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.
Last updated: May 13, 2026
5.0
(1)
18
riders
77.9km
04:49
1,320m
1,320m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
49.7km
02:35
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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4.9
(9)
744
riders
69.6km
02:59
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.8
(9)
457
riders
50.6km
02:13
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
402
riders
98.5km
05:02
1,690m
1,690m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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