Near Lost Trail
The Anniversary Trail makes its way up Windy Hill.
Near Lost Trail
Views of the Stanford Dish, Hoover Tower, and the surrounding Stanford campus from a small rock outcrop just off the trail. Even though it's obstructed, it's a nice view.
Near Lost Trail
The temperature and climate change the higher you climb. The shade provides relief from the sun, no matter what time of day.
Near Lost Trail
Flowers bloom in the tall grass as the trail makes its way to the Anniversary Trail.
Near Lost Trail
The Anniversary Trail as it makes its way up Windy Hill.

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Hike Trail

Lost Trail

3.3 (4 Ratings)
A beautiful trail that follows along Skyline Boulevard.
3
mi
Distance
268
ft
Gain
easy
Difficulty
ViewsWildflowers
Access Issues
The Windy Hill Open Space Preserve is open 30 minutes before sunrise to 30 minutes after sunset throughout the year. Dogs are not allowed on a majority of the trail, although they area allowed between the Hamms Gulch Trail intersection and the end of the Lost Trail.

Route Details

Flatter
Steeper
2.96mi
Distance
268ft
Elevation Gain
494ft
Elevation Loss
45%
Max Grade
2,022ft
High Point
1,639ft
Low Point
Path Type
Point to Point
Description
The Lost Trail provides access to the Anniversary Trail and the summit of Windy Hill. It also connects the Razorback Ridge, Hamms Gulch, and Spring Ridge Trail in the Windy Hill Open Preserve, creating a great loop for those wanting a longer outing without having to retrace your steps. The trail begins along Skyline Boulevard and descends into the the preserve. You are always close to the road, so you'll hear cars and motorcycles as they travel along Skyline Boulevard. After roughly .4 of a mile, the Razorback Ridge Trail breaks off to the right and descends to Alpine Road in Portola Valley. Continuing straight, the trail rises and falls as it works along the hill top. Views are obscured mostly by trees in the area. Ferns and flowering plants can be seen along the trail, especially in the spring. A little after the 2 mile mark, the Hamms Gulch Trail breaks off to the right and descends through Windy Hill Preserve, offering a few views of Windy Hill and other parts of the preserve. The Lost Trail continues straight ahead and meanders along the hill top. Views of Windy Hill start to come into view as you approach the Anniversary Trail, which leads to the Windy Hill summit. The trail ends at a parking lot on Skyline Boulevard. At this point, you can turn around and return to where you started, or follow the Anniversary Trail to the summit of Windy Hill, where great views of the Bay area spread out before you.

Route Conditions

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Anonymous Adventurer
All Clear
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All Clear
Anonymous Adventurer
Some Issues
Anonymous Adventurer
Some Issues
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Contributors
David Hitchcock