Windy Hill Open Space Preserve

It’s windy and I like it. The wind washes away the sounds of the trains, the cars, the helicopters and the airplanes of the valley. Be careful on the road up, or if you choose to cross it by bike or on foot. There are plenty of people who race this winding road and create their own velocity related blind spots. Once you’re on the trail, the wind, the views and the ocean air will remind you of why you enjoy the valley on a bad day. On a good day, the wind will give you and extra pat on the back, in case you missed giving one to yourself that day. My friend Eric would take me here for Saturday and Sunday walks. We always had a nice time exploring the trails and gaining elevation.

I started with Lost Trail — Razorback Ridge Trail — Alpine Rd — Hamms Gulch Trail, it is about 8.22 miles for the loop.
Lost Trail is pretty flat
Razorback Ridge Trail, like its name, its twisted, when I was here, there were quit few trail runners, so pay attention while hiking
If you started with Lost Trail to Razorback, you will need to get on Eagle Creek and Alpine Road before getting back to Hamms Gulch.
Hamms Gulch Trail is dog friendly and it is a steady ascending slope (descending if you are coming down from Windy Hill)
Parking is free
All the trails are very well maintained and clearly marked, the view is outstanding.

It’s a gorgeous park that got a lot of hiking trails. It is relatively empty, no so many people. I enjoyed the running here on the edge of deep canyon and creek. But be careful, the bushes here are infested with ticks. And along the trail, a big portion is buried in bushes. I got itchy soon after I finished my running there. After I got home to take shower, a big tick was half body into my skin in my chest, disgusting and unpleasant. Be sure to wear repellent when you go there!

Certainly a gorgeous area, just do not let the picnic tables fool you. There are zero trash cans here.

If you are a hardcore user of the Stanford foothills Dish trail network (and you know who you are), at some point you need to take it up a notch and graduate to Windy Hill. Especially for trail runners who don’t mind getting their gear a bit dirty, Windy Hill presents some delicious possibilities.
From the Portola Valley parking and trailhead, most runners choose a direct route up Spring Ridge to the Skyline Boulevard entrance. Many, however, then turn back around a return the way they came, which misses some of the best parts of the preserve, and ends up being a short route (ca 5.5 miles).
By all means take Spring Ridge up — it’s steep and somewhat grueling, but this access route offers great aerobic exercise. Once at the top, continue deeper into the woods along the Anniversary and Lost Trails. Descend to Alpine Road on the intricately switchbacked Razorback Ridge trail, then take the Eagle Trail to the junction with the Hamms Gulch trail.
At this point, you could either head directly to the trailhead, for a 10 mile loop, or you could head back up to Skyline on Hamms Gulch before heading back down on Spring Ridge. This third option involves a second climb up to the Winy Hill twin summits, and it ups the distance traveled to 15.5 miles. That’s a vigorous route, to be sure, but definitely immerses you in all that this open space has to offer. From open meadows and ocean views to deep gulches, dark forests, and quiet stretches of creekside roads and trails, you’ll discover why Windy Hill is such a beloved place.

