4.7
(93)
2,342
riders
45
rides
Touring cycling in Windy Hill Open Space Preserve offers routes through a landscape characterized by rolling hills and open grasslands, providing expansive views of the surrounding area. The preserve features varied terrain, including paved roads and dedicated bike trails, with elevations that present moderate climbs. These routes often connect to nearby historic sites and natural areas, making for diverse cycling experiences.
Last updated: August 5, 2026
61
riders
28.6km
02:02
550m
550m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
21
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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11
riders
11.4km
00:45
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
17.9km
01:15
320m
320m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4
riders
18.8km
01:20
350m
350m
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
Once upon a time this was the only general store in this area, serving not only as a general-purpose retailer but also the post office, bank, and informal dentist's office. Nowadays it's a museum, staffed by docents ready to offer drop-in history lessons.
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This is where La Ronda Road meets Skyline Boulevard. After the climb, itโs the perfect place to recharge and grab something to eat at one of the nearby restaurants or grocery stores. Alise's Restaurant is a popular one.
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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 โ 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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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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Windy Hill Open Space Preserve offers nearly 40 touring cycling routes. These routes vary in difficulty, with 7 easy, 19 moderate, and 12 difficult options, providing diverse experiences for cyclists.
Yes, there are several routes suitable for beginners. The preserve features 7 easy touring cycling routes, which are generally shorter and have less elevation gain, making them ideal for those new to touring cycling or looking for a relaxed ride.
Many of the touring cycling routes in Windy Hill Open Space Preserve are designed as loops, allowing you to start and end at the same point. For example, the Portola Road โ Woodside Store (Historic Site) loop from Enid Pearson-Arastradero Preserve is a popular circular option.
Common starting points for many routes, such as the Enid Pearson-Arastradero Preserve, typically offer parking facilities. It's advisable to check specific route details on komoot for recommended parking areas near your chosen starting point.
Along the touring cycling routes, you can enjoy expansive views of the surrounding area, including the Windy Hill Open Space Preserve Scenic View. Other notable attractions include the historic Woodside Store, which is passed by on the Portola Road โ Woodside Store (Historic Site) loop, and the Windy Hill Summit itself, offering panoramic vistas.
The preserve is enjoyable year-round, but spring and fall offer the most pleasant conditions with mild temperatures and lush landscapes. Summers can be warm, especially in open areas, while winters are generally mild but may bring occasional rain.
Dogs are generally permitted on leash on designated trails within Windy Hill Open Space Preserve. However, specific regulations can vary, so it's always best to check the official Midpeninsula Regional Open Space District website for the most current rules regarding pets on trails.
Many of the moderate and easy routes are suitable for families, especially those with some cycling experience. The varied terrain and dedicated bike paths, such as those found on the Rossotti's Alpine Inn โ Los Altos-Palo Alto Bike Trail loop, offer enjoyable rides for different skill levels.
Windy Hill Open Space Preserve is home to diverse wildlife. Cyclists might spot deer, various bird species including raptors, and smaller mammals. Keep an eye out, especially during dawn and dusk, for opportunities to observe local fauna.
The preserve features varied terrain, from paved roads to dedicated bike trails, with rolling hills and moderate climbs. Conditions can change, so layers are recommended. Wear appropriate cycling attire, bring sun protection, and carry enough water, especially on longer routes or warmer days.
While the preserve itself is natural open space, the surrounding towns like Portola Valley and Woodside offer various cafes and eateries where you can refuel before or after your ride. Some routes, like the Dwight Crowder Path โ Rossotti's Alpine Inn loop, pass by establishments like Rossotti's Alpine Inn.
Windy Hill Open Space Preserve is known for its expansive open grasslands, rolling hills, and panoramic views, often featuring more exposed terrain. Huddart Park, by contrast, is typically more forested with shadier trails. Both offer varied cycling experiences, but Windy Hill provides a distinct open-space feel.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 60 reviews. Reviewers often praise the stunning panoramic views, the well-maintained trails, and the challenging yet rewarding climbs that offer a great workout amidst beautiful scenery.


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