4.8
(78)
2,217
riders
19
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Touring cycling in Windy Hill Open Space Preserve offers routes through diverse landscapes, including open grassland ridges and forests of redwood, fir, and oak. The preserve spans over 1,100 acres in San Mateo County, California, featuring a prominent, breezy hilltop. At 1,905 feet (581 m), the summit of Windy Hill provides panoramic views across Stanford University to the San Francisco Bay and the Pacific Ocean on clear days. The area features a network of multiuse trails, many of which are…
Last updated: May 14, 2026
13
riders
11.4km
00:45
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
riders
18.4km
01:16
330m
330m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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8
riders
8.62km
00:49
180m
180m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
26
riders
24.8km
01:56
650m
650m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
12
riders
Moderate bike ride. 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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The Northern part of Alpine Road is a paved and curvy descent through wooded areas and runs parallel to Coal Mine Ridge Preserve, eventually connecting with the trailhead there.
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This mostly paved bike trail alongside Alpine Road is great for bike commuting — just don't run over any slower trail users! The trail runs all the way from Portola Valley to Stanford, offering some nice shade along the way. The brief moments of unpaved trail are near the Portola Valley end.
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Just right off the picnic bench area lies a viewpoint of the Pearson-Arastradero Preserve. An open meadow offers views of the preserve and surrounding mountains. It's a nice shaded area for a break!
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Page Mill Road is a classic route for cyclists looking for a challenge, with its steep climbs, sharp switchbacks, and stunning views of Silicon Valley. Starting near Palo Alto and climbing into the Santa Cruz Mountains, the ride tests your legs but rewards you with breathtaking scenery. Be prepared for varying gradients, especially in the lower sections, and pack plenty of water—the climb can be intense, especially on warmer days.
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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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Sobey Pond is a tranquil oasis nestled along the Arastradero Creek Trail, with its still waters reflecting the surrounding verdant trees. This pristine pond serves as an integral water source for the diverse array of animals who call the preserve their home, with lush vegetation that enhances the area's natural beauty.
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Arastradero Lake is a quiet pond in the hills of the Arastradero Preserve. The lake is surrounded by oak trees and can get pretty dry in summer.
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Komoot features nearly 20 no-traffic touring cycling routes in and around Windy Hill Open Space Preserve. These routes offer a variety of experiences, with 2 easy, 13 moderate, and 4 difficult options to choose from.
The preserve features a mix of fire roads and multi-use trails, which are generally suitable for touring cycling. You can expect surfaces ranging from paved sections to well-maintained dirt or gravel paths. Some routes, like the Dwight Crowder Path – Rossotti's Alpine Inn loop from Los Trancos Woods, offer a smooth experience, while others might involve more varied terrain. Always check current conditions, especially after rain, as some trails may have restrictions.
Windy Hill Open Space Preserve offers diverse terrain, from open grassland ridges to lush forests of redwood, fir, and oak. Routes often feature ascents and descents, providing a good workout. For example, the Old La Honda Road – Portola Valley loop from Enid Pearson-Arastradero Preserve includes over 500 meters of elevation gain, while the Bowl Loop Jumps – Sobey Pond loop from Enid Pearson-Arastradero Preserve has a more modest 175 meters. The prominent breezy hilltop at 1,905 feet (581 m) ensures panoramic views but also means some significant climbs.
Yes, cyclists must adhere to specific regulations. Bicycles are allowed on designated multi-use trails, and helmets are required. There is a speed limit of 15 mph, which reduces to 5 mph when passing others. E-bikes are generally not permitted on most trails. It's always a good idea to check for any temporary trail closures or specific rules before your ride.
While many routes in Windy Hill Open Space Preserve involve significant elevation, there are easier options suitable for families or beginners. Komoot lists 2 easy touring cycling routes. Look for routes with lower elevation gain and shorter distances, which can often be found in the lower portions of the preserve or on less strenuous fire roads. Always check the route details for specific difficulty and terrain before heading out with children.
The preserve is renowned for its stunning vistas. The Windy Hill Summit offers magnificent 360-degree panoramic views of the San Francisco Bay, Stanford University, Mount Tamalpais, and Mount Diablo. Other scenic spots include the Windy Hill Open Space Preserve Scenic View. You might also pass through areas near Portola Valley, a charming settlement.
The area is highly rated by the komoot community, with an average score of 4.75 stars from 67 ratings. Reviewers often praise the quiet, traffic-free nature of the trails, the diverse landscapes ranging from open grasslands to redwood forests, and the spectacular panoramic views from the higher elevations. The well-maintained fire roads and multi-use trails are also frequently highlighted for their suitability for touring bikes.
Yes, many of the no-traffic touring cycling routes in Windy Hill Open Space Preserve are designed as loops, allowing you to start and end at the same point. Examples include the Alpine Road loop from Enid Pearson-Arastradero Preserve and the Old La Honda Road – Old La Honda Road loop from Jasper Ridge Biological Preserve. These loops provide a comprehensive experience of the preserve's varied ecosystems and views without needing to retrace your path.
Public transport options directly to the preserve are limited. Most visitors arrive by car, utilizing the parking areas available at both the lower portion on Portola Road and the upper Spring Ridge parking area on Skyline Boulevard. It's advisable to plan your transport in advance, as bus routes in the immediate Portola Valley area may not directly serve the preserve entrances.
Spring and fall are generally considered the best times for touring cycling in Windy Hill Open Space Preserve. In spring, the open, grassy meadows are adorned with beautiful wildflowers, and the weather is typically mild. Fall offers pleasant temperatures and clear skies. While summer can be enjoyable, the preserve's location means summer fog often spills over Skyline Ridge, creating cooler, lush conditions in some areas, but also potential for less visibility. Winters can bring wet conditions, which may lead to trail closures or muddy sections.
While the preserve itself is a natural area, the nearby Portola Valley offers a few options for cafes and restaurants where you can refuel before or after your ride. It's a good idea to check their operating hours in advance, especially if you plan to visit on a weekday or during off-peak seasons.


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