First Day at Windy Hill. Unexpectedly so since I was driving back from Fry’s and wasn’t really planning to stop along the way. But I did plan to take some coastal route and did not care which direction I ended up. After a slight mistake going down Alpine road I saw the lower entrance to Windy Hill around the intersection of Willowbrook Drive and Alpine Road. The hiking shoes have been on the feet quite bit for surprise casual hikes. I am happy I had them on once more to allow for a change of pace in the day and so glad I ended up at Windy Hill.
After taking a quick pic of the map in case I needed something to reference I started off. BTW, the entrance was well stocked with maps to take with. I just like leaving the paper for others to use.
For this walk the initial segment was up the lower part of Meadow Trail with a switch over to end up on Sequoias Trails and back down. This can be a little steep for some but no problem for the average person I think with easy rewards of multiple views for Silicon Valley and parts of the bay.
After coming back down I followed the lower trail that mirrors Alpine road for a bit except along a small brook inside the trees. Not much wind at this time so the sounds of the brook flowing over the small rocks along with the birds calling to each other were just heaven. Well most of the time except when a jet flew over. After following the short trail I came to start of Hamm’s Gulch Trail. Who is this «Hamm» anyway? I guess some more research later. The trail itself was indicated to be around 2.6 miles long. Except my goal was to make it all the way up to Skyline Blvd so the other trails made the trip to the top about 3.5 miles. Long the was aromas from at least four different trees that reminded me of hikes around Camp Garland in Oklahoma. lots of birds were out. Squirrels and lizards. While the posting at the part said mountain lions are in the area I did not see any. I did see one bobcat on the way back down who was out at what I thought was an unusual time of the day. Around 6:30 PM on a summer evening. Sundown was much later at 8:10. There were so many places to stop for a great picture I would say to others taking this trail that you will never be disappointed if you forget to take one. Around the next curve will be another stunning sight. A sight that varies from being a clear view to one being framed by the branches and leaves of the trees. There are also a couple of benches along the way to sit and take it all in if you need a rest. The hike down from Skyline to Alpine is much faster but can still take a while to finish because you’ll end up admiring all the things you missed while going up.
Remember to take some water as hike up can take a while. There is water available at both ends but it’s much nicer when you don’t have to worry about. Do like I do and just least a some bottles in the trunk for grab and go.
Transiting Hamm’s Gulch was super fun. I am sure I will be back to Windy Hill again. On the walk back to the car I noticed there are some other trails not on Windy Hill but just as open for hikers. They are located on private land so a little more care must be taken. I’ll try out Old Spanish Trail and Coalmine Ridge Trail next time I am in the area. Consult Google maps as they are shown.
Thanks Windy Hill. It w as great day for an unexpectedly beautiful hike!

Maybe because I’m obsessed with hiking so everytime I discover new hiking place just feel like I find my new treasure and I’m proudly to represent to you who is intersted of following my footsteps…
It was very foggy on Sunday’s morning that made me missed the park I already bookmarked and end up to «Windy Hill Open Space Preserve «. Perfectly fine cause it’s my first time here anyway. The weather wasn’t nice when we (my bestie & I) started the hikes but it didn’t stop us to move on.
There’s a map in the box at the entrance sign but to be honest with you I rarely use it. I’m sure that I will always figure out the way back as long as I remember which trail I take from the beginning.;)
We have 2 options either go left to Windy Hill or right to Hamms Gulch trail. Throw the dice, left or right? Left side seems bright though. Ok, we start on the left. The first 0.5 miles was a little uphill and the path is small so you need to watch out for your steps, get your camera ready for all breathtaking pictures. We didn’t see anyone at that time and thought that maybe not a lots of people coming here or we were too early but later on we saw more and more hikers came from all others direction.
Always nice to have company when you go hiking but don’t be fear if you go alone here, for sure you’ll see more people on the way and that would help your feeling not being so lonely I hope .;)
OMG, beautiful views… I can’t describe all details and it’s better for you to come here that you could see and feel the beauty of nature of your own. The trail is considered easy/​intermediate but it’s a piece of cake for me, hehe !! We started our hike from Skyline parking so mostly downhill first and of course the hardest part (it’s pain on the butt) was on the way back !!
Anyway, we enjoyed it. and saw lots of things from huge dark clouds to beautiful sun shine with clear sky. We saw deers, rabbits, birds, chicks, butterflies and all kind of colorful wild flowers. We met a couple of elders gal friends when we stopped for snapping a pic of the red leaves, they mentioned to us it was poisson oak so we have to be careful. You see beauty is dangerous, lol …
We achieved 8 miles for three hours hike including some breaks for modeling pictures. We didn’t go the whole round of the preserve. I’ll have to save it for the next time cause I know it won’t be my last time here.
Absolutely beautiful and definitely will be back very soon !!!

