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Routes
Road cycling routes
United States
California
San Mateo County

Windy Hill Open Space Preserve

The best traffic-free bike rides in Windy Hill Open Space Preserve

4.7

(109)

5,972

riders

7

rides

Road cycling in Windy Hill Open Space Preserve is characterized by its breezy, grass-covered hilltop, which reaches an elevation of 1,905 feet. This distinctive ridge offers panoramic views across the San Francisco Bay, the Pacific Ocean, and the Santa Clara Valley. The preserve encompasses diverse ecosystems, including open grasslands and sheltered forests of redwood, fir, and oak. While internal trails have limited access for road cycling, the surrounding public roads provide numerous challenging and scenic no traffic road cycling routes.

Last updated: May 14, 2026

12

riders

#1.

Rossotti's Alpine Inn – Dwight Crowder Path loop from Los Trancos Open Space Preserve

24.0km

01:26

470m

470m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult 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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5.0

(2)

84

riders

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

Moderate

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

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

Bay Area Ridge Trail — Hiking the backbone of The Bay

Traffic-free bike rides in Windy Hill Open Space Preserve

Traffic-free bike rides in Windy Hill Open Space Preserve

Other adventures in Windy Hill Open Space Preserve

Bay Area Ridge Trail — Hiking the backbone of The Bay

Hiking Collection by

Andrus

Tips from the Community

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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The Rodin Sculpture Garden at Stanford’s Cantor Center for the Arts offers a peaceful, art-filled detour for runners exploring campus. Located just off Palm Drive, the garden features one of the largest collections of Auguste Rodin’s bronze works outside Paris—including The Thinker and The Gates of Hell. Wide, paved paths wind through the outdoor space, making it easy to jog through or pause for a contemplative break. It’s a favorite spot for morning and evening runners, offering shade, quiet, and inspiring surroundings. The garden is open year-round and sits near several scenic campus running loops and trail connectors.

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This mostly paved bike trail alongside Alpine Road is great for bike commuting — 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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Page Mill Road is a classic route for cyclists looking for a challenge, with its steep climbs, sharp switchbacks, and stunning views of Silicon Valley. Starting near Palo Alto and climbing into the Santa Cruz Mountains, the ride tests your legs but rewards you with breathtaking scenery. Be prepared for varying gradients, especially in the lower sections, and pack plenty of water—the climb can be intense, especially on warmer days.

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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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The Cantor Arts Center is one of the premier art museums in the area. The museum hosts a rotation of permanent and temporary exhibitions and has been open since 1894.

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

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Frequently Asked Questions

How many no-traffic road cycling routes are available in Windy Hill Open Space Preserve?

There are over 10 curated no-traffic road cycling routes available in and around Windy Hill Open Space Preserve. These routes are designed to offer a serene cycling experience away from heavy vehicle traffic.

What is the general difficulty level of road cycling routes in Windy Hill Open Space Preserve?

The road cycling routes in this area cater to a range of abilities. You'll find a good mix, with approximately 4 easy routes, 8 moderate routes, and 1 more challenging route, ensuring options for various fitness levels.

What kind of views can I expect on these no-traffic road cycling routes?

The routes in and around Windy Hill Open Space Preserve are renowned for their breathtaking panoramic views. You can expect to see expansive vistas stretching across the San Francisco Bay, the Pacific Ocean, the Santa Clara Valley, and even Stanford University. On clear days, you might even spot Mount Tamalpais and Mount Diablo. The preserve itself is characterized by its breezy, grass-covered hilltop, offering unobstructed scenery.

Are there any loop road cycling routes in the area?

Yes, several excellent loop routes are available. For example, the Alpine Road loop from Jasper Ridge Biological Preserve offers a moderate ride covering about 16.7 km. Another popular option is the Old La Honda Road loop from Stanford Linear Accelerator Center National Accelerator Laboratory, which is a longer, more challenging loop at around 28.6 km.

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

The komoot community highly rates the road cycling experience in this area, with an average score of 4.64 out of 5 stars from over 140 reviews. Cyclists frequently praise the stunning panoramic views, the challenging yet rewarding climbs, and the opportunity to ride on scenic roads like Old La Honda Road and Skyline Boulevard with minimal traffic.

Are there any specific landmarks or points of interest I can see along these routes?

Absolutely! Many routes offer views of notable landmarks. You might pass through Portola Valley, or catch glimpses of the Windy Hill Summit. The Windy Hill Open Space Preserve Scenic View is a highlight for many, offering those expansive vistas the area is famous for.

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

While the region offers good cycling conditions year-round, spring is particularly beautiful when the preserve's meadows burst into bloom with wildflowers. The breezy nature of Windy Hill means it can be cooler at higher elevations, so checking weather conditions is always recommended, especially for wind.

Are there any family-friendly no-traffic road cycling routes?

While many routes involve significant elevation gains, some of the easier routes might be suitable for families with older, more experienced children. It's best to review the specific route details, including distance and elevation, to determine suitability for your family's skill level. The focus on 'no traffic' roads certainly enhances safety for family rides.

What are some of the longer, more challenging no-traffic road cycling routes?

For those seeking a greater challenge, routes like the Old La Honda Road loop from Stanford Linear Accelerator Center National Accelerator Laboratory stand out. This moderate-to-difficult route covers approximately 28.6 km with significant elevation gain, offering a rewarding experience for advanced cyclists.

Can I find routes that incorporate popular cycling roads like Old La Honda Road or Alpine Road?

Yes, the surrounding public roads are a significant draw for road cyclists, and many komoot routes incorporate these iconic stretches. You'll find routes that utilize Old La Honda Road, Skyline Boulevard (Highway 35), Portola Road, and Alpine Road, all known for their scenic beauty and challenging climbs, often with less traffic than major thoroughfares.

Are there any routes that pass by natural features like ponds or forests?

While the primary focus of these road cycling routes is the open roads and panoramic views, the preserve itself encompasses diverse ecosystems. These include sheltered forests of redwood, fir, and oak, as well as lush sections with California bay and madrone. The region research mentions Sausal Pond, a marshy pond known for wildlife, though direct road cycling access to it might be limited to surrounding roads.

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