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.