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Windy Hill Open Space Preserve

November 11th, 2020

6.2 miles
1400 vertical feet
Total Time: 1:53

Starting elevation
548 feet
Max elevation
1910 feet

Rating: 6/10

Directions: Take Interstate 280 to Alpine Road west. Turn right on Portola Road. Turn left into the parking lot (there's a sign on your right).   View Driving Map



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GPX File

(Note: GPS didn't start until over a mile in.)

I hadn't done a Bay Area day hike since last year, partly because I knew all the trails were seeing heavy traffic in the age of Covid-19. So I'm not sure why I thought today, Veteran's Day, would be any different.

Oblivious, I drove over to Wunderlich County Park only to find the small parking lot full and cars circling, waiting for spots. It was 10am. I didn't know if I'd have to wait 10 minutes or an hour, so I decided I'd pivot to someplace reasonably close, Windy Hill.

I figured that even if the lot at Windy Hill was full, I could park on the side of the road (something not allowed at Wunderlich), or at the Portola Valley Town Center down the road. As it turned out, I got one of the last open parking spots - and the best one, right next to the trailhead.

It's a mild climb at the start before turning uphill to the right at an intersection. I shortly passed the other end of the Betsy Crowder Trail (on the right) and continued climbing. It's mostly unshaded, with brief sections under trees. After one such section, I emerged to see my first view of Windy Hill looming up next to Skyline Boulevard.

View of Windy Hill (top left)

Dogs and bicycles are allowed on the trail, so expect to see both. They didn't seem too numerous, though. It's about 2.5 miles from the trailhead up to the top, with the views getting better as you climb higher. The Spring Ridge Trail tops out at the parking lot on Skyline. Just before reaching the parking lot, I took the Anniversary Trail to the left. From there I went past a bench (the top of Windy Hill is to the right from here) and continued to another bench where I turned right to visit the Herb Grench Overlook (there's another bench here). There are nice views of the bay from here. There are also nice views across Skyline toward the ocean.

Looking down from the Anniversary Trail

Anniversary Trail

Another view from the Anniversary Trail

Looking across Skyline Boulevard from near the Herb Grench Overlook

After taking some pictures, I backtracked to the first bench and went up to the top of Windy Hill, then started the return descent on the same trails I'd taken up.

View of the Bay

Looking down across the preserve

Another view of the Bay

Skyline from near the top of Windy Hill

View from the top of Windy Hill

One of the few forested sections


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