Windy Hill Open Space Preserve Portola valley, CA

The perfect name.

If someone asked you, "where are you going?" You can just say, "Windy Hill", which is exactly what this is. It's a big open space that makes its way up to a hill where you can catch amazing views of the bay. We visited in late February and boy, was it chilly (and windy)!

There are lots of trails here to make it a short or long hike, and several different trail heads. We started from the Portola Road parking lot and decided to do a 7.3 mile loop (although Google clocked it in at 8.27 miles). We started counter-clockwise to hit the switchbacks and steepest part of the incline, first.

Make sure you start early! We arrived at 9 am and the parking lot was already more than half full! By the time we left (1 pm-ish) it was so busy cars were parked along the street as over flow.

Portola Road trail head

Spring Ridge > Hamms Gulch > Lost Trail > Anniversary Trail > Spring Ridge > Betsy Crowder

When you start from the Portola Road trail head you'll follow a wide, hard packed trail. Bear left at the first fork and follow signs for Spring Ridge trail. You'll see some buildings/offices on your left. It's pretty unimpressive, but hang in there.

Keep following the trail...or the crowds. This was the only other group we saw who let their dogs off leash - and we came across a lot of crowds.

The faster one.

Always a few minutes behind...I'm turning into an old man!

At the next trail sign, you want to make sure to follow Hamms Gulch Trail.

This is where things start to get interesting...

We can't resist windy dirt paths!

The trail starts to wind its way down to a creek.


Before slowly making its way uphill. You'll hit another trail gate. Keep following the signs for Hamms Gulch.

This is where the trail starts to get really good. Oh, and harder.

This is also the most covered part of the trail.

I may be getting slower, but the humans are still the slowest.

Clouds kept coming and going but we don't mind the overcast. It felt like we were in a Jane Austen novel. Very English country side feel.


Steady incline and lots of switchbacks. Hamms Gulch was our favorite part of the hike, especially after a wet winter. It's very green, lush, and the perfect temperature. It's also one of the quieter parts. We still ran into other folks and doggies (all leashed), but it wasn't too frequently.

When the sun peaked through the clouds we got the most amazing light.

As you get higher don't forget to look around and behind you every now and then. The view starts to peek through the trees.

I'm a pretty big guy, but not this big! The switchbacks can get pretty steep.

Technically, you're going to follow Lost Trail to start making your way back, but just follow signs to Windy Hill Summit.

We lost cell reception along this part but it's ok because there are so many clear trail signs.

You'll know when you reach the end of Hamms Gulch. The trees start to thin out, the brush gets drier, the wind stronger and all you start to see is open sky.

This part of the trail also gives you some options for a snack/lunch break. We chose to stop at Bob's Bench, since it's always nice eating with a view. Although, it was quite chilly so we had to eat fast. Well, at least the humans had to eat fast. I always eat fast.

There are also picnic tables and a toilet at the Anniversary trail head, which is only a short walk to the Windy Hill summit. This is also another option: to park and start at the top along Skyline Boulevard.

Keep walking past the Anniversary trailhead/parking lot and at your first fork, bear right to stay on Anniversary trail. You may see signs marked 'Trail' but those are for horse back riders.

This part of the route is basically your way back and is all downhill. Additionally, it's also all exposed from here on.

These views! If you look closely, you can see the trail that leads you all the way back.

The nice thing about the exposed part of the trail is that it gives you a chance to warm up, although, I bet in the summer this can be pretty brutal.

After about 0.6 miles from the Anniversary trail parking you'll arrive at another parking lot, on your left and a trail head on your right. This is the Spring Ridge parking area, along Skyline Blvd. Bear right and follow signs that either mention Spring Ridge trail or Portola Rd parking.

If you're not sure, chances are you'll have cell reception again, so it's easy to look it up on your map.

The whole way down is a mix of hard packed dirt and gravel, which can get very slippery, especially when walking with your pup, on leash.

Water break! Well, at least for the pups...

This is also the busiest part of the trail. There was always either a group in front of us, or behind us. Very dog friendly, as well, although all on leash.

Since there's a clear view all the way down, Mom would alternate between on leash and off. Since my recall is pretty good it's easy, but if you're not sure, then you definitely want to keep your pup leashed.

The other reason Mom risks getting a ticket is because it's actually so slippery here, since it's so dry, that it's safer to walk with me off leash, but I'm a pretty big guy. If you have a smaller pup I don't think it would make that much of a difference.

Once it leveled out, back on leash I go!

On the way down, on Spring Ridge trail, you're going to come across 2 forks: at the first one, bear left to stay on Spring Ridge; at the second one, bear left to follow Betsy Crowder trail.

At the end of Betsy Crowder trail you're going to cross a trail gate and you'll come across the next sign at a fork. You want to bear left/straight and follow Spring Ridge Trail, again. This takes you directly back to the parking lot.

This is probably one of the most varied trails we've tried - and definitely worth it! Perhaps it's quieter on non-holiday weekends. Also, make sure to check for ticks. This is another one where Mom just pulls them off me as we go, and then pulls off a handful more once we get home.

Your fur parents want to know:

  • Yes, there is parking
  • No, this is not an off leash park/trail
  • No, this is not a fenced enclosure
  • No, there are no doggy (or human) water fountains
  • No, there are no poop bags
  • No, there are no trash bins (not even at trail head)
  • Yes, there are benches (at Windy Hill summit)
  • Yes, there are toilets (at Portola Rd trail head and Anniversary trail head)

🐾 Caesar

Report Abuse

If you feel that this video content violates the Adobe Terms of Use, you may report this content by filling out this quick form.

To report a Copyright Violation, please follow Section 17 in the Terms of Use.