Windy Hill Open Space Preserve — Attraction in Portola Valley

I love this place, mostly because I didn’t get bit by a rattlesnake. It’s easy to enjoy a place if you just judge it by wether you get bit by a rattlesnake. I’m starting to appreciate the DMV so much more, I haven’t seen a snake there once. I can’t say the same about Windy Hill. I didn’t see this rattlesnake until I was about to step on it. Luckily I was able to avoid it just in time. After that experience I was just happy to not be going to the hospital. The one critique I have for this place is their signs. They had a sign that explained what to do if attacked by a mountain lion. It said “if attacked, fight back”. To me that seemed a bit self explanatory. That would be like if a pool had a sign that said, “if drowning, start swimming”. That wasn’t even the worst part about the sign. It also had a picture of what parents should do if they encounter a mountain lion with their kids. Parents are suppose to pick them up and hold them in front of them, kind of like a cute little shield. It’s almost like the sign wants parents to sacrifice their kids to the mountain lion. Another sign I didn’t agree with was the “Not Potable” sign. The sign was placed right next to a tub of water. I’d imagine this sign would be extremely frustrating for those that brought pots on their hike and don’t have the best vocabulary. They might want to put that water in their pots, I mean it’s already in a tub, why on Earth can’t it go in a pot. I don’t have the best vocabulary and typically I would be confused by a word like “potable”, but for some reason I remember that day in school where they talked about “potable”. I know it means “drinkable”, but why couldn’t they just say that. Don’t speak in code! Besides the signs, this hike...

Windy Hill is one of my favorite places to hike in South Bay. I just went last week and hiked the summit with a friend. Parking is easy and totally free - we parked in the lot about two miles from Skyline, and if you don't get a spot you can park on the street. The trailhead has a basic portapitty. It takes about an hour and a half or so and has a couple of steep sections, but is definitely moderate. I wish I had brought some water. When you hit the parking lot on Shoreline, keep going! It's worth the last small pitch to see the beautiful views from the "summit" of both sides of the Bay. At the top, there was a kid flying a kite and a couple picnicking while watching sunset. Beware that the sunset is brilliant ;) so you might need sunglasses. My friend and I watched sunset then walked back down in the dark, which is totally doable as long as you have a flashlight and enough clothes on that you're not too cold. Because the path is wide and well maintained, Windy Hill seems like a great trail for runners and dog walkers. I hope you enjoy this beautiful spot! I'm definitely going back with my boyfriend for wine and...

My sister, boyfriend and I hiked the dirt trail 3.7 miles from the Portola Road parking lot up to the Windy Hill Summit! It was long, but worth it (7.4m round trip). We loved the sun, cool breeze, and panoramic views of the bay area leading up to the peak. I'd rate this hike difficulty as medium.

The trails are dog and horse friendly and we encountered many cute puppies and some horse poop but no horses. Many people do not clean the poop off the trails so remember to look down when you are hiking to avoid a stinky situation. It was hot and we enjoyed the shade and trees at the beginning of the trail. There is a steeper stretch in the middle of the trail with no shade but it passes quickly. Don't forget to bring water, especially if its a hot day.

Unfortunately, halfway on the trail my sister had to run back to the trailhead and parking lot to use the bathroom. She ended up getting an extra workout and running back to meet us (there is cell service on most of this trail so we could call and text each other). Her bathroom experience included sharing the toilet with flies but there was toilet paper and...