That is the kind of place where the Bay Area's tech wealth seems very far away, even though Woodside and Portola Valley, home to some of the most expensive real estate in the country, are only a few kilometres down the hill.
The roads are the reason riders come. Skyline Boulevard, State Route 35, runs along the crest of the Santa Cruz Mountains, with redwoods and Douglas firs on both sides, and the cross roads, such as Highway 84, plunge down to the coast through shaded canyons. The corners are tight and technical, the surface is variable, patched and sometimes lined with fallen needles, and the light comes through the trees in broken shafts, so judging the road takes concentration. On a weekend you will meet plenty of other riders and cyclists.
Alice's Restaurant, a rustic roadside spot at the crossing of Skyline and Highway 84, has been a biker meeting place for decades and is worth a stop, if only to look at the bikes lined up outside and swap notes. It is a casual place with simple American food and good conversation.
The redwoods here are second growth, since the original giants were cut in the nineteenth century to build San Francisco, but they have recovered into dense, dark groves where fog drips off the needles. Some old stumps are huge. The smell of damp bark and bay laurel is strong.
For fuel, ride down into Woodside or on to Redwood City or Half Moon Bay, because the ridge itself has little. The best weather is spring and autumn, with summer fog often creeping over the crest and chilling things. Watch for deer at dusk and gravel in the tight bends after rain.