Trip Report: Windy Hill Open Space Preserve

March 28, 2021

windy hill open space preserve

On a cool but crystal clear Sunday afternoon in March, I set off to complete a hike that had been on my radar for quite awhile.  With views promising to impress, spanning nearly the entire Bay Area, I was excited to get to the summit of Windy Hill at Windy Hill Open Space Preserve!

Miles/Elevation:

6.2 miles

1,400 feet

About Windy Hill Open Space Preserve:

windy hill open space preserve

Windy Hill Open Space Preserve is a part of the Midpeninsula Regional Open Space District, and contains a combination of hiking and mountain biking trails.  Aptly named for the prominent Windy Hill, this preserve has been around since 1980, and features 1,335 acres of open hill tops and dense forests of Redwoods and oaks.

The highlight of this preserve is Windy Hill, the summit of which can be seen from much of the surrounding area.  This prominent, grassy peak, can be accessed either via two hiking trails that ascend the eastern face of the Santa Cruz Mountains, or via Skyline Drive.

While this preserve isn’t gigantic, the views definitely pack a punch.  Windy Hill Preserve may have the best views of any of the spots I have been to in the Bay Area, and that’s saying something considering the quality of hiking in the Bay!

Hiking in the Santa Cruz Mountains? Be sure to check out Castle Rock State Park!

Getting To Windy Hill Open Space Preserve:

Windy Hill Open Space Preserve lies on the Peninsula in the San Francisco Bay Area.  The easiest way to access the park is via I-280 which runs between San Jose and San Francisco.  The lower trailheads are a few miles off the interstate, and are easily reached along nicely paved roads.

To reach the upper side of Windy Hill, visitors can also approach the preserve via Skyline Drive.  Skyline Drive (highway 35) straddles a ridge of the Santa Cruz Mountains, and essentially forms the western border of the preserve.  If your goal is to get great views without the work of hiking up to the ridge, this is the best way to get there.

To the lower trailheads, it is about a 25 minute drive from San Jose and a 30 minute drive from SFO.

To the upper parking lots with easy access to the summit and the accompanying views, it is a 35 minute drive from both San Jose and SFO.

Windy Hill Loop:

The Ascent

Starting at the Alpine Trail Trailhead at the base of the preserve, the Windy Hill Loop hike begins with a choice: you can either hike in a clockwise direction or a counterclockwise direction.  It may not seem like a big deal, but there is definitely a right answer to this question.

I highly recommend hiking in a clockwise direction.  First, if you do it in this direction, most of your climbing will be along shaded trails, and if you are here in a warmer month, it can get quite hot.  Second, by hiking clockwise you will hike down the Spring Ridge Trail, which has awesome views throughout.  If you hiked up this trail, you would be staring uphill the whole time.  By hiking down this section, you will have expansive views essentially the entire time.  

windy hill open space preserve

So, starting in a clockwise direction, the trail starts by crossing a bridge, and quickly takes a couple of left turns in the first quarter mile.  I definitely recommend having Alltrails or something similar open on your phone because there are a couple of intersections that aren’t super well marked.

windy hill open space preserve

Eventually, you will wind up on the Hamms Gulch Trail which will lead you to the top of the ridge.  This trail climbs consistently, but if you are in decent shape it’s never overly steep.  The trail primarily travels through forest, and you will see some beautiful old oak trees as you hike.  There are some occasional panoramic views, and a couple nice places to stop, but it’s mostly a hike through the woods.

windy hill open space preserve

Emerging at the top of the ridge with the loudening sounds of Skyline Drive nearby, the foliage thins as you leave the forest and begin hiking through the ridgetop meadows.  At this point, the views really open up and you begin to see the wide open panoramas this place is famous for.  Keep going, because they get better at the top!

windy hill open space preserve

Shortly after leaving the forest, you will pass one of the parking lots on Skyline Drive, and from here it is about a half mile of gentle climbing to the summit of Windy Hill.  After a short climb, you will be at the summit!  Don’t expect to have it to yourself because this is a popular place because it’s so easy to get here from Skyline Drive, but you’ll be paying more attention to the views than the people!

Always be sure to follow the 7 Leave No Trace Principles when in the outdoors!

Images From The Summit:

windy hill open space preserve

Looking towards San Francisco and Stanford

The Descent:

After thoroughly exploring the summit area and taking in all aspects of the 360 degree views, it’s time to start your descent.  While you could descend via the same trail you got here on, you definitely should complete the loop and hike down the Spring Ridge Trail.

From the summit, you can actually see most of the Spring Ridge Trail; it descends the hillside right below you!  This trail is pretty steep in places, and it is totally exposed; you will not have shade the vast majority of the time.  Fortunately, the things that would make it brutal to ascend make the views on the descent stellar throughout!

It’s steep but the views are great!

The descent might be tough on your knees, and it is also used as a mountain bike trail so you do need to be aware of that, but overall it’s a pretty nice descent.  Eventually, you will reenter the forest, and you will have a couple of turns to make to find your way back to the trailhead.  Fortunately, most of the preserve has decent cell service, so your phone should work to have your map and directions up!

Topdown Lifestyle Rating: 8/10

I’m tempted to give this hike a 9/10 because the views are fantastic, and the trail is really nice, but I have one problem with this hike: you can drive to the top. Maybe it’s unfair to punish a hike because there’s a road to the top, but it just doesn’t seem necessary to do the hike when you can just drive there. Windy Hill is awesome, and you should definitely go up there, but I’d probably drive to Windy Hill and then do another hike!

windy hill open space preserve
Back in the trees, almost to the trailhead!

Pros:

  • Some of the Bay Area’s best views
  • Pleasant ascent and beautiful descent
  • Quiet compared to some Bay Area hikes (but you won’t be alone)
  • Very nice, well graded, trail

Cons:

  • Tons of people near the summit
  • No real point to hiking all the up to Windy Hill when you can drive there

Alternative Hikes:

North Ridge Trail Purisima Creek Redwoods

 Hamms Gulch, Eagle Trail, and Lost Trail Loop

 Razorback Ridge Trail to Lost Trail – California

When To Visit Windy Hill Open Space Preserve:

Windy Hill Open Space Preserve is a 4 season destination.  In summer, you can expect to sweat on exposed sections of trails, and to be comfortable on the shaded sections.  During winter, expect to be cool in the shaded areas, and still warm in exposed sections.  Rain is most likely in winter and spring. If you want the hills to be green instead of brown plan to visit in late winter or spring!

Always follow basic trail etiquette when on trail!

Links for Further Reading:

Windy Hill Preserve | Midpeninsula Regional Open Space District

Best trails in Windy Hill Open Space, California

Hike Spring Ridge Trail Windy Hill Open Space Preserve – POST

Windy Hill Open Space Preserve

More about Nathan Foust

My name is Nathan Foust, and I am a teacher from 9 to 5, and an adventurer on my off days. I’m originally from La Crosse Wisconsin, and I currently live in San Jose California. I love my job, and besides work, I enjoy hiking, travel, coaching basketball, watching sports, drinking beer, and arguing about anything and everything.

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