Windy Hill Open Space Preserve (Closed Areas)
Windy Hill Open Space Preserve (Closed Areas)
4.8
(89)
1,167
riders
48
rides
Mountain biking in Windy Hill Open Space Preserve (Closed Areas) offers a diverse landscape for riders. The preserve features rolling hills, dense woodlands, and open grasslands, providing varied terrain for mountain bike trails. Riders can expect a mix of challenging climbs and flowing descents through natural environments. The area is characterized by its elevation changes and scenic views of the surrounding Bay Area.
Last updated: June 24, 2026
5.0
(1)
6
riders
40.1km
03:18
960m
960m
Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary.
5.0
(4)
38
riders
38.9km
04:33
1,080m
1,080m
Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary. Some portions of the route may require you to push your bike.

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5.0
(7)
35
riders
28.3km
03:25
650m
650m
Hard mountain bike ride. Good fitness required. Advanced riding skills necessary. Some portions of the route may require you to push your bike.
3
riders
19.6km
01:12
230m
230m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.
4.9
(9)
28
riders
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.
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The Stanford Dish Trail parking area off Alpine Road (near Piers Lane and just west of Junipero Serra Boulevard) serves as a quieter but still well-used western entrance to the Dish hiking area. This access point offers a small parking lot and connects directly to the Dish loopβs rolling, paved trails. From here, youβll begin with a gentle incline through open hillsides, quickly gaining elevation and views of the Santa Cruz Mountains. Itβs a scenic entry with fewer crowds than the main Stanford Avenue gate. Like the rest of the Dish area, itβs open only to walkers, runners, and hikersβno dogs, no bikes. Come prepared for sun exposure and some steep grades.
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This mostly paved bike trail alongside Alpine Road is great for bike commuting β 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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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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Here, the Steve's Creek Nature Trail and the Canyon Trail intersect. A lovely patch of grass surrounds the junction, making it an ideal spot for a break.
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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 a range of mountain bike trails catering to different skill levels. You'll find 11 easy routes, 13 moderate routes, and 13 difficult routes, providing options for beginners to experienced riders.
Trail lengths vary significantly. For example, an easy route like the Redtail Loop Trail β Arastradero Lake loop from Enid Pearson-Arastradero Preserve is about 5.7 miles (9.2 km). More challenging routes, such as the Woodside Store (Historic Site) β Skeggs Point loop from Portola Valley, can extend to nearly 25 miles (40 km).
Yes, there are several trails suitable for beginners. The preserve features 11 easy routes. A good option to start with is the Redtail Loop Trail β Arastradero Lake loop from Enid Pearson-Arastradero Preserve, which is an easy 5.7 miles (9.2 km) trail.
For experienced riders seeking a challenge, Windy Hill Open Space Preserve offers 13 difficult routes. Consider the Old Ranch Trail β White Oak Trail loop from Portola Valley, a demanding 24.2 miles (38.9 km) route with over 1,000 meters of elevation gain.
Policies regarding dogs in open space preserves can vary. It's always best to check the official Midpeninsula Regional Open Space District website or trailhead signage for the most current regulations on where dogs are permitted and if they need to be on a leash.
The Bay Area generally offers good mountain biking conditions year-round. However, spring and fall often provide the most pleasant temperatures. Summers can be warm, and winters might bring rain, affecting trail conditions. Always check local weather and trail status before heading out.
Yes, many of the mountain bike routes in the preserve are loops. For example, the Stevens Creek Nature Trail loop from Enid Pearson-Arastradero Preserve is a popular 17.3 miles (27.8 km) loop, and the Bowl Loop Jumps β Arastradero Lake loop from Portola Valley is another great option.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 100 reviews. Riders often praise the diverse landscape, which includes rolling hills, dense woodlands, and open grasslands, as well as the varied terrain offering both challenging climbs and flowing descents.
There are over 35 mountain bike routes available in Windy Hill Open Space Preserve, offering a wide variety of experiences for riders of all levels.
Yes, many routes offer scenic views of the surrounding Bay Area. The Woodside Store (Historic Site) β Skeggs Point loop from Portola Valley, for instance, is known for its panoramic views from Skeggs Point.
While public transport options might be limited directly to all trailheads, some regional transit services may connect to areas near the preserve. It's advisable to check local bus schedules or consider ride-sharing services to reach specific access points.
Windy Hill Open Space Preserve is home to diverse wildlife. Riders might spot deer, various bird species, and smaller mammals. Keep an eye out, especially during quieter times of day, and always maintain a respectful distance.


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