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Anniversary Trail Loop, Windy Hill Open Space





by Transit & Trails


Wildlife Sightings

by iNaturalist


Length: 1.3 miles
Difficulty: Easy
Duration: Halfday
Created by Bay Nature

Good for:
  • Dogs
  • Views
  • Grasslands
  • Trail Hiking


Not surprisingly, spectacular views and stiff breezes are hallmarks of Windy Hill Open Space Preserve, which mounts the east-facing slope of the ridge above Portola Valley. The remarkable 360-degree vista at the top of the ridge, from ocean to bay, is ample reward for ascending Anniversary Trail. Hikers, bicyclists, and equestrians enjoy 12 miles of trails that traverse oak, madrone, buckeye, bay, fir, and redwood and then open up to grassy slopes.

The bent dry grasses along the crests point eastward, evidence of the prevailing wind spilling off the Pacific. The extensive open grassland here is one of few such expanses on the ridge of the Santa Cruz Mountains that forms the spine of the Peninsula. In Peninsula Tales and Trails, David Weintraub writes, "The shape of the terrain, combined with periodic fires and grazing, have kept the upper hillsides here mostly free of trees and shrubs since Spanish missionaries passed by in 1769."

There are six park entrances from the eastern boundaries at Portola Road and Alpine Road, all leading to a 1,000-foot elevation gain approaching Skyline Boulevard at the western boundary, where there are four entrances. Windy Hill is ideal for kite flying and hang gliding (permit info at <a class="external-link" href="http://openspace.org">openspace.org</a>).

Getting there: For lower entrances, take Interstate 280 to Alpine Road in Portola Valley and head south three miles, then right on Portola Road, and .8 miles to a lot on the left. For upper entrances, take Skyline (Highway 35) 2.3 miles south from Highway 84 or five miles north from Page Mill.

Hike by Rob Lehman, originally published in the October 2010 issue of Bay Nature magazine


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