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Plan Your Own
The trailhead on Portola Valley Road is adjacent to the Sequoias residence community. Look out for the brown WINDY HILL sign around the bend in the road. It is not very obvious so keep a look out so you don’t miss it. When you pull in the dirt road off of Portola Valley Road, you will find a large parking lot that has room for horse trailers and usually has some spots left to park even on busy times during the weekend. There is also a large bathroom just in case. The trailhead starts near the bathroom.
Dirt parking lot Trailhead and bathroom
This review covers the Betsy Crowder and Windy Hill Summit trails. Roundtrip from the trailhead off of Portola Valley Road uphill to the summit on Skyline Blvd (18660 Skyline Boulevard, Portola Valley, CA 94028) and back is 6.8 miles. Betsy Crowder trail is relatively narrow 1.3 miles and is open to pedestrians only. Windy Hill Summit trail is open to bicycles, pedestrians and equestrians.
From the trailhead, walk about one quarter of a mile, then you have the option to bear left (multipurpose trail) or straight/right onto the Betsy Crowder trail (look for the gate).
Betsy Crowder trail gate Shady part of trail
The trail takes you past a brown water pond on your left and is shady for the first half of the trail. Then the trail opens up to a field and sunshine. The Betsy Crowder trail intersects with the Windy Hill Summit trail (fire road) just past another gate. This trail is all uphill so you can go as far as you want. All the way to the summit is another 2.1 miles or turnaround whenever you feel like it.
Brown pond Green grassy field
Gate near the intersection with Windy Hill Summit trail
There is some shade initially and then the trail becomes fully exposed to the sun.
Shady area Exit to the sun
There are views along the way because it is a nice climb up the hill.
Views from the trail
Uphill dirt trail
More views from the trail