Weekly Walker: Take in the Forever Views on Windy Hill

Note: Tom will lead this hike on Saturday, August 10. The group will start from the trailhead on Portola Rd. and hike up Razorback Ridge then down Hamm’s Gulch. This route is 10 miles and will take about 5 hours.

For information, contact Tom at tom@tomdavids.com.

By Tom Davids

Directions: The trailhead is on Skyline Boulevard, two miles south of Highway 84 (La Honda Road).

 Trail Map: www.openspace.org and search for Windy Hill.

Distance: Eight miles.

Time: Four hours.

Special Conditions: For hikers and equestrians only. Dogs not allowed on Lost or Razorback Ridge trails. Chemical toilet and picnic tables at the parking lot/trailhead. No drinking water. This area is often windy, so come prepared. The preserve is managed by Midpeninsula Regional Open Space District.

If you have lived on the Peninsula for any period of time, you’ve seen Windy Hill. It’s the twin grassy hilltops overlooking Portola Valley and is the dominant topographical feature along Skyline Ridge. At the 1,900-foot elevation, the knolls offer unlimited views in all directions, but below the high point there are 1,300 acres of various habitats featuring open grassland, several ridges, and forests of redwood, fir and oak.

This challenging hike takes you from the top of Windy Hill (Skyline Boulevard) to the bottom (Alpine Road) and back again. Along the way, you will enjoy panoramic views of the South Bay. A shady forest of ancient fir trees, seasonal streams and return views of the two summits of Windy Hill.

Begin this hike at the signed trailhead just east of the parking lot, and turn right on Lost Trail. The first quarter mile is over grassland, with uninterrupted panoramic views. “Bob’s Bench”—so identified by a nice bronze plaque squarely placed on the backrest of this sturdy wood bench, is at the trailside and offers an inviting spot for lunch or a rest. It is nearly level, and dogs are allowed until the Hamms Gulch Trail junction, which is only 0.4 mile ahead. 

At this junction are a few of the largest fir trees I’ve seen on the Peninsula. These trees are a reminder of the forest that covered portions of this hillside until logging took over in the mid-1800’s.. Incidentally, this preserve was part of a Mexican land grant belonging to Maximo Martinez, who named the rancho “El Corte de Madera,” meaning “the place where the timber is cut.”

The trailside turns to chaparral as you approach the first junction with Hamms Gulch Trail. Continue on the Lost Trail, but at the junction, notice the very large and very old fir trees. 

Through hillside grass and chaparral, this trail soon crosses a dirt road coming down from Skyline Boulevard, moves through a few switchbacks, and descends to an old ranch road now known as Lost Trail. From that point to Razorback Ridge, the trail is quite level as it moves from ridges to ravines under a thick fir, bay and tanbark oak canopy. 

You will cross several seasonal streams and catch occasional views of the South Bay and beyond.

At the end of Lost Trail, a connecting trail on your right leads to Skyline Boulevard. For this loop, turn left and begin a 1,000-foot descent along Razorback Ridge. Some 20 switchbacks later, you will exit the trail onto a dirt road and then over a bridge to Alpine Road. Turn left on Alpine, and watch for the Eagle Trail beside Corte Madera Creek. Follow this trail for 0.3 mile downstream to a bridge at the gated entrance to private property. Cross over the bridge and turn right onto Hamms Gulch Trail. In a few steps, cross on a wooden bridge over Jones Gulch.

Continue on Hamms Gulch Trail, and begin your climb back to the trailhead. At times the trail is quite steep and muddy when wet, but periodic views to the twin summits of Windy Hill and the grassy hillside of Spring Ridge are your reward.

Continuing uphill, the trail passes to the south side of Hamms Gulch. Huge Douglas fir trees shade the trail as you gain altitude. After a few sharp switchbacks, the trail intersects Lost Trail. Turn right, and a half-mile, you will be back at the trailhead. With a little more effort, climb to the top of the knolls for true 360-degree views.

By the Way…

Another interesting and much shorter trail off Skyline Blvd. is the Anniversary Trail, built to celebrate the 10th anniversary of Windy  Hill’s purchase. This trail is less than a mile. It is quite level and features two benches located in the saddle between the two knobs offering a great spot for rest and reflection and forever views.