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A trail with good views of the bay area through the woods from Portola Valley to Skyline Boulevard.

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1,800' 549 m


660' 201 m


1,146' 349 m


46' 14 m



Avg Grade (5°)


Max Grade (11°)

Dogs Leashed

Features Views · Wildflowers

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 fairly smooth, making for easy running. There are several sections where there are more roots in the trail or part of the trail has been impacted by erosion. However, it's fairly easy running, especially if you are coming downhill.


The Hamms Gulch Trail starts in Portola Valley and climbs to Skyline Boulevard, where you can access the summit of Windy Hill and take in breathtaking views of the Bay Area. While the distance is greater than that of the Spring Ridge Trail, the climb is more enjoyable because it is not as steep and a majority of the trail is shaded by the trees of the surrounding forests. Access to the trail is via the Spring Ridge Trail and Meadow Trail from the parking area in Portola Valley, although you can access it via the Lost Trail from one of the parking lots along Skyline Boulevard.

After running along the Spring Ridge Trail and part of the Meadow Trail, which goes off the right at a junction, the Hamms Gulch Trail descends along a creek until you leave the preserve temporarily. The trail winds down to a small creek, which can be crossed easily by rock hop, even in the winter or early spring when there may be more water in the creek. The Eagle Trail goes off to the left from here via another creek crossing and provides access to the Razorback Ridge Trail.

The Hamms Gulch Trail continues to the right and re-enters the preserve through a small gate as your climb toward Skyline Boulevard. While not as steep of a climb as the Spring Ridge Trail, you'll be ascending for the next 2 miles. The trail follows Hamms Gulch, which sits on the right had side of the trail. Ferns sit along the left hand side of the trail while mosses cover the trees at this point. The right hand side of the trail drops into the gulch.

After climbing switchbacks at roughly 1 mile, the trail level outs along a ridge line for roughly .2 miles, proving a slight break to all the climbing. The trail climbs via a set of switchbacks at this point, where views of Windy Hill are off to the right. A bench provides the opportunity to take a break, enjoy the view, and grab a snack. As you climb, the forest takes on the characteristics of an evergreen forest. The air is cooler at the top of the trail, so make sure to have a long sleeve shirt, especially if you are on trail in the morning or later in the afternoon.

At roughly 2.5 miles, there is a small side trail that leads to a rock outcrop where views of the Bay Area spread out before you. Continuing on for another .2 miles, the trail meets up with the Lost Trail. From here, you can turn around and return to your car, or follow the Lost Trail to either the Spring Ridge Trail (shortest) or Razorback Ridge Trail if you want to run more.

Flora & Fauna

Deer, rabbits, turkeys, and various types of birds can be seen, especially in the mornings or in the events. A majority of the trail is in the woods, so various types of ferns, mosses, and flowers can be seen, especially in the spring. Because of the change in elevation, you can experience different types of forests as you climb toward the end of the trail.


Shared By:

David Hitchcock

Trail Ratings

  4.0 from 4 votes


  4.0 from 4 votes
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Trail Rankings


in California


7 Views Last Month
1,315 Since Jun 20, 2016
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The Hamms Gulch Trail re-enters the preserve as it begins climbing away from the creek.
Apr 27, 2016 near Portola…, CA
Views of the Stanford Dish, Hoover Tower, and the surrounding Stanford campus from a small rock outcrop just off the trail. Even though it's obstructed, it's a nice view.
Apr 27, 2016 near Portola…, CA
Views of Windy Hill come into view as you climb the hill.
Apr 27, 2016 near Portola…, CA
Views of the bay area and hills through the trees.
Apr 27, 2016 near Portola…, CA
Views of the surrounding hills.
Apr 24, 2016 near Portola…, CA
The trail is level through this section before it starts climbing deeper into the woods.
Apr 27, 2016 near Portola…, CA



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Sep 2, 2018
Paul Cothenet

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