Woodside, CA Area Guide

Long before Silicon Valley existed, the land that became Woodside was shaped by Spanish exploration and Mexican land grants. In 1769 Gaspar de Portola led an expedition that camped near this site, and by 1840 the territory was part of Rancho Canada de Raymundo, a Mexican land grant later conveyed to John Coppinger in 1841, making Woodside one of the earliest English-speaking settlements on the southern San Francisco Peninsula.

The town grew as loggers moved in to harvest the abundant redwood stands, and Charles Brown established the first sawmill in the area, setting off a milling era that gave the place both its economy and its name. Those old-growth redwoods were never fully erased, and their descendants still tower over the preserves and parks that residents hike and ride through today.

Dining in Woodside is intentionally spare, concentrated along a small stretch of Woodside Road rather than spread across a commercial district. The Village Pub has a Michelin-starred menu of contemporary American cooking and an extensive wine list. Buck's of Woodside is a casual, decades-old landmark known for its wildly eclectic decor and a long history as an informal gathering spot for Silicon Valley deal-making.

For everyday needs, Roberts Market operates a well-stocked deli and prepared foods counter that fills in the gaps. Residents who want broader options typically make the short drive to Palo Alto or Redwood City, where the dining range widens considerably.

Getting around Woodside means getting behind the wheel. Woodside Road connects directly to Interstate 280, which runs north toward San Francisco and south toward San Jose. Public transit is minimal within town limits, but Caltrain stations in Redwood City, Palo Alto, and Menlo Park are all within roughly 17 to 18 minutes by car, making rail access to the broader Bay Area feasible for those willing to drive to the platform.

Cycling in Woodside is a serious pursuit rather than a commuter option. King's Mountain Road draws road cyclists from across the region and has appeared on the Tour of California route, making it one of the more storied climbs on the peninsula. San Francisco International Airport is about 34 minutes away by car, and Mineta San Jose International Airport is roughly 37 minutes in the opposite direction.

Wunderlich County Park is the centerpiece of Woodside's outdoor life, offering open meadows, stables, and trails that wind through groves of towering redwoods, with routes suited to hikers, cyclists, and equestrians alike. The town also maintains its own network trails threading through neighborhoods that welcome all.

Teague Hill Open Space Preserve and Thornewood Open Space Preserve both sit within a few miles of the town center, adding more trail mileage and sweeping views to an already well-forested outdoor inventory. Jasper Ridge Biological Preserve, a Stanford-managed research site about three miles away, offers limited public access and showcases the ecological range of the peninsula's foothills.

Roberts Market on Woodside Road is the town's anchor grocery, with an wide selection, a wine department, and a deli that doubles as a casual community gathering spot. Beyond that single in-town stop, Woodside keeps its commercial footprint deliberately small. Nearby options include Village Square Shopping Center, Woodside Plaza, and Roosevelt Center, all reachable within a 15-minute drive and offering a fuller range of retail.

For major shopping, residents generally head to Redwood City or Palo Alto, where larger retail corridors and more varied stores are close at hand. The trade-off for limited local retail is a preserved, low-traffic streetscape that the town has protected for decades.

Woodside pairs some of the Bay Area's most accessible redwood forests and trails with Michelin-starred dining at The Village Pub, iconic Silicon Valley atmosphere at Buck's of Woodside, and a sweeping network of open space preserves, all while sitting less than 20 minutes from Stanford University and within easy reach of both San Francisco and San Jose.