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Routes
Road cycling routes
United States
California
Santa Clara County
Cupertino

Cupertino to Half Moon Bay loop

Hard

2.6

(17)

51

riders

Cupertino to Half Moon Bay loop

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:

Edgewood Park and Nature Preserve

Half Moon Bay State Beach

Waypoints

A

Start point

Get Directions

1

19.0 km

El Camino Park Palo Alto

Highlight • Rest Area

El Camino Park in central Palo Alto is a newly renovated sports facility. There is a synthetic soccer field, lighted softball diamond, toilets and parking.

The park was established in 1914 and is leased from Stanford University.

Tip by

2

39.6 km

Half Moon Bay Road

Highlight (Segment) • Cycleway

Scenic road across the peninsula, best taken downhill from Skyline as it has no shoulder and can get busy; so it's safer to take the full lane at downhill speeds.

Tip by

3

49.4 km

Open meadows and farmland in the creek valley, with a great fresh farm stand, often with local bee honey for sale. In fall there's a big pumpkin patch.

Tip by

4

52.5 km

Francis Beach

Highlight • Beach

Part of the dozens of miles long beaches along Half Moon Bay. Campground, picnic area, restrooms, water.

Tip by

5

66.5 km

Bike Sunday - no motorized vehicles on Sundays, we've got the whole road for ourselves.

Tip by

6

78.3 km

Cañada Road & Woodside Road

Highlight (Segment) • Cycleway

Sundays Cañada Road is closed to cars, biker-heaven toward Crystal Springs bike path.

Tip by

7

86.0 km

Junipero Serra Boulevard

Highlight (Segment) • Cycleway

Junipero Serra Boulevard has a generous, paved bike lane in both directions for the entire length of the ride.
Car traffic is everpresent on this route, and it can get …

Tip by

B

104 km

End point

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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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Frequently Asked Questions

Where can I park to start the Cupertino to Half Moon Bay loop?

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.

How long does it typically take to complete the Cupertino to Half Moon Bay loop?

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.

Is the Cupertino to Half Moon Bay loop suitable for beginners?

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.

What is the terrain like on the Cupertino to Half Moon Bay loop?

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.

What kind of scenery can I expect along the route?

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.

What is the best time of year to cycle the Cupertino to Half Moon Bay loop?

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.

Do I need any permits or pay entrance fees for this cycling route?

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.

Is the Cupertino to Half Moon Bay loop dog-friendly?

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.

Does the route intersect with other well-known cycling paths?

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.

Are there places to stop for food or coffee along the 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.

What should I bring for this challenging ride?

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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