Original route — start at Portola Rd parking lot. Hike up Hamms Gulch and loop back to Spring Ridge. I missed the turn after finishing Hamms Gulch, hit Skyline Blvd ran back and took advice of ranger to do Razorback, which ended up a better run, mostly shaded less foot traffic. Then ran down Alpine Rd to Eagle trail. I missed the private property sign and ran up that road a good mile or so before realizing that wasn’t Alpine Rd. Turned back around got back and turned back on the trail. Hit up Meadow Trail back on Spring Ridge trail. Thinking this late in the day past 4p that it would beore sun than shade, I opted for the Betty Crowder Trail back to the Portola Rd parking lot. By then I was wiped, feet/​knees are aching. And walked last quarter mile. Still nice turn of surprises. Kicked a rock and tripped over same damn rock along Ridgeback lol. Also tripped over a squirrel. Caught a couple glances of Hawks, and a couple different birds. The original 8e turned into more 10 mile run.

If you park on Skyline, you can do the easy loop around Windy Hill and back but if you want to do a serious walk/​hike, you’ll be going downhill on the way there and uphill on the way back.
So I parked at the Portola Road parking lot to start at the bottom of the hill. The first stretch, before getting tot he Hamm’s Gulch trail, was not very exciting and I was worried. I didn’t feel like I was getting away. Then I turned up Hamm’s Gulch and was transported. Ancient oaks, shimmering prairies, a rocky stream and I felt very far away. After a while, it turns uphill and you’re literally climbing a mountain through a lush and beautiful forest, with a huge diversity of plants. So many different views to enjoy.
Hamm’s Gulch has a lot of switchbacks whereas Spring Ridge is a straight climb. So after emerging from the forest, and walking around Windy Hill, I started my descent down a steep and sometimes slippery gravel path. This part of the hike is exposed with wind blowing over the ridge and making the grass hiss. The forest was covered, without this wind, so this was a nice change. If you walk down Spring Ridge, you are treated to a view of Silicon Valley is second to none. On the right, you can look and see the forest you climbed through. I saw a large group of deer, several bunny rabbits and a lot of lizards.
Near the end, I chose the Betty Crowder trail which is so much nicer than the Ridge Trail that takes you Hamm’s Gulch. Overall, a very pretty, contemplative hike. An online guide said this hike takes 3 – 4 hours. I’m a quick walker and including picture taking and a stop for the restroom, it took me 2.5 hours.
It seemed like more people were doing the hike in reverse of what I did — climbing up Spring Ridge and coming down Hamm’s Gulch — so I might try that next time. There are pit restrooms at the top and the bottom and picnic benches at the main parking lot on Skyline. But there are quite a few benches at the most scenic spots so you could have a rest and a bite to eat and enjoy the view. There’s no water so make sure you bring enough for a long hike.

547 portola rd, portola valley, ca 94 028… use this address for directions to the main entrance and parking lot on portola (overflow parking 0.5 miles away)…come early because the parking lot fills up by late morning… parking available again in the afternoon after the morning crowd leaves… plenty of parking in the overflow lot… windy hill open space preserve provides miles of easy/​intermediate level hiking… gradual inclines and declines… good for trail running… dog friendly, horse friendly, bike friendly and all friendly… mostly open space mix of trails and fire roads… lot of horse manure along the trails… betsy crowder trail provide the best tree coverage and shading, but it’s short… to do a loop, you have to commit to a roughly 8 miles cutting through the center on hamms gulch trail or 15+ miles circling the entire preserve on razorback ridge trail…

Such a great hike! There are two loops to get to the summit — one is about 5 miles and the other 8 miles. The hill lives up to it’s name and is super windy at the top so bring layers. A water bottle is also a must in my opinion. If you take the long route you ascend through the woods and at the summit get sweeping views of the valley including the Stanford campus and San Jose. The way down is on a broader dirt/​gravel path and has some cool prairie type scenery. We went on a weekend but actually didn’t see that many other people on the hike which was nice.

