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    Windy Hill Open Space Preserve

    4.6 (169 reviews)
    Closed 7:00 am - 7:00 pm
    Updated over 3 months ago

    Windy Hill Open Space Preserve Photos

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    Joyce T.

    Fun and easy trail, not steep inclines and lot of tree shades. We hiked via Hamms Gulch trail and go all the way up to 3 miles trail and decided to turned back the same way. It will take total 5 miles to reach the top. The weather was too hot 80+ at 4pm ish.

    Bike parking
    Brandon L.

    Very pretty! I was passing down Portola Rd and stopped here to use the bike parking and public restroom off of the parking lot. I saw a bunch of people getting ready to hike with their dogs. The parking lot is gravel, but there are plenty of spaces. The restroom is clean-ish, it's an enclosed building but there's no running water - they have toilets that are more like porter potty style (dumps into holes in the ground) and hand sanitizer instead of a sink. But for convenience this was great.

    Gabrielle B.

    This is a loop that you can do clockwise or counterclockwise. It's pretty intuitive but it's not well marked for this specific loop and you end up on a lot of different trail names so make sure you look at your map so you don't get lost. I wasn't super impressed with the views- pretty barren and the hills are so small. The woodsy area is nice though. When I did the hike I saw several rattlesnakes in the sunny sections which was terrifying! Be careful.

    Seen from anniversary trail
    Rebecca C.

    Amazing place to hike with flat grounds and overall beautiful views of the bay. Also it's not crowded. If you want less exposure and less wind, head south toward Lost Trail (longer trail, 2 hours long). If it's not too windy, head left toward Anniversary Trail (can be done as loop, less than an hour)

    Katie R.

    As with most of the preserves on the Mid Pen Open Space Preserve list, this place has views for days! Spectacular take your breath away views...and it's not just because you hiked over 3 miles up hill to see them! There's a bottom parking lot accessible through Portola Valley and one up top that's accessible from Skyline Rd. If you're in the mood to see some good views and don't want to do a hard hike to find them, enter through skyline! From here you can do a little exploring without having to get a full hike in. If you do want to get the whole hike in, start from the bottom that way you start with the uphill battle and end with the down hill. We hiked Windy Hill Loop clockwise from the bottom parking lot on a beautiful *clear and not too hot* day. According to All Trails this loop is about 6.2 miles, if you read into it and look at the starting point on their map it seems that is is actually closer to 7. Unfortunately my friend was unable to find parking so I hopped in her car and parked about 3/4 miles down the road. What was supposed to be a just over 6 mile hike turned into what was closer to an 8 mile hike for us. In doing the trail clockwise from the bottom, the first half was lovely! This part of the trail took you through trees, over a creek, and on a lot of switch backs to get you up there. There were still some fairly steep climbs here and there, but the majority of the trail was shaded switch backs. The views on this side were nice, but only once you got closer to the top did they start to really get amazing. Going down the trail on the other side was a different story, it was steep and sunny. So steep that it really wasn't fun and ended up being kind of painful on my knees (I hav bad knees) and quads. The views on this side however were great. No trees to block out the view...but also no trees to block out the sun. I probably won't do this loop trail again because I didn't find the 2nd half enjoyable. I would love to come back and do a smaller portion of the trail from the top (and not end up down hill) just to see those views again.

    Markus N.

    Two months ago on a trip to Hayes Valley for dumpling treats on a weekday I parked on a slight incline near the dumpling establishment. Not like a Pac Heights hill or the Castro, a gentle slope. Upon parking I busied myself stashing or packing every single item even remotely visible as you all know what happens if you don't do that in this shining example of an amazing American city. Then off to the delicious dumplings we went. Returned within the two hours to find a gift from SF's finest under my wiper blade. 59 clams for not curbing my wheels. I've lived in SF and parked in SF for three decades and have gotten a variety of tickets for a variety of reasons but never one for this. The steep hills have signs instructing the wheel curbing behavior. The gentle ones do not. The ticket referenced the SF muni code as its justification. What complete jerks. Upon exiting our maiden voyage to Windy Hill yesterday we returned to the vehicle parked carefully off the driving surface on the proper side of the white line in an area where there are no signs saying don't do this and so many folks did because the Windy Hill parking lot is pretty small and as we neared the windshield wiper there was a little white paper flapping and my smile turned upside down and the sheriff was two cars ahead leaving more flapping papers and I grabbed it and looked then looked again and ... it was a $0 warning. I looked again. A message saying don't do this again here's how to do it properly. Take note, SF, of a much better way to get your message across. If you were perfect, SF, maybe you'd have a reason to be mean, but you aren't. We thanked the officer as we drove away, still amazed. With respect to Windy Hill itself, pretty perfect conserved space, excellent loop trail up to Skyline w awesome views, birds and flowers. In the summer you'll want to ascend via the southern trail (Hamm's Gulch) and descend on the one to the north (Spring Hill) as the latter has no shade while the former is shaded and cool and much better for the up part of the adventure. There are also a few small lots on Skyline and you could park and go down then up but who really wants to finish a walk with the up part. Thank you again, officer, for your kindness. We will definitely situate our ride properly next time. And thank you Windy Hill for a perfect 9-mile ish workout in a beautiful setting on a beautiful day.

