Windy Hill Hike Overview

Distance: 1.5 mile loop

Elevation change: 100 feet

Difficulty: Easy

Hiking time: 1 hour

Season: This hike is accessible and enjoyable all year.

Getting there: The parking lot closest to the trailhead is located off of Skyline Boulevard (Highway 35), 2.3 miles south of Highway 84 (La Honda Road) and 4.9 miles north of Page Mill Road.

Parking lot address: Click here

Windy Hill Hike
The gradual climb on the ridge at Windy Hill. Photo: Teddy Miller
Bay Area View
Views of the Bay and foothills near the summit of POST-protected Windy Hill. Photo: Teddy Miller

Hike Description:
Did you know that Windy Hill was the first open space protected by POST? It’s a favorite among many POST staff and supporters, as well as others throughout the Bay Area!

This short hike to the summit of Windy Hill provides a 360-degree panorama, including views of the Pacific Ocean and of the Bay.

To complete this trail as a loop, start at the Anniversary Trail parking lot off Skyline Boulevard and follow the trail to the left up the hill. For the next half mile, the trail climbs gradually through grassy ridges to the summit of Windy Hill.

From the top of the hill, you will have views spanning the Bay to the ocean. To the left of the trail is a short path to a viewing area with benches. I recommend taking this detour to take in the sights near the summit. On a clear day, you can see all the way to San Francisco, Mt. Diablo and potentially even Mt. Tamalpais!

After taking a few minutes to enjoy the view at the summit, retrace your steps back to the Anniversary Trail and continue along the top of the ridge as the trail starts to slope down towards the trailhead for the Spring Ridge Trail. Once you pass the junction for the Anniversary and Spring Ridge trail, turn left to loop back to the start. The trail parallels Skyline Boulevard to return you to the parking lot.


The 1,335-acre Windy Hill Open Space Preserve features open grassland ridges and forests of redwood, fir and oak. This preserve is now managed by our partners at the Midpeninsula Regional Open Space District

About Post

Peninsula Open Space Trust (POST) protects open space on the Peninsula and in the South Bay for the benefit of all. Since its founding in 1977, POST has been responsible for saving more than 87,000 acres as permanently protected land in San Mateo, Santa Clara and Santa Cruz counties. Learn more

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