Climb up, walk down
Windy Hill Open Space Preserve

Neil Wiley

If you are like me, you would rather do your most strenuous, uphill climbing in the morning, then amble downhill in the afternoon. Although most hikes along Skyline take you downhill first, Windy Hill is an exception. If you enter the preserve from the Portola Valley entrance, you can climb Hamms Gulch Trail or Razorback Ridge Trail up to Skyline, then return on the other trail, or opt for the one-mile shorter but steeper Spring Ridge Trail to go back down. Spring Ridge Trail offers great views of the San Francisco Bay and peninsula, but it is in the open without shade. Whatever loop you choose, you’ll hike from seven to eight miles with an elevation gain of about 1400 feet.

If you have less time or don’t like long uphills, but want to see a great view, enter the preserve from the Skyline entrance, then take the Anniversary Trail for a short walk up to Windy Hill. It takes only a few minutes but rewards you with an exceptional 360-degree view—a nice rest stop on a Skyline Boulevard drive.

Both entrances provide off-road parking in a large, gravel lot, a restroom, and a signboard with maps. There are no entry or parking fees, but there is no running water either. As a pleasant bonus, the Skyline entrance also offers three picnic tables, usually in shade, in a small grassy meadow.


Windy Hill Open Space Preserve features 13 miles of trail serving 1,312 acres of open grassland ridges, forests of redwood, fir, and oak, a small accessible creek, and a small inaccessible pond. Although most trails are open to hikers and equestrians, Hamms Gulch, Lost, and Razorback trails may be closed during the wet season. The preserve is dog-friendly, and most trails are open to leashed dogs. The exceptions are Razorback Ridge Trail, Eagle Trail, and sections of Lost Trail. (MNN columnist M. Cecilia Saleme recommended this preserve in her July column.) Bicyclists are limited to Spring Ridge Trail, Meadow Trail, and Sequoias Trail.

My hike

I parked my car in the Portola parking lot, picked up a map at the trailhead, and chose the newer narrow-track, shady Betsy Crowder Trail around the pond and to Meadow Trail, then up Hamms Gulch Trail. (Note: This lower section of the preserve has several intersecting trails, and although signage is good, it is best to refer to your map at each intersection.)

Although Hamms Gulch Trail is uphill, most of the grades are easy and shaded. The first part of the trail runs along a pleasant little creek. The few steep sections use switchbacks to ease the climb. And even the upper sections are cooled by relatively heavy forest and large ferns. Nevertheless, I was glad when I reached the ridge.

I turned right on Lost Trail, and walked on the flat to the Skyline trailhead, where I enjoyed lunch at a shaded picnic table. While there, I talked with a Wall Streeter from New York, a man happy with his recent retirement to California, and with Tina, a mosquito abatement officer with San Mateo County, who was happy to be doing worthwhile work. I agreed with both of them.

I took a short nap on the tabletop, but when a turkey vulture circled overhead, I decided it was time to move.

I walked north on Anniversary Trail to Windy Hill. An unmarked trail behind a bench took me to the top to see the view. (You can take a second short detour up another hill, too.) I continued on Anniversary Trail, then down the steep and wide Spring Ridge Trail to Betsy Crowder Trail and the Portola entrance. Total distance: about eight miles.

I especially enjoyed this loop because an old friend and mentor, Carl Larson, was one of the donors who created the Windy Hill Loop. He was a favorite client and a good friend. Now I owe him even more.


To reach the Portola entrance, take Highway 280 to Alpine Road. Turn left on Alpine about 2.9 miles to Portola Road. Turn right on Portola Road and travel 0.8 miles to the parking lot and entrance. Watch for a small sign. It is easy to miss.

To reach the Skyline entrance, take Skyline Boulevard (Highway 35) to 4.9 miles north of Page Mill Road.


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