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Woodside sits in the hills of San Mateo County on the San Francisco Peninsula, a small and quietly affluent town that has long occupied an unusual position in California life. It is simultaneously one of the wealthiest communities in the United States and one of the most deliberately low-key, a place where equestrian trails thread between redwood groves and the main street retains the unhurried character of a rural village despite its proximity to Silicon Valley. The town's identity is shaped as much by what it has chosen not to become as by what it is.

The surrounding landscape is the defining fact of Woodside. The Santa Cruz Mountains rise to the west, and the town sits at their eastern foothills, giving residents and visitors access to Huddart County Park and Wunderlich County Park, both of which preserve substantial stands of second-growth coast redwood. These parks draw hikers and equestrians from across the Bay Area, and the network of trails connecting them reflects the town's long-standing commitment to open space. Horses are a serious matter here: Woodside has more horses per capita than almost any other incorporated place in California, and the culture around riding, stabling, and trail access shapes local planning decisions in ways that would be unusual almost anywhere else.