Choose Your Own Adventure at Windy Hill

Lost Trail at Windy Hill

Overview: 5-mile hike, mostly flat and almost completely shaded on the crest of the Santa Cruz Mountains

Distance: 5 miles out and back if you do the full trail, shown on the Google Map below. See hike description for details on shorter options.

Elevation change: 1,900 feet of low-intensity elevation change as you contour the ridgeline

Difficulty: Moderate

Hiking time: 3.5 hours

Season: All year

Getting there: Head south on Skyline Blvd (Highway 35) from Highway 84. Turn left into the Anniversary Trail parking lot.

Parking lot address: Anniversary Trail, Portola Valley, CA 94028

Managing agency: Midpeninsula Regional Open Space District

Trail map: View online

Hike Description

When I’m looking for a pleasant walk in nature or I’m with a group of folks with different abilities, this hike is one of my favorites: Lost Trail traverses the top of Windy Hill Open Space Preserve, but it’s not too strenuous. Plus, the area provides options for shortening your outing to better fit the preferences of your group.

(Now if I want a cardio and endurance workout, I hike up from the bottom of Hamm’s Gulch at Windy Hill, but that’s a different story.)

Here’s what I recommend: Pile in the car and head west on Highway 84. Take a left on Skyline Boulevard (Highway 35) heading south and park at the Anniversary Trail and Picnic Tables parking lot at the top of Windy Hill. From Woodside, this is only about a 15-minute drive. There you’ll find ample parking, picnic tables and a restroom (the other parking areas don’t have restrooms).

There is great signage at this trailhead, so take a peek at the map and then stop to appreciate the amazing views west to the Pacific, and east over the entirety of the San Francisco Bay. On a clear day, you can take in Mount Hamilton in the South Bay, Mount Diablo in the East Bay and Mount Tamalpias to the north of the Golden Gate Bridge.

Choose your own adventure

Here’s where you have some options: There are benches and picnic tables around this area for those looking to relax. A short walk north on the Anniversary Trail takes you to the Herb Grench Overlook. Or, head south to hike the Lost Trail.

Dog owners: Please note that after about a half mile, you’ll reach a point where Lost Trail intersects with the Hamms Gulch Trail. Sorry, dogs have to end their trek on Lost Trail here—but there are several other dog-friendly options at Windy Hill, if that’s what you’re looking for.

With my groups, it’s worked well to have some people head back to Anniversary Trail to take it easy and enjoy the views, while the rest of the group continues on Lost Trail for about 2 miles to hook up to the southernmost parking lot for Windy Hill. Then, the group that hung back around the Anniversary Trail can drive on Skyline to pick up the hiking group from this lot. Win-win!

Hiking the Lost Trail

Lost Trail roughly follows Skyline Boulevard south, but it has gentle, mostly single-track footing. While there are some short ups and downs, kids and others will enjoy the fabulous views, without a lot of physical effort. At many points, you’re still deep in the trees, so you get that feeling of being really immersed in nature.

Likewise, if the weather is damp (as it can often be at the top of Windy Hill), most of the trail hugs the hill through the trees, so you stay relatively protected.

Around the 2-mile-mark, you’ll see a sign for the Razorback Ridge Trail. Make sure to take the trail to your right, which hooks up with a parking lot off of Skyline, about 2.5 miles from where you started. (If you take Razorback Trail to the left, you’ll be in for another workout!)

Here’s where you could be picked up by car, or, simply turn around and hike back, for a nice, even 5-mile out-and-back trip.

It’s just right

No matter what you choose at Windy Hill, you’re in for a ton of nature, fresh air and great views! Plus, after you’ve worked up a thirst or perhaps a hankering for a burger, you can always stop at the famed Alice’s Restaurant at the junction of Highways 84 and 35 on your way home. What could be better?