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Anniversary Trail



0.6 mile 1.0 kilometer point to point
91% Runnable


Ascent: 102' 31 m
Descent: -95' -29 m
High: 1,890' 576 m
Low: 1,788' 545 m


Avg Grade: 6% (3°)
Max Grade: 15% (8°)


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Trail shared by David Hitchcock

A trail with beautiful views to the Windy Hill Summit.

David Hitchcock

Features Views · Wildflowers · Wildlife

The Windy Hill Open Space Preserve is open 30 minutes before sunrise to 30 minutes after sunset throughout the year.

Runner Notes

The trail is relatively free from obstacles, making it a nice run along the hillsides.


The Anniversary Trail can accessed by heading up the Spring Ridge Trail or the Hamms Gulch Trail from Portola Valley. It can also be accessed by taking Skyline Boulevard to the Windy Hill Open Space Preserve and parking in one of the parking lots there.

The trail departs the parking lot and works its way through open fields that provide fantastic views of the San Francisco Bay area. On windy days, the grasses move like waves around the hills. Wildflowers bloom in the spring along the trail. Shortly after departing the parking lot, an equestrian trail goes off to the left and follows the road while the Anniversary Trail turns to the right and begins to gently climb the hillside toward the summit of Windy Hill. There is a bench on the right hand side of the trail where you can take in the views.

The trail is a narrow, singletrack dirt path as it wraps around one of the hills. The view expands as more of the Bay Area comes into view. You can see the Spring Ridge Trail climbing from Portola Valley through the Windy Hill Open Preserve. At roughly .4 miles, the Herb Gulch Trail goes off to the left and climbs to the summit of a nearby hill. Traveling roughly another .1 miles, the trail to the Windy Hill summit goes off to the left. The trail climbs up and around the hill until it reaches the summit, where there is a marker. Take a minute to enjoy the view.

Returning to the main trail, follow it to the left as it descends quickly toward the Spring Ridge Trail. The trail passes through a couple of shrub lined areas before emerging at another parking lot on Skyline Boulevard. At the parking lot, there is an information kiosk with information regarding things going on in the Windy Hill Open Space Preserve. From here, the Spring Ridge Trail descends into Portola Valley via a steep descent. If you parked at the other parking lot on Skyline, you can return via the path that you traveled or take the equestrian trail that follows the road.

Flora & Fauna

Flowers bloom along the trail in the spring time. Deer, rabbits, and coyotes have been seen along the trail. Mountain lions have been seen, so be on the lookout in the evenings and early mornings.

Turkey vultures and hawks can often be seen riding the air currents above the trail.


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  4.5 from 2 votes
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53 Views Last Month
2,367 Since May 1, 2016



The Anniversary Trail makes its way up Windy Hill.
Apr 27, 2016 near Portola…, CA
Views the surrounding hills spread out before you. Fog can roll over the hills in the evening causing it to be much cooler than where you started.
Apr 27, 2016 near Portola…, CA
Views of a couple resting on a bench on one of the hills at the top of the preserve.
Apr 27, 2016 near Portola…, CA
Stanford Dish area and the San Francisco Bay beyond on a hazy day from the summit of Windy Hill.
Apr 27, 2016 near Portola…, CA
Skyline Boulevard runs just outside the preserve. If you don't want to climb to the top, you can drive to the parking lots on either side of the hill.
Apr 27, 2016 near Portola…, CA
Windy Hill marker at the summit.
Apr 27, 2016 near Portola…, CA