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United States
California
San Mateo County

Windy Hill Open Space Preserve

The best running trails in Windy Hill Open Space Preserve

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.

Best jogging routesโ€ฆ

Last updated: June 26, 2026

4.5

(2)

67

runners

#1.

Windy Hill Summit loop from Portola Valley

16.7km

02:13

490m

490m

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

9

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Hard run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(1)

11

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Andrus

Tips from the Community

Rama
June 30, 2025, Windy Hill Summit

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, thereโ€™s a small bench tucked under eucalyptus trees where you get a clear view of Mt. Diablo. Itโ€™s a good spot to pause, catch your breath, and take in the landscape.

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From up here on the ridge you get great sweeping views across the foothills. On a clear day you can see out west to the Pacific Ocean.

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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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Nitram X2
March 16, 2025, Borel Hill

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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Alex
September 15, 2024, Windy Hill Summit

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. Itโ€™s a great spot to watch the sunset and take in views.

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AverieOutside
December 21, 2023, Borel Hill

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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Frequently Asked Questions

How many running routes are available in Windy Hill Open Space Preserve?

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.

What kind of terrain can I expect when jogging in Windy Hill Open Space Preserve?

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.

Are there loop trails suitable for running in Windy Hill Open Space Preserve?

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.

Are there jogging routes for beginners or those looking for an easier run?

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.

What are some challenging running routes for experienced joggers?

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.

What kind of views can I expect along the running trails?

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.

Are there any notable landmarks or points of interest to see while jogging?

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.

Is Windy Hill Open Space Preserve suitable for dog-friendly running?

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.

What is the best time of year to go running in Windy Hill Open Space Preserve?

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.

What do other runners enjoy the most about jogging in Windy Hill Open Space Preserve?

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.

Are there any running routes that offer good opportunities for wildlife spotting?

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.

What are the operating hours for Windy Hill Open Space Preserve?

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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