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Cupertino, California

Looking for the best hiking 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 Hiking Spots in and near Cupertino

  • 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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  • Half Moon Bay, California

    Purisima Creek Trail and Craig Britton Trail Loop

    4.0
    6.95 mi / 1411 ft gain
    This hike is perfect for any time of year, always staying cool because it is near the coast, and there are multiple creeks that flow year-round. Even on foggy days, the fog condenses on trees to make it seem like it is "raining." Be warned that this hike has a lot of elevation change and is stre...
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  • Half Moon Bay, California

    Stroll along the Southern Beaches at San Gregorio State Beach

    4.0
    2.9 mi / 413 ft gain
    Not a trail per se, but approximately 3 miles (down and back) of beautiful beach to walk down. Lots of interesting caves, wild animals, and rock formations to discover. This is a popular location for sea kayakers. San Gregorio State Beach was originally founded to protect the estuary at the back ...
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  • Morgan Hill, California

    Uvas Canyon Waterfall Hike

    4.0
    1.5 mi
    Uvas Canyon offers up to 6-miles of hiking trails, which includes a 1.5 mile loop, which runs along Swanson Creek and passes many of the park's waterfalls. To take short loop, head North out of the parking lot to the Swanson Creek Trail. Once you find Swanson Creek Trail, you'll be on the Waterfa...
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  • Davenport, California

    Hike around Greyhound Beach and Climb Greyhound Rock

    0.7 mi / 0 ft gain
    The trailhead is at the Greyhound Rock State Marine Conservation Area which is directly off Highway 1. There is a large paved parking lot with a good amount of trees so finding a shady parking spot isn't that difficult (if that's important to you). The parking lot is located on the beach cliffs ...
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  • Belmont, California

    Hike San Mateo's Sugarloaf Mountain

    5.0
    1.5 mi / 500 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 bo...
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  • Santa Cruz, California

    Hike the Rincon Fire Trail

    5.0
    1 mi / 300 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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  • Soquel, California

    Land of Medicine Buddha Loop

    4.5
    5.74 mi / 915 ft gain
    Near the retreat, there is a short trail called "Eight Verses Pilgrimage Trail" providing people with the opportunity to meditate on thought transformation in a peaceful and picturesque outdoor setting. From there, a beautiful 6 mile loop will take you up to the top of the ridge and then back aro...
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  • Half Moon Bay, California

    Hike the Cowell-Purisma Trail

    5.0
    7 mi / 400 ft gain
    This is a popular trail that has beach access to Cowell Ranch Beach.  Along the trail, there is a steep staircase that goes down to the beach.  The trail also features fields, a bridge, and beautiful views of California's rugged coastline.  This trail is paved in some parts, and can also be biked...
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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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  • Aptos, California

    Hike to Nisene Marks' Maple Falls

    4.6
    8.5 mi / 900 ft gain
    As you enter the park, you'll need to pay $8 for parking via a self-pay envelope, so it's recommended that you bring exact change. At the park booth, be sure to grab a map. The hike can be a little tricky with no cell service and limited trail signage. Once you've grabbed your map, keep driving p...
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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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  • Pleasanton, California

    Courdet Trail and Schuhart Trail

    5.24 mi / 1122 ft gain
    This is a 5+ mile out and back trail through the hills in the South Bay. The beginning of the hike has a steeper incline and then becomes more gradual later on. There is a beautiful views of the South Bay that are enjoyable in the day, but are fantastic in the evening. Some areas of the trail hav...
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  • Capitola, California

    New Brighton Beach Trail

    0.85 mi / 112 ft gain
    New Brighton Beach Trail is an out-and-back trail that takes you past scenic surroundings located near Aptos, California.
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  • Half Moon Bay, California

    Hike Along the Half Moon Bay Coastal Trail

    4.6
    5 mi / 104 ft gain
    Start at the visitor center along Kelly Avenue. Take note that the day parking fee is $10 in 2016 for each vehicle. You will then be able to enjoy both the Coastside Trail and Francis Beach (plus other beaches) with access to the amenities such as coin-operated showers and a semi-private beach.Th...
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