    If you like hiking and watching sunrise this is the place. One of the Best place to hike, watch sunrise and watch the cloud drift!

    Sunil R.

    I had an amazing hike here earlier this week! It was an overcast day and when we made it to the top, the cloud layer was below us and we saw the sunrise over the East Bay Hills. Memorable moment! My friend said that on a clear day, you can see SF as well. I plan to come back for that. Note that getting directions to the park from Apple Maps takes you to a neighborhood. Look for Windy Hill Preserve parking lot on Google and that will take you to the right spot.

    Vivi B.

    We did it! 10 miles! Spring Ridge Trail to Anniversary Trail to Lost Trail to Razorback Ridge Trail to Hamms Gulch Trail. Took about 4 hours and we stopped twice. Spring Ridge is slow, steady, climb up. Very wide but a bit crowded with lots of dogs on leashes. Very hot. Top of Anniversary Trail there were two people getting ready to paraglide off the mountain. Gorgeous 360 degree views and you can see San Francisco in the distance. Lost trail was very muddy since it had rained the day before - I loved it. Felt like a kid again stomping in the mud. Razorback Ridge Trail is a very slow decline with lots of switchbacks. It did get cold since the sun was setting. Parking is a little tough (Saturday at noon) but I only had to wait 5 minutes for someone to come and leave.

    Ketryk W.

    Beautiful rolling hills on the top of the Santa Cruz mountains to catch the sunset or overlook the Bay from the other side.

    Ee Vonn Y.

    Great on-leash dog trail. I walked the entire trail that was dog-accessible, and recorded 8.4 miles in 3.5 hours. I'm a slow hiker, and my dog needed plenty of breaks. Even at 9AM, there was available parking across the street on Portola Trail. My path: Betsy Crowder Trail (very cool and shaded) Sequoias Trail Hamms Gulch Trail (shaded and lots of uphill) Lost Trail (no shade, hotter, flowers!) Anniversary Trail (surprisingly muddy for the altitude) Windy Hill Summit (hardest part bc of the mud) Spring Ridge Trail (hotter, no shade, but all downhill and small rocky terrain) Betsy Crowder Trail (back to the shade) There is internet access for almost the entire trail so it's easier to find your way if you feel you wandered off the wrong path for 2 miles. Compared to Mission Peak, there's more to see, and the difficulty level is the same because it's moderately difficult, and the time to complete is longer. I definitely will be back because there's more to see here, but my dog probably won't want to come back.

    Windy Hill Open Space Preserve Map
    Joyce H.

    There is so many great places to hike in the Bay and like most of the Preserves in the area you won't be disappointed. This 1,335-acre preserve is filled with grassland ridges and forests covered with redwoods, fir and oaks. The hikes at Windy Hill are indeed on the breezy side but it's a great place in the summer when you need a little cooling off from the warm sun. One of my favorite hikes is taking Lost Trail to the end and back making a nice 5 mile hike. Doggies are allowed, on leash, on most trails except Lost and Razorback Trail.

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    A real beauty of a hike that is great for inexperienced hikers are those with "not the best" cardio lol. Always worth it

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    Page 1 of 5

    Ask the Community - Windy Hill Open Space Preserve

    Review Highlights - Windy Hill Open Space Preserve

    I went clockwise (up Spring Ridge and down Hamms Gulch) - steep initially but the hike got easier as I went along.

    Mentioned in 17 reviews

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    Wunderlich Park

    Wunderlich Park

    4.2
    (131 reviews)
    5.2 km

    Small Wunder A…read more940-acre park nestled in the eastern Redwoods and madrone-laden slopes of King Mountain. The name of the park is derived from contractor Martin Wunderlich, who donated the land to San Mateo County. The Good: * Free to visit * Parking lot * Picnic tables available * Restroom in parking lot * Seventeen miles of trails, including several loops. * If you like horses, then this is the place for you! There's a really cool old historic stable and lots of equine action to be found. * Camping available (https://www.smcgov.org/parks/make-reservation) The Meh: * Currently, no recreational horse activities like trail rides and lessons are available. * Crazy elevation gains, as trail elevations run from ±350' to over 4,300'. Be sure to check the trail guides to make sure you don't get in over your head. * No dogs allowed The Ugly: * The restroom has no running water, just hand sanitizer. * I'll admit, I'm not a fan of horses, and having to share trails with horses isn't my idea of a good time. Conclusion: Not the biggest park in this area that's full of fantastic OSPs, but it's certainly worth a visit--especially if you're a hippophile.

