Cupertino, California

Looking for the best running 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 Running Spots in and near Cupertino

  • Redwood City, California

    Crystal Springs Trail Loop

    4.0
    5.4 mi / 1227 ft gain
    This is a great hike for any season of the year, with rushing streams during the winter, wildflowers in the spring, and cool, shaded canyons during the summer. Starting from near the Zwierlein Picnic area, take the Crystal Springs to the left into the redwood forest. Stay straight at the next tr...
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  • Emerald Hills, California

    Sylvan Loop Trail

    2.53 mi / 522 ft gain
    Sylvan Loop Trail is a loop trail where you may see wildflowers located near Redwood City, California.
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  • Emerald Hills, California

    Edgewood Loop

    4.0
    3.29 mi / 607 ft gain
    Edgewood Park and Natural Preserve rests in San Mateo County, California. The sweeping hillsides exemplify the true native flora of California, as the foundation of rock and soil is poor in nutrients. Only a few specialized native plants are adapted to live here--don't miss the unique wildflower ...
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  • Sunol, California

    Little Yosemite via Ohlone Road

    5.0
    2.17 mi / 207 ft gain
    Little Yosemite via Ohlone Road is an out-and-back trail that is good for all skill levels located near Sunol, California. The trail follows Alamdeda Creek along a wide gravel road with hills offering up better views of the creek at times.  Keep in mind this trail is very exposed and can get hot...
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  • Redwood City, California

    Cordilleras & Dusty-Footed Woodrat Loop

    3.7
    3.83 mi / 676 ft gain
    Getting there: exit Highway 280 at Edgewood Road, travel .75 miles east, turn left on Crestview Drive, then immediately left again on Edmonds Road. Once parked, there are several different path options through the park. All of them connect in a large loop, and return to the parking lot. The Cord...
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  • Redwood City, California

    Hassler Loop Trail

    4.0
    1.48 mi / 289 ft gain
    Experience the natural beauty of the San Francisco Peninsula on the scenic Hassler Loop Trail, a 1.5-mile moderately challenging hiking trail nestled in Redwood City's Emerald Hills neighborhood. This beloved local trail offers hikers, nature enthusiasts, and outdoor adventurers a perfect blend...
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  • Redwood City, California

    Methuselah and El Corte De Madera Creek Loop

    6.5 mi / 1778 ft gain
    This loop hike will provide people with the opportunity to experience the tranquility of the lower canyons of the preserve, which tend to be more isolated than the heavier-trafficked trails that are closer to the main highway. Be warned that this hike is fairly strenuous because of the large amo...
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  • Scotts Valley, California

    Lodato Loop Trail

    5.0
    1.24 mi / 315 ft gain
    Lodato Loop Trail is a loop trail that is moderately difficult located near Scotts Valley, California.
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  • Pescadero, California

    Canyon Rim Route

    5.0
    8.94 mi / 2070 ft gain
    Located deep within the Santa Cruz Mountains, Butano State Park boasts a large redwood canyon with many miles of hiking trails as well as campsites. This state park is one of the quietest and least visited parks on the peninsula making a perfect place to escape the hustle of the Bay Area  Butano...
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  • Redwood City, California

    Whittemore Gulch and Harkins Ridge Loop Trail

    4.6
    6.43 mi / 1772 ft gain
    There are two places to park for this specific loop- the main parking area on Highway 35 (Skyline Boulevard) and a smaller parking lot on the western end of the park. I would recommend parking at whichever is closest. Find directions to both on Openspace.org. From the main parking lot, the trail...
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  • Redwood City, California

    Whittemore Gulch and Purisima Creek Loop Trail

    9.27 mi / 2165 ft gain
    The Whittemore Gulch and Purisima Creek Loop Trail, nestled in the scenic Purisima Creek Redwoods Open Space Preserve near Redwood City, California, is a popular choice for hikers looking for a moderately challenging yet rewarding experience. This 9-mile loop trail winds through lush redwood fo...
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  • Felton, California

    Redwood Grove Loop

    4.0
    0.93 mi / 144 ft gain
    Henry Cowell Redwoods State Park is located just a few miles north of the city of Santa Cruz, along Highway 9. The park is home to an array of hiking and biking trails, but the crown jewel of the park is the Redwood Grove Loop Trail, which is only a 1/4 mile in from the park's entrance. Many peo...
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  • San Mateo, California

    Sugarloaf Mountain

    5.0
    1.64 mi / 417 ft gain
    Sugarloaf is tucked away in Laurelwood Park which is located in a residential neighborhood right off of Hwy 92 in San Mateo, making this a great hiking & trail running option for Peninsula residents. I always park on Glendora Dr. and follow the paved path down towards the playground. At the ...
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  • Santa Cruz, California

    Rincon Fire Trail to San Lorenzo River

    5.0
    1.42 mi / 328 ft gain
    The Rincon Fire Trail Starts at a small dirt parking lot next to CA-9 and traverses down the mountain to the San Lorenzo River Connecting with the Pipeline Trail. The trail can be a simple one of a mile out and back or up to 5 miles depending on your preference. The elevation will change by about...
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  • Sunol, California

    Hike the Pleasanton Ridge Trail

    4.3
    6.4 mi / 1443 ft gain
    Pleasanton Ridge Trail is a 6.4 mile loop. The loop is shared by dog walkers, trail runners, hikers, mountain bikers and horseback riders. From the ridge your viewpoints will include Mount Diablo and the San Francisco Bay.  This hike from the Foothills Staging Area is an excellent introduction ...
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  • San Mateo County, California

    Sawyer Camp Trail

    5.0
    11.61 mi / 1152 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 eas...
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