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United States
California
San Mateo County

Windy Hill Open Space Preserve

The best cycling routes in Windy Hill Open Space Preserve

4.8

(77)

2,157

riders

50

rides

Touring cycling in Windy Hill Open Space Preserve offers routes through a landscape characterized by rolling hills and open grasslands, providing expansive views of the surrounding area. The preserve features varied terrain, including paved roads and dedicated bike trails, with elevations that present moderate climbs. These routes often connect to nearby historic sites and natural areas, making for diverse cycling experiences.

Best touring cycling routes in Windy Hill Open Space Preserve

  • The most popular touring cycling route is Portola Roadโ€ฆ

Last updated: May 13, 2026

25

riders

#1.

Old La Honda Road โ€“ Tree Tunnel on Portola Road loop from Portola Valley

22.1km

01:36

490m

490m

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

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Hard

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

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

Hard

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

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Andrus

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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Aliseโ€™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 vibeโ€”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, itโ€™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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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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Alameda de las Pulgas Road has consistent traffic but features a good bike lane for safe cycling. The route is straightforward and flat, it works for a smooth ride through the area.

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maniboyflex
January 18, 2025, Gerona Road Tree

Gerona Road area is quiet and residential; it is also flat, well-paved and surrounded by some cool trees. Perfect for an easy ride.

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Frequently Asked Questions

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

Windy Hill Open Space Preserve offers nearly 40 touring cycling routes. These routes vary in difficulty, with 7 easy, 19 moderate, and 12 difficult options, providing diverse experiences for cyclists.

Are there beginner-friendly touring cycling routes in Windy Hill Open Space Preserve?

Yes, there are several routes suitable for beginners. The preserve features 7 easy touring cycling routes, which are generally shorter and have less elevation gain, making them ideal for those new to touring cycling or looking for a relaxed ride.

Are there circular touring cycling routes available in Windy Hill Open Space Preserve?

Many of the touring cycling routes in Windy Hill Open Space Preserve are designed as loops, allowing you to start and end at the same point. For example, the Portola Road โ€“ Woodside Store (Historic Site) loop from Enid Pearson-Arastradero Preserve is a popular circular option.

Where can I find parking for touring cycling routes in Windy Hill Open Space Preserve?

Common starting points for many routes, such as the Enid Pearson-Arastradero Preserve, typically offer parking facilities. It's advisable to check specific route details on komoot for recommended parking areas near your chosen starting point.

What scenic viewpoints or attractions can I expect to see along the touring cycling routes?

Along the touring cycling routes, you can enjoy expansive views of the surrounding area, including the Windy Hill Open Space Preserve Scenic View. Other notable attractions include the historic Woodside Store, which is passed by on the Portola Road โ€“ Woodside Store (Historic Site) loop, and the Windy Hill Summit itself, offering panoramic vistas.

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

The preserve is enjoyable year-round, but spring and fall offer the most pleasant conditions with mild temperatures and lush landscapes. Summers can be warm, especially in open areas, while winters are generally mild but may bring occasional rain.

Are dogs allowed on the touring cycling routes in Windy Hill Open Space Preserve?

Dogs are generally permitted on leash on designated trails within Windy Hill Open Space Preserve. However, specific regulations can vary, so it's always best to check the official Midpeninsula Regional Open Space District website for the most current rules regarding pets on trails.

Are the touring cycling routes in Windy Hill Open Space Preserve suitable for families?

Many of the moderate and easy routes are suitable for families, especially those with some cycling experience. The varied terrain and dedicated bike paths, such as those found on the Rossotti's Alpine Inn โ€“ Los Altos-Palo Alto Bike Trail loop, offer enjoyable rides for different skill levels.

What kind of wildlife might I encounter while cycling in Windy Hill Open Space Preserve?

Windy Hill Open Space Preserve is home to diverse wildlife. Cyclists might spot deer, various bird species including raptors, and smaller mammals. Keep an eye out, especially during dawn and dusk, for opportunities to observe local fauna.

What are the typical cycling conditions in Windy Hill Open Space Preserve, and what should I wear?

The preserve features varied terrain, from paved roads to dedicated bike trails, with rolling hills and moderate climbs. Conditions can change, so layers are recommended. Wear appropriate cycling attire, bring sun protection, and carry enough water, especially on longer routes or warmer days.

Are there cafes or places to refuel near the touring cycling routes?

While the preserve itself is natural open space, the surrounding towns like Portola Valley and Woodside offer various cafes and eateries where you can refuel before or after your ride. Some routes, like the Dwight Crowder Path โ€“ Rossotti's Alpine Inn loop, pass by establishments like Rossotti's Alpine Inn.

How does touring cycling in Windy Hill Open Space Preserve compare to nearby areas like Huddart Park?

Windy Hill Open Space Preserve is known for its expansive open grasslands, rolling hills, and panoramic views, often featuring more exposed terrain. Huddart Park, by contrast, is typically more forested with shadier trails. Both offer varied cycling experiences, but Windy Hill provides a distinct open-space feel.

What do other touring cyclists enjoy the most about touring cycling 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 60 reviews. Reviewers often praise the stunning panoramic views, the well-maintained trails, and the challenging yet rewarding climbs that offer a great workout amidst beautiful scenery.

Most popular routes in Windy Hill Open Space Preserve

Hiking in Windy Hill Open Space Preserve

Most popular attractions in Windy Hill Open Space Preserve

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