4.6
(152)
7,012
riders
43
rides
Road cycling in Windy Hill Open Space Preserve is characterized by its diverse terrain, ranging from breezy, grass-covered hilltops to redwood, fir, and oak forests. The preserve encompasses the eastern side of Skyline Ridge, ascending to a 1,905-foot summit, providing panoramic views of the San Francisco Bay and Pacific Ocean. Cyclists can navigate open grassland ridges, oak woodlands, and grassy meadows, with varied ecosystems offering different challenges and scenic backdrops. The area features a network of trails and fire roads…
Last updated: April 27, 2026
5.0
(2)
131
riders
25.0km
01:30
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
14
riders
15.1km
01:00
420m
420m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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3.0
(1)
6
riders
14.7km
00:47
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
12
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
6
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Windy Hill Open Space Preserve
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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Didn’t OLR used to turn into Dirt before reaching Skyline? Is it all pavement now?? Scott
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Woodside Store was built back in the 1850s by two pioneers who came to California for the gold rush. At the time it was the only stagecoach stop between San Francisco and Santa Clara, and it carried all the essential items that travelers riding between cities might need. The store has been restored, inside and out, to look exactly as it did centuries ago. You can call the museum ahead of your trip to book tours.
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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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Old La Honda Rd downhill video: https://youtu.be/icnBpBZQ8gE?si=xYovaH-Nr8llwLEM
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The Woodside Store, also known as Tripp Store, is located at 3300 Tripp Road at Kings Mountain Road in Woodside, San Mateo County, California. It has been listed on the National Register of Historic Places since 1985 and was designated a California Historical Landmark in 1949. The store's history dates back to October 1849 when Matthias Alfred Parkhurst purchased land in the area and began a shingle-making and lumber business with his partners, including Robert Orville Tripp. The store was established in 1853, originally serving the needs of lumbermen and settlers during the Gold Rush era. Dr. Tripp became the sole operator of the store after Parkhurst's death in 1863, running it until his own death in 1909. He was a well-known figure in Woodside, holding various public offices. The San Mateo County Historical Association acquired the store in the 1940s, and it was restored to its 1880s condition by 1994.
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Road cycling in Windy Hill Open Space Preserve offers a diverse experience. You'll encounter breezy, grass-covered hilltops, as well as sections through redwood, fir, and oak forests. The preserve features open grassland ridges, oak woodlands, and grassy meadows, providing varied ecosystems and scenic backdrops. While some sections can be steep, many lower trails are fire roads suitable for cycling.
The preserve offers a range of routes catering to different skill levels. You can find easy loops, moderate paths, and more challenging climbs. For instance, the Manzanita Way – Tree Tunnel on Portola Road loop from Portola Valley is considered easy, while routes like Old La Honda Road – Manzanita Way loop from Portola Valley are moderate, involving notable climbs and descents.
Road cycling in Windy Hill Open Space Preserve offers stunning panoramic views. From elevated points, especially the 1,905-foot summit, you can enjoy 360-degree vistas of both the San Francisco Bay and the Pacific Ocean. On clear days, you might even spot Stanford University, Mount Tamalpais, and Mount Diablo. The preserve's diverse trails also allow you to cycle through beautiful forested landscapes and open, grassy areas.
Yes, Windy Hill Open Space Preserve is rich in natural features and viewpoints. You can experience the distinctive, breezy, grass-covered hilltop, and cycle through areas with old-growth Douglas-Fir trees. Notable points include the Windy Hill Summit and the Windy Hill Open Space Preserve Scenic View. Sausal Pond is also a key natural feature, providing habitat for various wildlife.
Yes, parking is available. The Anniversary Trail, for example, connects two parking areas on Skyline Boulevard, providing convenient access for cyclists.
The preserve is known for its breezy conditions, which can be pleasant. Spring is particularly beautiful, as the grassy meadows burst with wildflowers. The area is often nourished by summer fog spilling over Skyline Ridge, contributing to a lush environment. The preserve opens a half-hour before sunrise and closes a half-hour after sunset, allowing ample time for rides throughout the day.
While some sections can be steep, the preserve offers a variety of trail types, including easier fire roads, that can be suitable for families. Routes like the Manzanita Way – Tree Tunnel on Portola Road loop from Portola Valley are rated as easy and lead through pleasant oak woodlands and open spaces.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 150 reviews. Reviewers often praise the diverse terrain, from open grasslands to redwood forests, and the stunning panoramic views of the San Francisco Bay and Pacific Ocean from the ridge tops.
There are over 35 road cycling routes available in Windy Hill Open Space Preserve, offering a wide range of options for different preferences and skill levels.
Yes, many of the road cycling routes in Windy Hill Open Space Preserve are designed as loops. Examples include the Rossotti's Alpine Inn – Junipero Serra Boulevard loop from Los Trancos Woods and the Tree Tunnel on Portola Road – Lower Kings Mountain Road loop from Portola Valley, allowing cyclists to start and finish at the same point.
Absolutely. Windy Hill Open Space Preserve is known for its ascents, with the preserve encompassing the eastern side of Skyline Ridge and reaching a 1,905-foot summit. Routes like the Old La Honda Road – Old La Honda Road loop from Portola Valley offer over 400 meters of elevation gain, providing a good challenge for road cyclists.


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