Cupertino to Chesbro Reservoir County Park loop
Cupertino to Chesbro Reservoir County Park loop
4.9
(8881)
8,882
riders
03:58
95.0km
610m
Road cycling
This road cycling loop from Cupertino to Chesbro Reservoir County Park offers a diverse ride through the Santa Cruz Mountains foothills, blending challenging climbs with serene natural beauty. You'll pedal past the expansive Calero Reservoir, then continue into a more rural setting, eventually reaching the peaceful Chesbro Reservoir, known for…
Last updated: June 9, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Parking
Get Directions
16.3 km
Highlight (Segment) • Climb
Tip by
34.5 km
Highlight • Trail
Tip by
37.4 km
Highlight • Lake
Tip by
48.5 km
Highlight • Viewpoint
Tip by
95.0 km
End point
Parking
Way Types & Surfaces
Way Types
52.9 km
37.6 km
4.40 km
105 m
< 100 m
Surfaces
93.3 km
1.71 km
105 m
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Elevation
Highest point (230 m)
Lowest point (50 m)
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Weather
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Today
Sunday 12 July
29°C
16°C
0 %
Additional weather tips
Max wind speed: 10.0 km/h
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This route was planned by komoot.
This is considered a moderate road ride, best suited for cyclists with good fitness. The route covers approximately 95 kilometers with an elevation gain of around 610 meters. You'll find mostly well-paved surfaces, but some segments will require effort due to the elevation changes as you ride through the foothills of the Santa Cruz Mountains.
The route offers picturesque views throughout. Key highlights include the challenging Shannon Road (climb), the scenic Cottle Trail - Rancho San Vicente Trailhead, and views of Calero Reservoir. The ride culminates with beautiful views of Chesbro Reservoir itself, set in a tranquil, rural landscape.
While the loop starts in Cupertino, specific parking details for the start are not provided. However, Chesbro Reservoir County Park, a key destination on the loop, offers parking at its entrances. The park is open from 8 a.m. until sunset.
No, there are no fees required at the entrances to Chesbro Reservoir County Park, and no specific permits are mentioned for cycling this route. You can enjoy the ride without worrying about additional costs or paperwork.
This route is primarily a road cycling loop. While Chesbro Reservoir County Park itself may have specific rules regarding dogs, the general nature of a long road cycling route means it's not typically considered 'dog-friendly' in the traditional sense for pets to run alongside. If you plan to bring a dog in a trailer, ensure it's safe and secure for the duration of the ride.
The park is open year-round, and the route can be enjoyed in most seasons. However, for optimal cycling conditions, consider spring and fall when temperatures are milder and the scenery is vibrant. Always check local weather forecasts before heading out, especially for potential heat in summer or rain in winter.
While the route passes through various areas, specific facilities like restrooms or water fountains are not detailed. It's always recommended to carry sufficient water and snacks for the entire 95-kilometer ride and plan any stops in towns like Morgan Hill for refreshments.
Yes, the route incorporates sections of several other paths. You'll find yourself on parts of the Campbell/Curtner/Tully Corridor, Almaden Expressway, Old Highway 9 Corridor, and Saratoga-Los Gatos, among others. These connections help form the extensive loop.
You'll experience diverse and scenic views, from the picturesque foothills of the Santa Cruz Mountains to tranquil backcountry landscapes. The highlight is undoubtedly the serene Chesbro Reservoir, and you might even catch views of other reservoirs like Calero, adding to the natural beauty of the ride.
The estimated duration for this 95-kilometer (59-mile) racebike loop is approximately 3 hours and 57 minutes. This is an average, and your actual time may vary based on your fitness level, speed, and any stops you make along the way.
Given its moderate difficulty, significant distance (95 km), and elevation gain (610 m), this loop is generally not recommended for young children or inexperienced family cyclists. It's better suited for adults or older, experienced teenagers with good fitness levels who are comfortable with longer road rides.
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