Cupertino to Half Moon Bay loop
Cupertino to Half Moon Bay loop
2.6
(17)
51
riders
04:34
104km
980m
Road cycling
This difficult 64.6-mile road cycling loop from Cupertino to Half Moon Bay offers diverse scenery and challenging climbs.
Last updated: February 26, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Get Directions
19.0 km
Highlight • Rest Area
Tip by
39.6 km
Highlight (Segment) • Cycleway
Tip by
49.4 km
Highlight • Natural
Tip by
52.5 km
Highlight • Beach
Tip by
66.5 km
Highlight (Segment) • Viewpoint
Tip by
78.3 km
Highlight (Segment) • Cycleway
Tip by
86.0 km
Highlight (Segment) • Cycleway
Tip by
104 km
End point
Way Types & Surfaces
Way Types
50.1 km
49.9 km
3.86 km
< 100 m
< 100 m
< 100 m
Surfaces
103 km
657 m
109 m
< 100 m
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Elevation
Highest point (260 m)
Lowest point (0 m)
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Weather
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Wednesday 8 July
23°C
13°C
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This route was planned by komoot.
While the route starts in Cupertino, specific parking details aren't provided. Many cyclists park at local parks or public lots in Cupertino, ensuring they check any parking restrictions or fees. Consider starting near a park like El Camino Park in Palo Alto, which is along the route, for potential parking options.
This challenging racebike loop is approximately 104 kilometers (64.6 miles) long with significant elevation gain. It typically takes around 4 hours and 35 minutes of active cycling time, but plan for longer to account for breaks, scenic stops, and the demanding nature of the ride.
No, this loop is classified as a "difficult" road ride requiring "very good fitness." It features substantial elevation gain (around 975 meters or 3,200 feet) and prolonged ascents, particularly through the Santa Cruz Mountains foothills. It is not recommended for beginners.
The terrain is predominantly well-paved and suitable for road bikes. However, be prepared for some segments near Half Moon Bay, such as parts of Purisima Creek Road, that might involve gravel or unpaved sections. When the route uses Highway 1, you can generally expect a wide, paved shoulder and smooth pavement. The ride includes significant climbs into the Santa Cruz Mountains.
The route offers diverse and picturesque scenery. You'll experience mountain valleys and meadows inland, transitioning to dramatic coastal bluffs, secluded beaches, and sweeping Pacific Ocean views as you approach Half Moon Bay. Notable sights include riding beneath redwoods on the climb up Purisima Creek Road and views of Crystal Springs Reservoir from Cañada Road. You'll also pass highlights like Half Moon Bay Road and Francis Beach.
The best time to cycle this loop is generally during the spring and fall when temperatures are milder and coastal fog is less prevalent. Summer can be warm inland, and winter may bring rain and cooler temperatures, especially at higher elevations and along the coast. Always check weather conditions before you go.
No, there are no specific permits or entrance fees required to cycle the Cupertino to Half Moon Bay loop. It primarily uses public roads and designated cycle ways.
As a challenging road cycling route, this loop is not typically considered dog-friendly in the same way a hiking trail might be. Dogs are generally not suitable companions for a long, strenuous road bike ride of this nature.
Yes, the route intersects with several other paths. You'll find sections that utilize parts of the El Camino Real, Foothill Expressway, San Mateo North South Bicycle Route, and the Crystal Springs Trail. It also briefly touches the Pacific Coast Bike Route.
Yes, you'll pass through several towns and areas where you can find food and coffee. Half Moon Bay offers numerous options, and you might find smaller stops in towns along the way. The Pilarcitos Creek meadows & farm stand is a notable spot near Half Moon Bay.
Given the length and difficulty, you should bring plenty of water, energy snacks, and appropriate cycling gear. A repair kit, spare tube, and pump are essential. Dress in layers to adapt to changing temperatures, especially between the inland and coastal sections. Don't forget sunscreen and a helmet.
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