Woodside, California Has Kept Silicon Valley's Fortunes on Horseback for Decades

Woodside sits close enough to Sand Hill Road, the stretch of Menlo Park lined with the venture capital firms that fund much of Silicon Valley, that the two are effectively neighbours. The town itself looks nothing like it: redwood-shaded lanes, working horse properties and a strict large-lot zoning code that has kept much of Woodside from ever being subdivided into the kind of dense housing found lower down the peninsula.

From sawmill town to estate country

Woodside's history starts with redwood: in the 1830s it was a logging settlement supplying timber to San Francisco, before the forests thinned and the land was gradually turned over to ranches and vineyards. The rural infrastructure that supported that earlier economy, wide lots, horse trails and minimal street lighting, was never fully built over, and the town's current zoning rules have deliberately preserved it since.

View on Google Maps →

An equestrian culture that never left

Woodside maintains a network of public horse trails through its hills, and a meaningful share of its large properties are still built or bought with stables and paddocks as standard, not an add-on. That equestrian identity, more than its wealth, is what residents tend to cite as the thing that actually distinguishes the town from equally affluent parts of the peninsula.

The estate that made the point

Oracle co-founder Larry Ellison has held a Woodside compound built around a recreation of a 16th-century Japanese estate, complete with a converted barn and grounds landscaped over decades, alongside a separate multi-acre property he bought largely to house horses. The scale of the project became one of the more widely reported examples of what a Woodside estate can turn into once money stops being the constraint.

Still a village at its centre

Despite the estates around it, the town's centre remains modest: a scattering of shops, a historic general store dating to the nineteenth century, and little else built up in a way that would suggest the wealth surrounding it. That contrast, a working village front with country estates just out of sight, is largely the point.

Traveller tips

• San Francisco International and San Jose International airports are both roughly 45 minutes away by car.
• Woodside has no hotels of note; most visitors base themselves in Palo Alto or Menlo Park and drive in.
• Public horse trails wind through Wunderlich County Park and connect into much of the surrounding open space; check trail maps before setting out.
• Properties here are private; the estates themselves are not open to visitors and are best appreciated from public roads and trails rather than sought out directly.