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Routes
Road cycling routes
United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

Routes
Road cycling routes
United States
California
San Mateo County

Windy Hill Open Space Preserve (Closed Areas)

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

4.6

(255)

10,852

riders

79

rides

Road cycling in Windy Hill Open Space Preserve (Closed Areas) offers routes through varied terrain in San Mateo County. The preserve features extensive open grassland ridges that provide panoramic views of the San Francisco Bay and the Pacific Ocean. Beyond the open areas, the landscape transitions into forests of redwood, fir, and oak. The elevation changes significantly, with routes climbing from Portola Valley to Skyline Ridge, presenting both moderate gradients and notable climbs for road cyclists.

Best road cycling routes…

Last updated: August 5, 2026

5.0

(2)

119

riders

#1.

Portola Valley – Old La Honda Road loop from Portola Valley

31.8km

01:45

660m

660m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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

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Tips from the Community

maniboyflex
June 20, 2025, Alice's Restaurant at La Honda and Skyline Junction

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 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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Didn’t OLR used to turn into Dirt before reaching Skyline? Is it all pavement now?? Scott

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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.

2

0

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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Great place for a break in a beautiful, peaceful spot among the redwoods. The restaurant is popular with locals, motorcyclists, hikers, and cyclists, and is the perfect place for a cold drink after finishing the climb up.

1

0

Old La Honda Rd downhill video: https://youtu.be/icnBpBZQ8gE?si=xYovaH-Nr8llwLEM

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51m
December 7, 2023, Old La Honda Road

3 miles of great winding mountain road. It ascends from the Palo Alto side up to the Skyline road. Quite narrow in places and fairly steep, but only light car use means this is a fun road climb.

2

0

Frequently Asked Questions

What are the difficulty levels of road cycling routes in Windy Hill Open Space Preserve?

Windy Hill Open Space Preserve offers a variety of road cycling routes catering to different skill levels. You'll find approximately 28 easy routes, 33 moderate routes, and 13 more challenging routes. For an easy ride, consider the Portola Valley – Rossotti's Alpine Inn loop from Enid Pearson-Arastradero Preserve. If you're looking for a moderate challenge, the Old La Honda Road – Manzanita Way loop from Portola Valley includes a notable climb.

What are the typical distances for road cycling routes in the preserve?

Road cycling routes in Windy Hill Open Space Preserve vary in length. For example, the Portola Valley – Rossotti's Alpine Inn loop is about 12 miles (19.2 km), while the Old La Honda Road – Manzanita Way loop extends to 20.2 miles (32.4 km). Many routes fall within this range, offering options for shorter spins or longer excursions.

Where can road cyclists park when visiting Windy Hill Open Space Preserve?

Many popular road cycling routes in the area, such as those starting from Portola Valley, typically have public parking available near their trailheads or designated starting points. It's always advisable to check local signage for specific parking regulations and availability before your ride.

Are there any family-friendly road cycling alternatives near Windy Hill Open Space Preserve?

While some routes within the preserve offer gentle gradients suitable for families, such as the Portola Valley – Rossotti's Alpine Inn loop, families might also enjoy exploring nearby areas with dedicated bike paths or quieter roads. The preserve's rolling hills and open vistas provide a scenic backdrop for rides of varying difficulty.

What is the best season for road biking in Windy Hill Open Space Preserve?

The region generally offers pleasant road cycling conditions for much of the year. Spring and fall often provide mild temperatures and clear skies, making them ideal. Summer can be warm, especially in the open areas, while winter might bring occasional rain. Always check the weather forecast before heading out.

Are there any cycling-friendly cafes or stops near the preserve?

The towns surrounding Windy Hill Open Space Preserve, particularly Portola Valley, offer various cafes and eateries where cyclists can refuel. These spots are often popular meeting points for local riders before or after their routes.

Which routes offer the most scenic viewpoints in the Windy Hill Open Space Preserve area?

Many routes in the preserve provide scenic vistas due to its open spaces and rolling hills. Routes that include climbs, like sections of the Old La Honda Road – Manzanita Way loop, often reward cyclists with expansive views of the surrounding landscape and valleys.

Are there less crowded road bike trails near Windy Hill Open Space Preserve?

While popular routes can see more traffic, exploring some of the less-traveled roads or choosing to ride during off-peak hours (early mornings or weekdays) can offer a more serene experience. The preserve's extensive network means there are always options to find quieter sections.

Are there many loop road bike trails available in the preserve?

Yes, loop routes are a prominent feature of road cycling in Windy Hill Open Space Preserve. Many of the routes are designed as loops, allowing you to start and end at the same point. Examples include the Manzanita Way – Tree Tunnel on Portola Road loop and the Tree Tunnel on Portola Road – Lower Kings Mountain Road loop.

What do other road cyclists enjoy the most about road cycling in Windy Hill Open Space Preserve?

The area is highly rated by the komoot community, with an average score of 4.6 stars from over 230 reviews. Reviewers often praise the diverse terrain, from rolling hills to tree-lined sections, and the challenging climbs like Old La Honda Road, which offer rewarding views and a good workout.

How many road cycling routes are available in Windy Hill Open Space Preserve (Closed Areas)?

There are over 70 road cycling routes available for exploration in Windy Hill Open Space Preserve (Closed Areas), offering a wide range of options for different preferences and skill levels.

What kind of terrain can I expect on road cycling routes here?

Road cycling in Windy Hill Open Space Preserve is characterized by rolling hills, open vistas, and sections of forested roads. You'll encounter varied conditions, from gentle gradients suitable for leisurely rides to more challenging climbs that test your endurance.

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

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