The hook
Two bald grassy summits on the Skyline ridge with a full-circle view: bay and valley on one side, ridges rolling to the ocean on the other.
01Why it's worth it
Most of the Skyline ridge is wooded, but Windy Hill breaks into open grassland at the top, two bare knobs that hand you one of the best all-around views on the peninsula. The whole valley and bay lie to the east, ridges fold away toward the ocean to the west, and on breezy afternoons hang gliders launch off the slope, which is how it got the name. You can drive to the top and walk five minutes to the view, or earn it with a genuine climb from the valley floor. The grass is gold in summer and green in winter, and the wind really is part of the deal.
02How to experience it
For the easy version, park at the Skyline (Highway 35) lot and take the short path to the summits. For the workout, climb from the Portola Valley side. Come on a clear day for the view, a windy afternoon for the gliders. Cyclists know it well from the Skyline ride.