5.0
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Gravel biking in Windy Hill Open Space Preserve offers diverse terrain across over 1,300 acres, climbing from Portola Valley to the Skyline Ridge. The preserve features open grassland ridges, lush oak woodlands, and forests of redwood, fir, and oak. Riders can expect varied surfaces and elevation gains up to 3,000 feet, making it suitable for different fitness levels. The distinctive, breezy, grass-covered hilltop is a prominent feature of the landscape.
Last updated: May 17, 2026
5
riders
30.8km
02:01
550m
550m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
riders
48.1km
03:34
1,170m
1,170m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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4
riders
48.2km
03:59
1,300m
1,300m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
13.9km
01:13
440m
440m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
65.1km
04:51
1,560m
1,560m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Windy Hill Open Space Preserve
Enid Pearson-Arastradero Preserve offers rolling grasslands mixed with oak and evergreen trees. The trail system starts on pavement and transitions to packed dirt and gravel—great for bikes with wider tires or a solid gravel setup. Keep an eye out for deer, coyotes, and even bobcats, and take a moment to pause at one of the benches or by Arastradero Lake to enjoy the open views.
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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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Didn’t OLR used to turn into Dirt before reaching Skyline? Is it all pavement now?? Scott
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Black Mountain, situated on Monte Bello Ridge, is a popular destination for hikers and mountain bikers. With an elevation of 2,812 feet, it's easy to understand why. From the summit, the views of the Santa Cruz Mountains and Silicon Valley are breathtaking.
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This fantastic tavern, founded in 1852, is the second oldest in the state. It features a large, beer garden-style outdoor area with plenty of shade. An extensive beer and food menu makes it a perfect stop to enjoy a brew and some great food after a ride.
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From Elena Road, you’ll be treated to breathtaking views of the bay and surrounding hills. The vantage point offers a peaceful scene of the landscape, showcasing the natural beauty of the Bay Area.
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Great place for a break in a beautiful, peaceful spot among the redwoods. The restaurant is popular with locals, motorcyclists, hikers, and cyclists, and is the perfect place for a cold drink after finishing the climb up.
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Windy Hill Open Space Preserve offers a good selection of gravel bike trails. There are 9 routes documented on komoot, ranging from moderate to difficult, providing diverse options for your ride.
You can expect diverse terrain, transitioning through open grassland ridges, lush oak woodlands, and forests of redwood, fir, and oak. Some trails are mostly paved, while others offer challenging climbs and varied surfaces. The preserve is known for its distinctive, breezy, grass-covered hilltop.
Yes, Windy Hill Open Space Preserve caters to various fitness and skill levels. The trails range from moderate to difficult, with elevation gains up to 3,000 feet, ensuring options for those seeking a good workout as well as less strenuous rides. For example, the Old La Honda Road – Portola Road loop from Portola Valley is a moderate option, while the Old La Honda Road – West Old La Honda Road loop from Portola Valley is considered difficult.
Bicycles are restricted to designated trails only, with a 15 mph speed limit (5 mph when passing). It's important to note that e-bikes are generally not allowed on most Midpeninsula Regional Open Space District trails. Additionally, some specific trails like Betsy Crowder, Razorback, Lost, and Hamms Gulch are closed to bicycles year-round.
The preserve offers breathtaking panoramic views of the San Francisco Bay, Stanford University, Mount Tamalpais, Mount Diablo, and even the Pacific Ocean on clear days, especially from the Windy Hill Summit and upper portions. You can also visit Windy Hill Open Space Preserve Scenic View. Sausal Pond is another significant attraction, home to various wildlife and offering scenic picnic areas.
While the preserve offers multiuse trails, many gravel routes feature significant elevation gains and are rated moderate to difficult. For family-friendly options, it's best to check individual route descriptions for flatter sections or shorter loops. The preserve's general trail system is multiuse, but specific gravel routes might be challenging for younger riders.
Spring is particularly beautiful, as the open grassy meadows are adorned with wildflowers. Clear days offer the best panoramic views of the Bay Area and Pacific Ocean. The preserve's namesake 'Windy Hill' suggests it can be breezy, so checking weather conditions is always advisable.
Yes, certain trails are closed to bicycles year-round. These include Betsy Crowder, Razorback, Lost, and Hamms Gulch trails. Always ensure you are on designated multiuse trails open to bikes.
The preserve has various access points, including trailheads in Portola Valley. Parking is typically available at these designated trailheads. It's advisable to check specific trailhead information for the route you plan to ride to confirm parking availability and any potential fees.
The komoot community frequently praises the diverse terrain, from open grasslands to lush woodlands, and the stunning panoramic views of the San Francisco Bay and beyond. Riders appreciate the variety of routes catering to different fitness levels and the sense of isolation despite the preserve's proximity to urban areas.
While popular, the preserve spans over 1,300 acres, offering many miles of trails. To find less crowded routes, consider exploring some of the less frequently mentioned trails or visiting during off-peak hours, such as early mornings on weekdays. The White Oak Trail – Bella Vista Trail loop from Los Trancos Open Space Preserve might offer a different experience.
The preserve is located near Portola Valley, which offers local amenities. You can find cafes and other eateries in Portola Valley for refreshments before or after your ride.


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