    Hiked at Wunderlich Park on a sunny Saturday in March! We used AllTrails for directions and we…read morereached around 9am - to our surprise, the parking lot was full by then so definitely recommend coming earlier. There were multiple cars circling around looking for a spot as well. We ended up waiting about 30 minutes before parking. We did the Bear Gulch and Alambique trail clockwise. There are some brief steep sections, but for the most part, the trail was moderate in terms of difficulty. We didn't encounter too many people despite all the cars in the lot. We spotted a small snake on the trail and there was a lot of horse manure on the Alambique portions, so we had to watch our step closely. The trail was mostly shaded which was nice, but there wasn't much of a view. Overall, the trail was well marked and maintained (minus the manure on Alambique). Good hike for a sunny day, but the parking lot situation could be improved.

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    Horse stables
    Horse stables
    Wunderlich Park
    Wunderlich Park

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    Pearson Arastradero Preserve

    Pearson Arastradero Preserve

    4.0
    (117 reviews)
    3.2 km

    An underrated gem hiding in plain sight Pearson-Arastradero…read morePreserve genuinely surprised me. The Arastradero Creek + Acorn Loop (~2.5 miles) packs in way more variety than you'd expect from a short trail -- you start in cool, shaded creek corridor that feels completely removed from the suburbs, then the path opens up into sweeping golden grasslands with those big, open Bay Area skies that make you remember why you live here. The difficulty sits right at that sweet spot between "actually a walk in the park" and "satisfying enough to feel like a real hike." Elevation gain is gentle but present, terrain is well-maintained dirt trail, and the whole loop flows naturally without any confusing junctions. Wildlife spotting is a real highlight -- keep your eyes up and you'll likely catch red-tailed hawks riding thermals over the hills. Early morning is magical here. So is sunset. A few practical notes: parking is free, dogs are welcome on leash, and the trailhead is easy to find off Arastradero Road. It never felt overcrowded on my visit, which for the Bay Area is honestly remarkable. If you're in Palo Alto or anywhere on the Peninsula and need a quick mental reset without a long drive, this is the move. One of those places you'll want to keep to yourself -- but can't help telling people about.

    Decided to go running here this past weekend and was glad there was no winding road on the drive…read moreover. Appreciated the conveniences I found, including a strong cell phone signal in the area, a parking lot on site, and restrooms at the gateway building just steps away. There was a bit of seating and several nature exhibits educating visitors about the surrounding habitats. Interactive displays included bird calls of the quail, red-shouldered hawk, and meadowlark, and animal tracks of creatures like raccoons, bobcats, deer, and coyotes imprinted with descriptions. Deer, coyote, and rabbit scat too, though I found the accuracy of this display questionable. The only actual poop I saw on the trail was horse manure... piles of it. The place had multiple trails with easy access from the parking lot. I mainly hiked the Redtail Loop which stretched through the grassy hills, with scenic views and a few benches along the way, and of course plenty of clear signs noting the connecting trails and miles on each marker as well as the path to Arastradero Lake. The gateway facility and trails appeared to be well kept, a great setting altogether for getting your steps in or just taking in the fresh air and tranquil environment.

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    Gateway building/trails
    Gateway building/trails
    Pup by the lake
    Pup by the lake
    Pearson Arastradero Preserve

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    Coal Mine Ridge Nature Preserve

    Coal Mine Ridge Nature Preserve

    4.5
    (15 reviews)
    2.6 km

    Well maintained hiking spot! We chose this hike because…read moreafter we were headed to Alpine Inn for dinner. We found the last parking spot along the road and headed up to the start of the hike. There are maps available or you can take a picture of the posted map. After hiking a short way we found a door to the entrance to the coal mine trail. Once at the top we found amazing views of Bay Area. We found an amazing tree to eat a snack under. There was a beautiful rose on the tree so this must we a known place to have a romantic picnic at. The weather was perfect so not a problem with the trails. There was a well maintained bridge as well. It was a moderate hike.

    I've only been here twice, and only when my daughter attends the birthday party of a classmate who…read morelives in Portola Valley. Maybe I'm not paying attention on other trails, but this is a great place to find interesting mushrooms to photograph. There's shade, nice views of the valley, a few short bridges, and lots of interesting vegetation, from the ferns to the fungi. In the winter it's wet and lush. The trail is quite narrow in places, and it was slightly muddy due to the recent rains, but I was able to avoid getting too dirty. There's a network of trails that's accessible from this trailhead. I don't really have a destination in mind when I come here - usually I just hike for about an hour and turn back. There were a good number of cars parked near the trailhead, but I didn't run into that many people on the trail itself.

    Photos
    Rose
    Rose
    Views on way to top
    Views on way to top
    Tree with Rose

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    Tree with Rose

    Windy Hill Open Space Preserve - parks - Updated August 2026

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