Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Road cycling routes
United States
California
Santa Clara County
Cupertino

Cupertino to Chesbro Reservoir County Park loop

Moderate

4.9

(8881)

8,882

riders

Cupertino to Chesbro Reservoir County Park loop

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:

Laguna Seca Conservation Area

Calero County Park

Lakeside Ranch Reserve

Waypoints

A

Start point

Parking

Get Directions

1

16.3 km

Shannon Road (climb)

Highlight (Segment) • Climb

From Los Gatos Creek Shannon Rd climbs initially gently to Blossom Hill Park, and then more steadily into the rural area up to the road summit below Blossom Hill

Tip by

2

34.5 km

Trailhead parking area with restrooms. Some sections of the Cottle Trail are nice packed gravel also suitable for regular or narrow tires.

Tip by

3

37.4 km

Calero Reservoir

Highlight • Lake

Great viepoint of this large reservoir created by a dam in the south of San Jose, open to boating.

Tip by

4

48.5 km

View of Chesbro Reservoir

Highlight • Viewpoint

The main perk of the ride is the pretty views of two separate reservoir lakes. Here you can enjoy the view on Chesbro Reservoir.

Tip by

B

95.0 km

End point

Parking

Loading

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

Sign up to see more specific route details

Sign up for free

Elevation

Elevation

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

Highest point (230 m)

Lowest point (50 m)

Sign up to see more specific route details

Sign up for free

Weather

Powered by Foreca

Today

Sunday 12 July

29°C

16°C

0 %

Additional weather tips

Max wind speed: 10.0 km/h

to get more detailed weather forecasts along your route

Comments

guide_signup

Want to know more?

Sign up for a free komoot account to join the conversation.

Sign up for free

This route was planned by komoot.

Save

Edit route

Download GPX

Move start point

Print

Share

Embed on a website

Report an Issue

Report restricted access

Frequently Asked Questions

What is the overall difficulty and terrain like for this cycling route?

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.

What are the main points of interest along the way?

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.

Where can I park to start this loop?

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.

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

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.

Is the Cupertino to Chesbro Reservoir County Park loop suitable for dogs?

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.

What is the best time of year to cycle this route?

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.

Are there any facilities like restrooms or water stops along the way?

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.

Does this route connect with other trails?

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.

What kind of scenery can I expect on this ride?

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.

How long does it typically take to complete this cycling loop?

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.

Is the route suitable for families with children?

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.

Nearby routes

Hard

5.0

468

Mount Hamilton & JD Grant Park loop from Berryessa

05:43h

77.6km

1,830m

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy