Space, where both horseback riding and bicycling are allowed. Horses are part of the local culture and numerous residents keep horses. The town is also popular among local cyclists with popular road cycling routes such as Old La Honda Road, King's Mountain Road, Cañada Road, Southgate Drive, Skyline Boulevard and Highway 84. Click here to learn more about Woodside.