Windy Hill Loop

Windy Hill Open Space Preserve has one of my favorite loops. Beginning in Portola Valley and rising to Skyline Blvd, the route has a great mix of singletrack, forest, meadows, streams, and views.

The run begins at the main parking area for Windy Hill. I usually take the fireroad on the way in and the Betsy Crowder Trail on the way back. The narrower Hamms Gulch Trail is reached after 0.8 miles and it descends into the forest and Corte Madera Creek which is flowing nicely after the recent rains. The stream flowing out of Hamms Gulch is crossed and this can be a tricky rock-hop in late winter, but dry for now. A small uphill brings you to the junction where the Hamms Gulch Trail continues up the hill. I usually hit the Hamms Gulch Trail on the downhill (Razorback Ridge is such a perfectly graded ascent trail) so I head down to the Eagle Trail towards Razorback Ridge.

The Eagle Trail is a fun 0.6 mile stretch of single track next to gorgeous Corte Madera Creek, which has many cascades, smooth river rocks, and lush forest. Next, there is a short steep hill on pavement and then the Razorback Ridge Trail appears on the left. This lovely trail switchbacks 1,200 vertical feet up the ridge in 2.3 miles. At 4.3 miles after beginning, the Lost Trail (Bay Area Ridge Trail) is reached which is another highlight. This trail trends slightly downhill 1.2 miles as it contours the slope in douglas fir (some huge firs here) and maple forest, and then enters an open area and uphill for the last 0.5 miles to the Hamms Gulch Trail junction.

At this point, you can either take Hamms Gulch Trail down or add a 2 mile extension by continuing to the summit of Windy Hill and doing the Anniversary Trail Loop. The Anniversary Trail is well worth the extra time if you have it with spectacular views of the Silicon Valley on one side and the Santa Cruz Mountains on the other. Once back at the Hamms Gulch Trail the descent is still enjoyable despite the newly constructed water troughs that are like speed bumps. On the way back I complete the run by taking the Meadow Trail to the Betsy Crowder Trail which is a nice final stretch of running in hardwood forest.

Route (12 miles including Anniversary Loop, 10 miles without): Map of Preserve

  • Start at main parking area
  • Fireroad toward Alpine Road
  • Straight at junction with Spring Ridge Trail
  • Hamms Gulch Trail
  • Eagle Trail
  • Razorback Ridge Trail
  • Lost Trail
  • Anniversary Trail Loop (2 mile addition)
  • Hamms Gulch Trail
  • Meadow Trail
  • Spring Ridge Trail
  • Betsy Crowder Trail

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