Hiking the Ridge Trail with Friends at Windy Hill

The Bay Area Ridge Trail at the Windy Hill Open Space Preserve is an easy hike through the woods in the Santa Cruz Mountains above the Portola Valley. The trail breaks into open grassland shortly before reaching the 1,900-foot summit and its sweeping view of San Francisco Bay. Bring your friends.

We are hiking the nearly 400-mile Bay Area Ridge Trail. Sign up to follow our progress here.

TRAIL MAP (date hiked)

Dan’s Journal

Windy Hill is what happens when you flip through your Ridge Trail book looking for a segment to hike and press the “easy button.”

Most of the 3.2-mile trail is shaded. The elevation gain is minimal. The peak may be the easiest bag in the Santa Cruz Mountains. And lunch is waiting for you a mile or two up Skyline Boulevard at Alice’s Restaurant in Woodside. What could be better? Invite some friends to join you! It all made for a pretty perfect morning.

Looking for something a bit more challenging at Windy Hill? Begin deep in the Portola Valley and hike the Spring Hill Trail to the summit. Return to the valley via the gnarled and twisted woods that line the Hamms Gulch Trail. We enjoyed that challenge back in the spring. (Find our post from that hike here.) But on this summer day, it was all about easy.

San Francisco Bay and the Santa Cruz Mountains from the Windy Hill summit. Dan Page/CoastsideSlacking

Miles we hiked


(with returns and connectors)

Elevation gain






Our Progress Hiking the Bay Area Ridge Trail – 124 out of 394 miles


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