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Fighting The Winds At Windy Hill Open Space Preserve

Updated: Jan 26, 2022

Location : Portola Valley, CA

Parking : Free parking along neighborhood streets

Trail type : Out and Back

Trail Length : 6.5 miles

Elevation Gain : 1374 ft

Difficulty : Moderate

Trails traversed : Hamm Gulch Trail > Lost Trail > Anniversary Trail

Post-hike pit stop suggestion : Alpine Inn on Alpine Road, Portola Valley


This is an excellent hike and a great workout with plenty of variety of rolling hills, mountains and wooded area. This OSP offers a number of trails but the Windy Hill Loop is by far the most popular. As the name suggests, it gets quite windy at the summit, so dress in layers.


Parking for this trail is available along Alpine Road and the neighborhood streets close to the trail. At the park gate, follow the Hamm Gulch Trail. This trail, although narrow, is shaded most of the way, but quite steep in some areas. The trail climbs uphill throughout, until it intersects with Lost Trail. Make a right on the Lost Trail. At this point, you are out of the wooded area, and the climb becomes more gradual.

Green turns into Golden Brown on Lost Trail

The green shrubbery gives way to California brown as you near the second entrance of the park, off Highway 35 (Skyline Blvd). Take a quick break at the restrooms available at the entrance, before you make your way on Anniversary Trail.

At the entrance on Skyline Blvd

Anniversary Trail is almost flat and takes you, first, to a smaller unnamed hilltop, before winding up Windy Hill.

Anniversary Trail is flat and offers a good respite from all the climbing.

At 1919ft, Windy Hill provides a birds eye view of the entire Peninsula, and like the name suggests, is quite windy at the top. With a bench or two available to rest your tired feet, this is a great spot for a short snack break before heading back along the same route you just came up on.

For a lunch break, or just to wet your whistle, the historic Alpine Inn is close by and offers an expansive outdoor seating while dishing out some great comfort food.

Lunch at Alpine Inn


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