Cupertino, California

Looking for the best cycling in Cupertino? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Cupertino. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Cycling Spots in and near Cupertino

  • Fremont, California

    Lake Elizabeth Loop

    3.0
    2.1 mi / 69 ft gain
    Lake Elizabeth is located in central Fremont.  It offers a nice break from the city streets and can be enjoyed by walkers, joggers, and bikers alike.  It is a park for all ages.   Other attractions include volleyball nets, multiple playgrounds, and aqua adventure park, geese, and peddle boats. ...
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  • Santa Cruz County, California

    Camp at Henry Cowell Redwoods Campground

    4.8
    / 665 ft gain
    Nestled in the Santa Cruz Mountains, Henry Cowell Redwoods State Park is a great weekend option for Bay Area residents. With approximately 30 miles of hiking trails, the incredible Garden of Eden swimming hole, and proximity to Santa Cruz - this campground is not to be missed! On sunny days, view...
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  • San Mateo County, California

    Run Sawyer Camp Trail

    5.0
    12 mi / 300 ft gain
    The Sawyer Camp Trail is a popular paved trail that stretches alongside the Crystal Springs Reservoir all the way to Hillcrest Blvd. The sixth mile crosses over the San Andreas Dam with nice views of San Andreas Lake.There are markers every half mile which makes timing and tracking your run easy....
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  • Capitola, California

    Camp at New Brighton Campground

    / 0 ft gain
    This Capitola camping spot is the place to be if you're looking to do a variety of activities in a variety of landscapes. You can swim, fish, or explore the nearby forest of Monterey Pine and coastal Oak. In the evening, walk into Capitola for live music and great fish tacos.  The S.S. Palo Alto,...
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  • San Francisco, California

    Bike the Golden Gate to Sausalito

    4.7
    Riding your bike across the Golden Gate Bridge to Sausalito, and then enjoying some drinks on the back deck at Sam's, is a great way to spend a nice day. The views along the way are simply breathtaking. After your ride and a day of fun in Sausalito, you can return to San Francisco by ferry. It's ...
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  • San Francisco, California

    Ride Paradise Loop

    4.3
    Riding this loop has long been a popular option for San Franciscan riders looking to escape the busy city streets. This 38-mile ride with 1,600 feet of elevation, is suitable for all personalities of rider: the fast paced racer or the person just out to relax and cruise.A great place to start thi...
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  • Mill Valley, California

    Headlands Ride to Point Bonita Lighthouse

    4.3
    The Headlands are a quick ride over the Golden Gate. On the ride, you'll see wildflowers, rugged coastline, and the Point Bonita Lighthouse. Once you cross the bridge, take Conzelman Rd up ~700 feet to Hawk Hill. From here, continue on to the lighthouse. On the return trip, head back on Conzelman...
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  • Pacific Grove, California

    Bike at Asilomar State Beach

    At Asilomar State Beach, adventure is accessible in many forms. I had the opportunity to rent a bike from Adventures by the Sea. Rentals start at $25, and while you are not permitted to ride along the boardwalk that leads you to the beach, you may walk your bike through the exquisite sand dunes A...
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  • Sand City, California

    Bikepack Highway 1: Monterey to San Luis Obispo

    130 mi / 9000 ft gain
    Please be aware that this is NOT a route for beginning cyclist. It is a very hilly route and you will be sharing the road with cars for the entire route, the shoulder is sometimes very slim. This should not scare you from doing the trip, just be aware of the risks and dangers you might be facing....
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