An Excellent steep hike to the Summit. At a steady pace it took me an hour and a half to the summit and a half hour back down. Dogs welcome on leash. Bring water and get an early start. The views are worth every step!

I love this hike. It’s a perfect get back into shape hike. a lot of uphill that doesn’t let up much on the hike from the Portola Valley entry but it’s worth it for the views on the way up and the good calorie burn. We took the 7.4 mile loop. The views are gorgeous and varied vegetation made it even more gorgeous. especially areas of shade and lots of tree understory and ferns… with the noonday sun. We even came across hang gliders taking off. up near the top around skyline! Is it WINDY? It was breezy today. However it was cool and clear and warm head gear advisable as well as lots of removable layers on the body. …And lots of water!!! I will be back here.

With breathtakingly picturesque views, this place is amazing! In fact, we’re making another trip here soon since it has now become one of our favorite hiking spots! We started our hike at around 6:30pm to avoid the heat of the summer afternoon. It was still pretty bright at this time, considering it’s August.
We decided to try the epic and picturesque Spring Ridge Trail, which has a steady and gradual incline, making it a fun moderate hike for us. The views were beautiful and arresting, ranging from areas densely populated with large trees covering some parts of the trail to open spaces of golden rolling hills. We saw quite a variety of flowers along some parts of the trail with vibrant colors. The entire trail somewhat reminded me of some scenes of the shire from The Lord of the Rings movies. Hiking for almost 2 hours, it was a workout we absolutely enjoyed, even though we didn’t reach the peak of the trail.
Other hikers here are generally courteous, greeting you along the trail. It was pretty cool to see several camel back equipped trail runners along the way, profusely sweating as they were making their descent. We didn’t see horse riders or dogs, although it is a trail where they’re allowed. I would consider doing a trail run here sometime soon perhaps.
I would highly recommend this trail for those seeking a moderate hike with uphills and plenty of great views!

This is a NEAR-​PERFECT place not just for hiking, but for TRAIL RUNNING, which is what I will focus on in this review.
Most of the regional parks I’ve visited were never quite the ideal for what I was looking for to do 5 – 10 mile runs. Here are some of my biased/​personal reasons:
1. Most single trails just aren’t that long
2. Shorter trails don’t connect together nicely to form a good, easy to follow route. And most of the ones that do form a loop are still less than 5 miles.
3. Longer trails tend to be paved, which makes it hard on the feet. And in my mind do not classify as «trail runs.»
Windy Hill doesn’t have any of the above issues. I looked at the map, and very quickly planned a rough route that also formed a loop, which is a win because I get to see more nature and don’t have to backtrack!
I ended up starting at the parking lot near Alpine and Portola roads. I came late morning on a Sunday but there was still several spots available, which was great. That tells me it’s not that popular/​mainstream/​accessible to families with little kids. This is in contrast to Rancho near Cupertino, which has way more parking and attracts way more people.
My planned route was to run along the Spring Ridge trail, which cuts across the open space preserve, and connects with the Anniversary Trail at the other side of the preserve, where there is a smaller parking area. That’s about 3 – 3.5 miles. Then I would continue south along the Lost Trail, and Razorback Ridge Trail, and loop back up on the Eagle Trail, back to the main parking lot. In total it’s about 9 miles. A perfect distance and loop for a half marathoner in training.
It. was. brutal. This is why I call it a NEAR perfect place. Spring Ridge Trail is basically continuous incline after incline. I would go up one just to see another waiting. It doesn’t zigzag much either so it feels a lot steeper than it looks. Add that to the fact that there’s very minimal shade. Also add the fact that I was not carrying water on me, and I was running on an empty stomach. I had done several 5 – 8 mile runs on flatter terrain, but apparently 1.5 miles of steady incline and bright shining sun was enough to fatigue me and walk. Like I said. Brutal. BUT, on the positive side, a great workout: P
The good news is once I finally reached the other side of the preserve, at the other parking area, I met a guy coming out of his car and asked if he had extra water. He was holding a water bottle and said, «Yeah! Actually, I have some more in my car.» He brought out a gallon and gave it to me to drink from.
I’m very positive that this man saved my life and enabled me to continue the rest of the run. Thank God for friendly strangers!
More good news. After taking some gulps of the most delicious and refreshing lukewarm water, I started jogging along the Lost Trail. The Lost Trail is awesome, and is where you REALLY feel like you’re trail running. Think narrow dirt paths that carve around hills and take you through the forest. Perfect. And mostly a general decline (with some spots that go up a bit), through a quiet, shaded forest, to my body’s relief. If you do come later in the day when the sun is out, it’s probably best to start here (along Skyline Blvd) rather than the Portola road entrance.
The Lost Trail connects directly to the Razorback Ridge Trail, which is likewise through the forest and general decline. This trail was particularly fun to run because true to its name, the narrow dirt path zigzagged back and forth. This trail takes you all the way back down the ridge, where the Eagle Trail starts. I kept thinking that running UP the Razorback Ridge trail would be pretty painful and not as fun… and I was glad I was going down haha.
The Eagle Trail in comparison to the Lost and Razorback was more plain. Still through forest which is great for the shade, but relatively flat with micro ups and downs. Still more fun than a straight flat paved path though.
I ended up completing the Eagle Trail and ending my run there because I was pretty exhausted. It was the most grueling 8 mile run I’ve ever done because of the inclines that I frontloaded. But boy was it gratifying, thanks to the more exhilarating yet soothing runs that the Lost and Razorback trails provided.
To my dismay, I was still 1.5 miles away from my car. I thought about running. Then I walked. The perfect cooldown.

