Windy Hill South Loop

MODERATE 2 reviews
#5 of 6 trails in

Windy Hill South Loop is a 8.3 mile moderately trafficked loop trail located near Portola Valley, California that features beautiful wild flowers. The trail is rated as moderate and primarily used for hiking, walking, and trail running. Dogs are also able to use this trail but must be kept on leash.

8.3 miles 1843 feet Loop

dogs on leash


trail running




wild flowers

A nice quick escape for Peninsula hikers in need of a fix and a good workout. This is a good hike to knock out if you're short on time, live in the area and don't want to waste time driving. You still get great scenery, a bit of wildlife, moody weather, and more and yet you can launch just outside of Portola Valley. But on the flip-side you'll see a lot of people and hear some road noise once you near Skyline.

1 month ago

Good for trail running, not so much for hiking, few Vista points and cold in the winter.

2 years ago

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 hand sanitizer.