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Routes
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United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

Routes
Cycling routes
United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

The best cycling routes in Windy Hill Open Space Preserve (Closed Areas)

4.6

(106)

2,991

riders

85

rides

Touring cycling in Windy Hill Open Space Preserve (Closed Areas) offers routes through diverse landscapes and varied terrain. The preserve is characterized by its "naked" peninsula range, providing expansive panoramic views of the San Francisco Bay and Santa Cruz Mountains. Elevations rise to 1905 feet (581 m), presenting challenging climbs and descents for cyclists. The area features a network of trails suitable for gravel biking, winding through woodlands, grasslands, and chaparral ecosystems.

Best touring cycling routes in Windy Hill Open…

Last updated: May 13, 2026

5.0

(1)

22

riders

#1.

Portola Road – Woodside Store (Historic Site) loop from Enid Pearson-Arastradero Preserve

26.3km

01:35

210m

210m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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

Hiking in Windy Hill Open Space Preserve (Closed Areas)

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MTB Trails in Windy Hill Open Space Preserve (Closed Areas)

Road Cycling Routes in Windy Hill Open Space Preserve (Closed Areas)

Gravel biking in Windy Hill Open Space Preserve (Closed Areas)

Tips from the Community

Lisa
June 22, 2025, Old Woodside Store Museum

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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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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This is where La Ronda Road meets Skyline Boulevard. After the climb, it’s 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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Will
June 20, 2025, Alpine Road

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 large complex is home to City Hall, the main library, and it adjoins Burgess Park. The pond, fountain, and other landscaping touches make it a great place to visit.

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Zachary
January 23, 2025, El Palo Alto Park

This great little park along San Francisco Creek features El Palo Alto tree, the redwood for which the city was named. The trail is paved and shared with other hikers.

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Zachary
January 23, 2025, Woodside

Woodside is a historic town-turned upscale community along the old wagon path from San Francisco to Santa Clara. The downtown is a great place to take a break from your ride and features a few quaint shops, a market, bakery, and outdoor seating.

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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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Frequently Asked Questions

How many touring cycling routes are available in Windy Hill Open Space Preserve?

Windy Hill Open Space Preserve offers a wide selection of touring cycling routes, with over 70 options to explore. These routes cater to various skill levels, including 15 easy, 36 moderate, and 22 difficult paths.

What kind of terrain can I expect when touring cycling in Windy Hill Open Space Preserve?

The preserve features diverse terrain, including woodlands, grasslands, and chaparral ecosystems. You'll encounter varied surfaces suitable for gravel biking, with elevations rising to 1905 feet (581 m), offering challenging climbs and descents. The region is known for its 'naked' (not forested) peninsula range, providing unique visual landscapes.

Are there any challenging touring cycling routes for experienced riders?

Yes, for experienced touring cyclists seeking a challenge, there are 22 difficult routes. One such option is the Old La Honda Road – Portola Valley loop from Enid Pearson-Arastradero Preserve, which features significant elevation changes over its 23.3 km distance.

What are the best routes for moderate touring cyclists?

Moderate touring cyclists have a wide array of choices, with 36 routes available. A popular option is the Dwight Crowder Path – Rossotti's Alpine Inn loop from Los Trancos Woods, covering 18.4 km with moderate elevation gain, offering a rewarding ride.

What do other touring cyclists enjoy most about the routes in Windy Hill Open Space Preserve?

The touring cycling routes in Windy Hill Open Space Preserve are highly rated by the komoot community, with an average score of 4.6 stars from over 110 reviews. Cyclists often praise the stunning panoramic views of the San Francisco Bay and Santa Cruz Mountains, as well as the diverse ecosystems and varied terrain that make each ride unique.

Are there any circular touring cycling routes in the preserve?

Yes, many routes in Windy Hill Open Space Preserve are designed as loops, allowing you to start and end at the same point. An example is the Portola Road – Woodside Store (Historic Site) loop from Enid Pearson-Arastradero Preserve, a moderate 27.4 km route that offers varied terrain and scenic views.

What natural features or landmarks can I see along the touring cycling routes?

The preserve is renowned for its breathtaking panoramic vistas of the San Francisco Bay, Stanford University, and the Santa Cruz Mountains. You'll also experience diverse ecosystems, including woodlands, grasslands, and chaparral. During spring and fall, the area is vibrant with wildflowers, adding to its scenic appeal. The preserve's unique 'naked' appearance, rising to 1905 ft (581 m), is a landmark in itself.

What is the best time of year to go touring cycling in Windy Hill Open Space Preserve?

While specific seasonal recommendations for touring cycling are not detailed, the preserve is particularly vibrant with wildflowers during spring and fall. Cyclists should be prepared for potentially windy conditions, as suggested by the preserve's name, regardless of the season.

Are there any routes that offer views of the San Francisco Bay?

Absolutely. Windy Hill Open Space Preserve is famous for its stunning panoramic views of the San Francisco Bay. Many routes, especially those ascending to higher elevations, will reward you with expansive vistas. The preserve's unique position as the 'naked' part of the peninsula range ensures unobstructed views.

Can I find routes that pass through different ecosystems?

Yes, the preserve is characterized by its diverse ecosystems. Routes often wind through woodlands, grasslands, and chaparral, providing a varied and interesting cycling experience. The Rossotti's Alpine Inn – Los Altos-Palo Alto Bike Trail loop from Enid Pearson-Arastradero Preserve, for instance, leads through diverse ecosystems and offers panoramic vistas.

What is the elevation gain like on the touring cycling routes?

The preserve features significant elevation changes, with its summit reaching 1905 feet (581 m). Cyclists can expect challenging climbs and rewarding descents. For example, the Alpine Road loop from Enid Pearson-Arastradero Preserve involves an elevation gain of over 215 meters, providing a good workout.

Most popular routes in Windy Hill Open Space Preserve (Closed Areas)

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