4.7
(27)
1,982
runners
113
runs
Jogging in Windy Hill Open Space Preserve offers access to over 12 miles of trails across a 1,300-acre preserve. The terrain climbs from Portola Valley to Skyline Ridge, featuring a distinct wind-swept hilltop that reaches just under 1,900 feet. The preserve is characterized by diverse landscapes, including redwood, fir, and oak forests, as well as expansive open grassland ridges. These varied ecosystems provide a range of running environments, from shaded woodlands to exposed hilltops with wide views.
Last updated: June 26, 2026
4.5
(2)
67
runners
16.7km
02:13
490m
490m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
runners
11.8km
01:32
290m
290m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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6
runners
29.0km
03:47
790m
790m
Hard run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.
35
runners
10.2km
01:15
200m
200m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
11
runners
7.65km
01:00
200m
200m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Windy Hill Open Space Preserve
The hike from Razorback Ridge trailhead to the Windyhill summit is mostly through shaded sections. Sections of it kept cool from the fog rolling in from the Santa Cruz Mountains. The final section, Anniversary Trail is out in the open but has nice views of the bay.
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Along the Old Spanish Trail, thereโs a small bench tucked under eucalyptus trees where you get a clear view of Mt. Diablo. Itโs a good spot to pause, catch your breath, and take in the landscape.
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On a clear day, you can see up the bay to San Francisco and out across Silicon Valley. The trail follows a packed dirt track which winds above the treetops, granting sweeping views from this northern section.
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Borel Hill is my favorite place to watch spring flowers. The western slope near ancient oaks (5-10min west of Borel Hill) are covered with orange California Poppies and purple flowers starting in April. Borel Hill itself peaks around mid May and has a wide variety of flowers. The show lasts only a few weeks until end of May. The peak time and flower intensity varies from year to year, so come several times between April and May. There is small summit NW of Borel Hill and a narrow dirt trail leads you to a rock within 2 min. The rock is big enough for 2-3 to sit on. On a sunny day, the rock is nice warm even if the air is cold. Good views on the ocean and the Bay.
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Windy Hill Summit, located at an elevation of 1,905 feet within the Windy Hill Open Space Preserve, offers great views of Silicon Valley and the Peninsula. The preserve stretches 1,132 acres along the east side of the Santa Cruz Mountains, coming up from the valley road near Portola Valley to this scenic summit. Itโs a great spot to watch the sunset and take in views.
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The top of Borel Hill has an elevation of 2,572 feet and offers panoramic views of the city below as well as views of the ocean in the distance.
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Windy Hill Open Space Preserve encompasses a little over 1,100 acres of barren land with a few spotty forest areas. The majority of the Peninsula Range (the mountain range in which the park is encompassed) is completely covered in trees, but the Windy Hill Open Space Preserve has a bunch of open meadows and bald hills with expansive views.
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Windy Hill Open Space Preserve offers a wide selection of running routes. You'll find over 90 different jogging trails to explore, catering to various preferences and fitness levels.
The preserve features diverse terrain, ranging from shaded redwood, fir, and oak forests to expansive open grassland ridges. You'll encounter trails with significant elevation gains, especially towards the wind-swept hilltop, and some sections can be muddy after winter storms. Trails vary from mostly paved surfaces to tricky, steep terrains with roots and rocks.
Yes, Windy Hill Open Space Preserve has several excellent loop options for runners. A popular choice is the Running loop from Portola Valley, which is a moderate 5.1-mile path. For a longer challenge, consider the Alpine Pond โ Borel Hill loop from Portola Valley, an 18.0-mile trail.
Yes, the preserve offers routes suitable for all skill levels. While many trails involve elevation, there are easier sections and moderate paths available. Out of over 90 routes, about 15 are rated as easy, and 66 as moderate, providing plenty of options for less strenuous runs.
For experienced runners seeking a challenge, Windy Hill Open Space Preserve has several difficult routes. The Windy Hill Summit loop from Portola Valley is a demanding 14.5-mile trail with significant elevation gain, offering panoramic views. There are 17 routes rated as difficult in the preserve.
Joggers are rewarded with spectacular panoramic views, especially from higher elevations and the summit. You can enjoy sweeping vistas of the San Francisco Bay, Stanford University, and the Pacific Ocean. The Windy Hill Open Space Preserve Scenic View is a particularly notable viewpoint.
Absolutely. While running, you can pass through Portola Valley, reach the prominent Windy Hill Summit, and traverse the scenic Spring Ridge Trail. The preserve itself, with its diverse ecosystems and wind-swept hilltop, is a natural landmark.
Yes, dogs are permitted on the trails at Windy Hill Open Space Preserve. It's a great place to enjoy a run with your canine companion, but always remember to follow preserve rules regarding leashes and waste.
The preserve generally experiences mild weather year-round due to its proximity to the ocean, making it suitable for running in most seasons. However, it can be quite windy at the top, so layering is advisable. Trails can be muddy after winter storms, so spring through fall often offer the most comfortable conditions.
The area is highly rated by the komoot community, with an average score of 4.8 stars from over 15 reviews. Runners often praise the diverse landscapes, from shaded forests to open grassland ridges, and the spectacular panoramic views of the San Francisco Bay and Pacific Ocean. The extensive and well-maintained trail network also receives high marks for offering variety for all fitness levels.
Yes, Windy Hill Open Space Preserve is home to diverse ecosystems, including woodlands, grasslands, and chaparral, which support a rich variety of plant and animal species. While jogging, you might spot deer, foxes, coyotes, and numerous bird species, especially during quieter times of the day.
The preserve opens one hour before sunrise and closes one hour after sunset. This allows for early morning or late afternoon runs, letting you take advantage of cooler temperatures and beautiful light.


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