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United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

Routes
MTB trails
United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

The best MTB trails in 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.

Best mountain bike trails in Windy Hill Open Space Preserve (Closed Areas)

  • The most popular mountain bike…

Last updated: June 24, 2026

5.0

(1)

6

riders

#1.

Woodside Store (Historic Site) – Skeggs Point loop from Portola Valley

40.1km

03:18

960m

960m

Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary.

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Hard

Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary. Some portions of the route may require you to push your bike.

Hard
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Hard mountain bike ride. Good fitness required. Advanced riding skills necessary. Some portions of the route may require you to push your bike.

Hard

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

Easy

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

Easy
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Popular around Windy Hill Open Space Preserve (Closed Areas)

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Tips from the Community

RalphGrundler
April 4, 2026, White Oak Trail

Make sure White Oak trail is open before you go.

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Alise’s Restaurant is a popular spot for both cyclists and motorcyclists. The food is good, the staff is known for being friendly, and the place has a laid-back, welcoming vibeβ€”perfect for a post-ride meal or coffee break.

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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 loop’s rolling, paved trails. From here, you’ll begin with a gentle incline through open hillsides, quickly gaining elevation and views of the Santa Cruz Mountains. It’s a scenic entry with fewer crowds than the main Stanford Avenue gate. Like the rest of the Dish area, it’s open only to walkers, runners, and hikersβ€”no 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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Nitram X2
March 16, 2025, Borel Hill

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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Sue
December 31, 2024, Rossotti's Alpine Inn

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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Frequently Asked Questions

What are the difficulty levels of mountain bike trails in Windy Hill Open Space Preserve?

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.

What is the typical length of mountain bike trails in Windy Hill Open Space Preserve?

Trail lengths vary significantly. For example, an easy route like the Redtail Loop Trail – 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) – Skeggs Point loop from Portola Valley, can extend to nearly 25 miles (40 km).

Are there mountain bike trails suitable for beginners in Windy Hill Open Space Preserve?

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 – Arastradero Lake loop from Enid Pearson-Arastradero Preserve, which is an easy 5.7 miles (9.2 km) trail.

Where can I find challenging mountain bike routes in Windy Hill Open Space Preserve?

For experienced riders seeking a challenge, Windy Hill Open Space Preserve offers 13 difficult routes. Consider the Old Ranch Trail – White Oak Trail loop from Portola Valley, a demanding 24.2 miles (38.9 km) route with over 1,000 meters of elevation gain.

Are dogs allowed on mountain bike trails in Windy Hill Open Space Preserve?

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.

What is the best time of year for mountain biking in Windy Hill Open Space Preserve?

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.

Are there any loop mountain bike trails in Windy Hill Open Space Preserve?

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 – Arastradero Lake loop from Portola Valley is another great option.

What do other mountain bikers enjoy the most about mountain biking in Windy Hill Open Space Preserve?

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.

How many mountain bike trails are there in Windy Hill Open Space Preserve?

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.

Are there any viewpoints along the mountain biking routes in Windy Hill Open Space Preserve?

Yes, many routes offer scenic views of the surrounding Bay Area. The Woodside Store (Historic Site) – Skeggs Point loop from Portola Valley, for instance, is known for its panoramic views from Skeggs Point.

Is public transport available to access Windy Hill Open Space Preserve for mountain biking?

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.

What kind of wildlife can I expect to see while mountain biking in Windy Hill Open Space Preserve?

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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