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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

  • La Honda, California

    Hike through Portola Redwoods State Park

    4.8
    7 mi
    Like redwood hikes? We do too, they're always very scenic and take you away from the hustle and bustle of the bay area. Not to mention, they also stay cool during the summer months. If you want a hike in the middle of the peninsula, this is a great bet.When starting this hike, head out from headq...
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  • La Honda, California

    Hike the Brook Trail Loop

    7.1 mi / 1500 ft gain
    The Brook Trail Loop is a beautiful hike, starting off in Sam McDonald County Park and later entering into Pescadero Creek County Park. This adventure can be done in any season, with the trails almost entirely shaded for even the hottest summer days. Starting off from the Heritage Grove trailhead...
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  • Portola Valley, California

    Sunrise Hike at Windy Hill

    5.0
    There are a few options to this hike. Usually I would recommend parking in the lot on Portola Road, but because the preserve doesn't open until 30 minutes before sunrise, it's best to park up on Skyline Boulevard (Highway 35). There are two places to park up on Skyline, but the main parking lot i...
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  • La Honda, California

    Sam McDonald Park Loop

    5.0
    12.19 mi / 2192 ft gain
    The Pescadero Creek Park Complex is a great place to escape for a day or overnight hike in the heart of the Bay Area. You will need to get a permit to stay overnight - these can be attained on a first-come, first-serve basis from the ranger station. Most of the campsites here are also available f...
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  • San Jose, California

    North Rim Trail to Eagle Rock

    5.0
    1.94 mi / 240 ft gain
    North Rim Trail to Eagle Rock is an out-and-back trail that takes you past scenic surroundings located near San Jose, California.
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  • Woodside, California

    Hike through Wunderlich County Park

    5.0
    4.5 mi / 1400 ft gain
    Located in the iconic Silicon Valley town of Woodside, Wunderlich County Park offers a number of hiking trails as well as some horseback riding trails through the wilderness.  Once in the parking lot, you will see a number of stables, riding ring, as well as a beautiful historic stable that was o...
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  • Fremont, California

    Mission Peak via Hidden Valley Trail

    4.2
    6.16 mi / 2116 ft gain
    Breathtaking views of the Bay Area are your reward for making this climb to the top of Mission Peak. It’s a 3-mile trek to the top of the peak and then back down the same way. This is a moderate hike that provides a nice workout – so be prepared. Park at the Stanford Avenue entrance gate. There ...
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  • Loma Mar, California

    Bike Pescadero Creek County Park

    5.0
    12.5 mi / 1350 ft gain
    Pescadero Creek County Park and the connected Sam McDonald and Memorial Park are located deep in the Santa Cruz Mountains holding a vast network of secluded trails. From biking to backpacking, this area is a perfect place for a day or weekend adventure. This area also has the added bonus having r...
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  • San Jose, California

    Explore Santa Teresa County Park

    4.5
    8.3 mi / 2053 ft gain
    The Santa Teresa County Park loop is perfect for wildlife viewing! Be ready to see deer, coyote, hawks, turkeys, pigs and cows. The trail is rated as moderate - be cautious with mud if you are visiting the park after a rain shower. Dogs are allowed in the park, but must be kept on leash.  There i...
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  • Loma Mar, California

    Camp Under the Redwoods at Memorial Park

    With old growth redwoods and a creek swimming area, Memorial Park is a perfect escape from the hustle and bustle of the Bay Area. Memorial Park is only a few miles east of the town of Pescadero. To get here, you can either approach from Highway 1 and drive up Pescadero Creek Road or take Highway ...
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  • Boulder Creek, California

    Hike the Berry Creek Falls Loop

    4.8
    11 mi / 2000 ft gain
    Nestled in California's oldest state park, the popular Berry Creek Falls Loop hike begins at the Big Basin park headquarters. If you're up for 11 miles, a thousand feet of elevation gain through towering redwoods and along serene creeks, and spread out over a half-day, then this is the hike for y...
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  • Boulder Creek, California

    Camp at Big Basin Redwoods State Park

    4.0
    0.5 mi
    Big Basin is currently closed including the campgrounds. Please visit the Parks.ca.gov site for updated details.  An hour away from the thrumming city of San Jose, ancient immense trees live in a forest full of vibrant ferns and rushing waterfalls. Big Basin Redwoods State Park encompasses 10,00...
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  • Boulder Creek, California

    Hike the Ocean View Summit Loop

    4.0
    6 mi / 600 ft gain
    This hike begins at the Big Basin park headquarters. If you're up for 6 miles through giant redwoods and along serene creeks, and with an ocean view, then this is the hike for you. Ocean view summit loop starts on the Gazos Creek Road bridge, next turn right on to the Middle Ridge Fire Road, whic...
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  • Boulder Creek, California

    Hike the Old Growth Redwoods Trail

    4.5
    0.5 mi
    Quick half-mile stroll through the old growth Redwoods that will show you the nature of the ever-living redwood tree.Redwoods are capable of withstanding storms, floods, fire, droughts, and even termites. These legendary trees can live for over 2,000 years and possess incredible strength, vigor, ...
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  • Boulder Creek, California

    Big Basin's Sunset Trail Camp

    4.8
    9.46 mi / 2146 ft gain
    This trail and campsite is currently closed (learn more). Looking for a more authentic hiking and camping weekend, without having to drive hours away to find it? Then the Sunset Trail Camp within Big Basin Redwoods SP is your ticket. To access this site, you'll need to hike the famous Skyline-to...
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  • Boulder Creek, California

    Hike to Sempervirens Falls

    4.0
    2.1 mi / 100 ft gain
    The hike to Sempervirens Falls is an easy 2.1 mile out-and-back hike on the Sequoia Trail. You'll travel through the redwood forest and some of the campgrounds located in Big Basin State Park. The hike is pleasant but on occasion, you'll be too close to the road to feel like you're deep in the wi...
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