Get to Know Woodside

Scenic Woodside is true to its name. Trees have been a constant in this town high in the hills of San Mateo County, though the current redwoods represent a third generation of growth. That’s because Woodside supplied the lumber to build San Francisco twice: before the Gold Rush (its first sawmill was running by 1838) and then after the 1906 Earthquake. It also attracted the time’s high society types, many of whom were taken by Woodside’s natural beauty and commissioned country mansions from the city’s preeminent architects. Filoli, designed by Willis Polk, is an enduring example that’s now open for all to visit. Woodside’s modest business district has a distinct Old West character, consisting primarily of historic civic buildings, the c.1880 Pioneer Saloon, a few small shops, and two well-regarded restaurants. The ever-eclectic Buck’s has gained fame as a legendary breakfast rendezvous for Silicon Valley tech founders meeting their VC suitors.

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Living on the San Francisco Peninsula

Except for its northern tip, which is occupied by the city itself, the San Francisco Peninsula lies almost entirely within San Mateo County — the second-most populous in the Bay Area, after San Francisco County. By sharing the only land border with San Francisco, the towns and villages of the Peninsula form a literal and figurative mainline to the city. Beginning with the railroad’s arrival in the 1860s, the towns along the Bayshore side of the Peninsula developed into San Francisco’s first commuter suburbs, and they’ve only grown since. They’re separated from the coast by the rugged, redwood-flanked slopes of the Coast Range, which effectively split the Peninsula — and county — into two distinct moods. The towns along Highway 1 move to a slower beat, from rustic Pescadero to the gnarly breaks of Half Moon Bay, home to the world-famous Mavericks big wave surfing competition.