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Routes
Road cycling routes
United States
California
San Mateo County

North Fair Oaks

The best road cycling routes around North Fair Oaks

4.7

(219)

11,964

riders

204

rides

Road cycling routes around North Fair Oaks, an unincorporated area in San Mateo County, California, offer varied terrain for cyclists. The region features a distinct microclimate and is traversed by the Hetch Hetchy Aqueduct. Cyclists can find routes ranging from challenging climbs in coastal mountain woodlands to more relaxed rides along bayside recreational areas. The landscape includes rolling hills and tree-covered roads, providing diverse experiences for road cyclists.

Best road cycling routes around North Fair Oaks

  • The most popular road…

Last updated: May 13, 2026

5.0

(1)

18

riders

#1.

Half Moon Bay loop from Redwood City via Purisima Creek Road

77.9km

04:49

1,320m

1,320m

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

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Hard

4

riders

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

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

Moderate

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

Moderate

5.0

(2)

402

riders

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

Hard
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Tips from the Community

David B. Davis
August 31, 2025, Pulgas Water Temple

A fun, pretty place to stop while riding Cañada road. I has water and an air pump and bathrooms. Take a photo with friends.

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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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San Andreas Lake is a hidden gem tucked into the hills of San Mateo County, just south of San Francisco. Originally a natural sag pond formed by the San Andreas Fault, it was transformed into a reservoir in the late 1800s and now serves as a vital water source for the region. The lake is off-limits for swimming or boating, but you can enjoy its peaceful beauty from the San Andreas Trail or the popular Sawyer Camp Trail, which runs along its eastern edge. It's a serene spot where you can walk or bike with sweeping views of the water and surrounding hills, all while standing right on one of the world’s most famous fault lines. Despite its proximity to urban life, San Andreas Lake offers a quiet, scenic escape steeped in natural and historical significance.

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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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You're not hallucinating: This monument was deliberately built in the style of ancient Greek and Roman architecture, to commemorate the Great Depression-era Hetchy Hetchy Project that brought water down from the mountains to the Bay Area. The frieze says, “I give waters in the wilderness and rivers in the desert, to give drink to my people.”

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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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Andrus
February 19, 2025, Half Moon Bay

The tree lined streets of Hal Moon Bay invite you to explore its rich history, parks, eateries, art galleries. and more. While the area is mostly known for its beaches, be sure to allow yourself enough time to explore the town as well.

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The stretch of El Camino Real through downtown Milbrae is an area of focus for repurposing some of the 6 lanes for more cycle, pedestrian, and business traffic. The goal is to make a safer, friendly slow traffic zone for residents and visitors alike.

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Frequently Asked Questions

How many road cycling routes are available around North Fair Oaks?

North Fair Oaks offers a wide selection of road cycling routes, with nearly 200 different tours available. These routes cater to various skill levels, including over 70 easy rides, nearly 90 moderate options, and close to 40 challenging routes for experienced cyclists.

What kind of terrain can I expect when road cycling in North Fair Oaks?

The region around North Fair Oaks provides diverse terrain for road cyclists. You'll find everything from challenging climbs in coastal mountain woodlands, such as the popular Old La Honda Road – Tree Tunnel on Portola Road loop from Menlo Park, to more relaxed rides along bayside recreational areas. The landscape includes rolling hills and tree-covered roads, with some routes offering views of the Hetch Hetchy Aqueduct and Crystal Springs Reservoir.

Are there challenging climbs for experienced road cyclists in North Fair Oaks?

Yes, North Fair Oaks is known for its challenging climbs. For instance, Old La Honda Road is a popular ascent, nearly three miles long with an average grade just under 8%. Another demanding option is the Half Moon Bay loop from Redwood City via Purisima Creek Road, which is a difficult 48.4-mile route featuring significant elevation gain through coastal mountain terrain.

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

Many road cycling routes in the area offer scenic views and pass by notable natural features. You might encounter the Hetch Hetchy Aqueduct, views of the Crystal Springs Reservoir, or ride through tree-covered roads. For specific landmarks, consider visiting the Pulgas Water Temple or the Giant Eucalyptus Trees at Francisquito Creek Crossing. The broader San Mateo County also features diverse natural settings, including coastal marine reserves and mountain woodlands.

Are there any family-friendly road cycling routes in North Fair Oaks?

While many routes involve significant elevation, you can find more relaxed options. Junipero Serra Boulevard, for example, offers a generous, paved bike lane largely separate from car traffic, providing a rolling, straight run. For a moderate experience, the Crystal Springs Regional Trail Loop is a 30.9-mile path with a mix of rolling terrain and scenic views, suitable for families looking for a longer ride.

What do other cyclists say about road cycling in North Fair Oaks?

The road cycling routes around North Fair Oaks are highly regarded by the komoot community, with an average rating of 4.6 stars from over 200 reviews. More than 11,000 road cyclists have explored the area using komoot, often praising the varied terrain, from challenging climbs to scenic, tree-covered roads.

Are there any loop road cycling routes available?

Yes, many road cycling routes in North Fair Oaks are designed as loops, offering a convenient way to start and end your ride in the same location. Examples include the Old La Honda Road – Tree Tunnel on Portola Road loop from Menlo Park and the Crystal Springs Regional Trail Loop.

Where can I find parking for road cycling routes in North Fair Oaks?

Parking availability varies by route. Many routes start from nearby towns like Redwood City or Menlo Park, where public parking options may be available. For specific routes, it's advisable to check the individual tour details on komoot for recommended starting points and parking information.

What is the best time of year to go road cycling in North Fair Oaks?

North Fair Oaks benefits from a distinct microclimate, making it suitable for road cycling for much of the year. Spring is particularly vibrant, with wildflowers blooming in nearby areas like Edgewood Park and Natural Preserve. Generally, the mild California weather allows for enjoyable rides outside of extreme summer heat or heavy winter rains.

Are there any routes that offer a mix of climbing and exhilarating descents?

Absolutely. The region is known for its varied topography. While Old La Honda Road offers a significant climb, Kings Mountain Road provides an exhilarating descent, stretching over four miles with an average grade of approximately -7.5%, featuring a narrow, winding path under moderate tree cover. For a longer, challenging ride that combines both, consider the Lower Kings Mountain Road – Portola Valley loop from Redwood City.

Can I find routes that pass by lakes or water features?

Yes, several routes offer views of water features. The Crystal Springs Regional Trail Loop provides scenic views of the Crystal Springs Reservoir. Additionally, you might encounter highlights like Oracle Lagoon or the Duck Pond 🦆 Palo Alto wetlands on some routes or nearby.

Are there any easy road cycling routes for beginners?

Yes, North Fair Oaks has over 70 routes classified as easy, making them suitable for beginners or those looking for a more relaxed ride. These routes typically feature less elevation gain and shorter distances, allowing for a comfortable introduction to road cycling in the area.

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