Very well maintained hiking trails that are well marked. Outhouse toilets at the Portola Road entrance and up at the Skyline Road entrance.
Things that make Windy Hill special:
1– Views of both the bay and the sea from the top of Windy Hill. Most places only have one or the other.
2 — Some nice little creeks running through the forest.
3– Lots of wildflowers (the poppies are exploding right now!)
4 — Bunnies! (I saw at least two.)
5 — Allows dogs on some trails.
I started at the Alpine Road gate and did 8 miles with a friend. We made the mistake, as everyone else has said, of going up Spring Ridge Trail. 1200 feet up with minimal breaks and shade– good thing it’s spring and not summer. Definitely a little sore the next day. However, it was worth it just to turn around and see the awesome view change as we ascended. After that, we went down Hamm’s gulch trail, which was beautifully verdant.
If you’re going to hike from the Alpine Road Entrance and want a 6.8 mile hike:
First: print the map before you go.
Then drive up Alpine Road from 280. The entrance is just past Alpine Rd & Willowbrook Dr (on the Willowbrook side of the road).
Go up Meadow Trail, take a left on what I believe is Eagle Trail toward Hamm’s Gulch. Take Hamm’s Gulch trail up and take a right on Lost Trail, then Anniversary Trail over to Spring Ridge, then back down to Meadow Trail to the entrance.
Bring lots of water if you’re hiking in Summer or the hot parts of Fall. While there are mountain bikers, they seemed very courteous in comparison to folks in other parks I’ve been to.

Great views, dog friendly (on-​leash only I believe) and lots of sunny trails to choose from. Gorgeous views, and a great workout since there were tons of hills to trek on our way to the summit.
— Wildlife: saw a few deer and a lizard, but nothing too crazy.
— Parking: neighborhood parking, pretty easy to find but looks pretty small. We were lucky I guess!
— Bathrooms: didn’t see any, so go beforehand!

Excellent views! The first half of your journey is out in the open (hence the name: «Open Space» Preserve) but after that you’re rewarded with plenty of shade from the trees! I can imagine it getting super hot during the summer so bring sunscreen, a hat and shades. Just came here last weekend and it was niiiiice. Not extremely hot, cold or windy — just perfect! It got a bit chilly at the very top and even a little windy but it was a welcoming feel after sweating up the hills.
It’s really not for the faint-​hearted. The hills aren’t that bad but steep enough to give you a nice derrier challenge! If you like to run trails — the hills will definitely be a great work out.

