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

  • Burlingame, California

    Mills Canyon Nature Area Trail Loop

    4.0
    1.45 mi / 331 ft gain
    Nestled within Burlingame, California, the Mills Canyon Nature Area Trail Loop offers hikers a serene escape into nature. This approximately 1.5-mile loop meanders through diverse landscapes, including mixed woodlands and grasslands, providing opportunities for birdwatching and enjoying native ...
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  • Burlingame, California

    Ed Taylor Loop Trail

    4.0
    1.42 mi / 295 ft gain
    This hike can be done at any time of year. Hiking in winter and spring means that many varieties of wildflowers will be present, and the creek will have much more water. Summer and fall mean higher temperatures and drier conditions, but the hike is still a pleasant experience. Begin the hike at ...
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  • Castro Valley, California

    Lake Chabot Regional Park Loop

    4.3
    8.65 mi / 1263 ft gain
    Looking for a fun day on a lake, but don't want to drive too far? We recommend heading out to the East Bay where you can combine a nice hike with an afternoon of fishing. This moderately challenging hike remains scenic throughout the 8.5 mile trek around the lake, and offers many opportunities fo...
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  • Millbrae, California

    Sawyer Camp Trail: San Andreas Lake to Lower Crystal Springs Reservoir

    4.0
    5.35 mi / 354 ft gain
    Sawyer Camp Trail: San Andreas Lake to Lower Crystal Springs Reservoir is an out-and-back trail where you may see beautiful wildflowers located near Millbrae, California.
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  • Morgan Hill, California

    Mississippi Lake via Coe Headquarters

    5.0
    25.52 mi / 4974 ft gain
    If you're tired of trying and failing to get reservations for backcountry camping around the bay area, then Henry Coe State Park is the perfect place to visit. No reservations need to be made prior to the trip. All you need to do is get to the HQ on the morning of your trip, get your permits and ...
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  • Half Moon Bay, California

    Catch the Sunset at Maverick's Beach

    5.0
    1 mi
    Maverick's beach is most well-known for the Maverick surf competition and the gnarly waves which surface here in the winter months. For the rest of the year, the beach is still a site to see. With huge waves crashing ¼ mile off shore and bluffs towering 100 feet above you, it’s a picturesque plac...
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  • Moss Beach, California

    Pillar Point Bluff Loop

    4.7
    1.84 mi / 154 ft gain
    Sitting on a 140 acre bluff top, the Pillar Point Bluffs are a simple, easy hike with breathtaking views throughout. The bluffs are 22 miles from San Francisco – a 30 minute drive depending on the traffic. There is a small 10 car or so parking lot off of Airport Blvd, but there are two additional...
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  • San Bruno, California

    Live Oak to Buckeye and Quail Loop

    4.0
    1.03 mi / 148 ft gain
    Live Oak to Buckeye and Quail Loop is a loop trail that is good for all skill levels located near San Bruno, California.
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  • Moss Beach, California

    Cypress Tree Tunnels at Moss Beach

    4.5
    0.79 mi / 105 ft gain
    The Cypress Tree Tunnels are a quick jaunt from San Francisco (22 miles) and make for a great half-day trip. Getting here depends on traffic, but 30 minutes from the center of the city is doable. Parking is relatively easy. You can either park at the south end of the area at the Cypress Cove entr...
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  • Pacifica, California

    Brooks Falls Loop

    4.0
    2.26 mi / 781 ft gain
    Brooks Falls Loop is a loop trail that takes you by a waterfall located near Pacifica, California.
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  • Moss Beach, California

    Fitzgerald Marine Reserve

    5.0
    0.89 mi / 46 ft gain
    Located beside a residential neighborhood, Fitzgerald Marine Reserve offers a rare glimpse of life in the northern California intertidal zones. There are parking spaces and restrooms available, as well as ranger-led guided tours. Be sure to check the tide charts and go during low tide (preferab...
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  • Pacifica, California

    Montara Mountain Trail

    5.0
    6.77 mi / 1900 ft gain
    Montara Mountain Trail is a loop trail that takes you through a forest out to ocean views at the top of Montara Mountain. This hike located near Pacifica, California. and can be accessed from Highway 1 as well. If you're looking to do a similar loop hike from the coast, consider Montara Mountain ...
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  • Half Moon Bay, California

    McNee Ranch to Planet of the Apes

    4.88 mi / 1427 ft gain
    McNee Ranch to Planet of the Apes is a 4.8 mile trail located near Montara State Beach that offers ocean views when it is not too cloudy.  You can get amazing views when you hike up above the clouds.  This hike follows one of the main trails up the mountain, but there are many smaller trails to e...
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  • San Bruno, California

    Sweeney Ridge via Sneath Lane

    4.5
    3.88 mi / 646 ft gain
    Starting from the parking lot on Sneath Lane Trail, you’ll head through the gate and continue on the path up Sweeney Ridge. This is a 5.7 mile out-and-back trek. There is a 600 ft. elevation gain, which comes mainly in the first 1.5 miles of the trail. Your legs and lungs may hurt a bit, but if t...
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  • Half Moon Bay, California

    Gray Whale Cove Loop

    5.0
    1.22 mi / 518 ft gain
    Starting at the parking lot adjacent to Gray Whale Cove State Beach, proceed to the start sign indicating "Grey Whale Cove Trail". GWCT is a fun brisk hike with slight elevation gain that should be easy enough to take a small group or even children to. Take note of the tight spaces you may encou...
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  • Half Moon Bay, California

    Gray Whale Cove Trail

    4.5
    2.23 mi / 367 ft gain
    Gray whale cove trail is a splendid, short, and easy hike for the entire family with beautiful ocean views. The starting point is conveniently located near a parking lot that accesses Montara State Beach. From the south end of the parking lot, follow the trail up through the coastal scrub. Within...
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