I love this hike because it’s a short drive from the South Bay and it offers a wide range of elevation and scenery. The seasonal changes are also quite dramatic.
I have chosen a hot and humid day to come here so had prepared at least two large bottles of water for the hike. The 7.2 mile loop starts at the trail head from the Portola Valley parking lot and climbs to the crest of the Santa Cruz Mountains, then descends sharply back through grassland. It’s cool and shaded with trees lining both sides of the trail during the climb-​up and steep dry grassland on the way down.
Start at the trail head and turn left on to Hamms Gulch Trail. Hamms Gulch Trail is very well-​shaded and has foliage of all sorts. I absolutely adore Pacific madrones and got to see quite a few of them on the way up. Afterwards Hamms Gulch then there’s the Lost Trail which cuts through the chaparral, and then ends at a signed junction near the Skyline Boulevard trailhead, at 3.92 miles.
The descend starts from the Anniversary trail, then right on Spring Ridge Trail then take the left on Spring Ridge Trail at the fork. Spring Ridge Trail curves downhill, meeting Betsy Crowder Trail at the edge of a meadow at 6.41 miles. At nearly the bottom turn left on Betsy Crowder Trail then back to the trailhead. This particular hike feel like night and day — mostly shaded on the way up and generally exposed on the way down.
I would say this 7.2 mile loop hike is not too difficult but offers a good workout depending on your chosen pace. There’s 1400 feet in elevation change. One can choose to start from the Portola Valley Trailhead with elevation under 600 feet or the Skyline Boulevard Trailhead with elevation at 1800 feet.

The service here was terrible. Despite it being November, the inconsiderate sun beat down on us while we were making our grueling ascent to the summit, causing us to sweat uncomfortably. Due to the name of the place, we were expecting some wind to cool us off, but the wind was AWOL. Only after we reached the summit did it get windy. Talk about too much too late. Restroom facilities at the summit were notoriously absent, and nobody came and refilled our waters. Needless to say, we didn’t leave a tip.
Other than that, Windy Hill is awesome. This scenic park offers a 1000 foot ascent over a 2-​mile stretch, perfect for getting in shape to do Mission Peak (
) in Fremont.
At the northeast corner of the park is a parking lot that accommodates roughly 40 cars. Additional parking is located outside along the side of Portola Road. There’s also an outhouse at the parking lot, but I didn’t see a drinking fountain anywhere.
The Spring Ridge Trail will take you all the way from Portola Road to the park’s western edge at Skyline Road. This trail is wide and is open to cyclists and horses. Going westward, prepare for a 2-​mile trek uphill with almost no shade. It’s not difficult but does take effort. When you reach Skyline Road, you’ll find a small parking area and the start of the Anniversary Trail (
). At 0.2 miles into the Anniversary Trail is the summit of Windy Hill. Shoot, you could park along Skyline and walk to the summit in 5 minutes. But that just feels like cheating.
At the summit is a small concrete marker (
) and a nice view of other parks (
) and Palo Alto and Stanford (
). Following the Anniversary Trail south will take you to a slightly larger parking area along Skyline. Another outhouse is located here. This is where the Lost Trail begins. This trail is not open to cyclists or horses.
Follow the Lost Trail, turn left onto Hamms Gulch Trail, then left onto the Spring Ridge Trail, and that will take you back to the parking lot on Portola Road. Hamms Gulch Trail is completely shaded, and going eastward it’s all downhill. The total distance covered by the Spring Ridge — Anniversary — Lost — Hamms Gulch loop from the parking lot and back is 7.2 miles. The nice thing about this place is that you take the uphill route to the summit, then for the way back you just let gravity do all the hard work!