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

  • San Francisco, California

    Mount Davidson

    4.5
    1.03 mi / 299 ft gain
    Mount Davidson Park is located in the southwestern part of the city nestled between Diamond Heights and Portola Dr. The climb isn't too difficult, but to reach the top of the 928ft summit, you should wear close-toed shoes and be ready for some loose gravel or mud if it's been raining. The hike is...
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  • San Francisco, California

    Fort Funston Trail

    4.7
    1.81 mi / 253 ft gain
    Fort Funston is an SF gem I discovered when looking for a dog friendly hike near the city. Located west of Lake Merced, you'll find a gorgeous Northern California beach oasis where you and your dog can run wild and free :). Parking is located at the top of the park where you'll descend a steep se...
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  • San Francisco, California

    Twin Peaks Loop

    4.0
    2.04 mi / 259 ft gain
    There are a ton of ways to get here (and obviously that can affect the total distance) but this is starting from Clarendon. Follow along up Twin Peaks boulevard where you'll see the peaks upon your approach. Keep an eye out for traffic as there may be visitors driving toward and away from Twin Pe...
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  • San Francisco, California

    Fairy Gates Trail

    5.0
    0.89 mi / 328 ft gain
    Fairy Gates Trail is an out-and-back trail that takes you through a nice forest located near San Francisco, California.
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  • San Francisco, California

    Twin Peaks and Mt. Sutro Loop

    4.2
    5.26 mi / 1145 ft gain
    Are you thinking, hit up two of the bigger peaks in SF, what a great idea? Well, you thought right! The first mile and a half is uphill as you charge to the top of Twin Peaks. This 6% grade leads to a 460 ft elevation gain. The good news is, if it's not foggy, the views of the bay are stunning, e...
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  • San Francisco, California

    Grand View Park ("Turtle Hill")

    5.0
    0.21 mi / 7 ft gain
    A recipe for happiness in the "cool grey city of love." To the seasoned San Franciscan there is no finer view in the Bay Area than that from San Francisco's front porch, Turtle Hill or "Grand View Park". If the North American continent / plate is a ship, then Grand View Park is the prow giving e...
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  • San Francisco, California

    16th Avenue Tiled Steps

    4.6
    0.09 mi / 79 ft gain
    The 16th Avenue Tiled Steps also known as the Moraga steps are an impressive community achievement, and an equally killer workout. Take an easy lap up the stairs to check out the amazing art, take in the views from the top, then get down to business. You'll be glad you made the trek over to this ...
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  • Walnut Creek, California

    Juniper to the Summit Loop Trail and Meridian Ridge

    6.56 mi / 2037 ft gain
    Juniper to the Summit Loop Trail and Meridian Ridge is a loop trail that is strenuous located near Diablo, California.
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  • San Francisco, California

    Hidden Garden Steps

    4.3
    0.1 mi / 39 ft gain
    These tiles steps are ironically iconic, as they are called the "Hidden" Garden Steps.  They are one of 3 tiled staircases that San Francisco is famous for. The others are the 16th Ave Tiled Steps and the Lincoln Park Steps. Tip: When calling an uber, try to get dropped off at the top of the ste...
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  • San Francisco, California

    Coit Tower Stairs

    3.8
    0.49 mi / 200 ft gain
    There are 2 sets of stairs for Coit Tower on Sansome St. The first set is at Greenwich and the second is at Filbert. The Filbert steps are a little deeper per step and are mostly wood and concrete. The Greenwich steps are a little tougher because of the shallower, brick stairs as you get toward t...
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  • Berkeley, California

    Stonewall Panoramic Trail

    4.5
    1.44 mi / 663 ft gain
    From the trailhead at Stonewall Road, the 1.5-mile trail makes for an excellent before or after-work run. But the steep hills and loose ground aren’t for those looking to find an easy nature walk. The incline starts well before the Stonewall-Panoramic trailhead, so you won’t even have time to w...
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  • San Francisco, California

    Stow Lake And Strawberry Hill

    4.9
    2.09 mi / 253 ft gain
    Strawberry Hill is one of the hidden gems of Golden Gate Park. It is named after the once abundant strawberry fields that inhabited the island. The hill, which reaches up to 430ft, is located in the middle of Stow Lake and has 2 foot bridges for access. This is a great place to run if you're look...
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  • Lafayette, California

    Lafayette Reservoir via Nature Area Rim Trail

    5.0
    5 mi / 758 ft gain
    Lafayette Reservoir is perfect for canoeing, mountain biking, trail running, and hiking. The Reservoir trail system is also used for nature walks and birding. The loop has several high points that have amazing views. The trails become very muddy after wet weather - so tread with caution.  Th...
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  • Walnut Creek, California

    Run the Mt. Diablo Foothill Loop

    5.0
    6.2 mi / 875 ft gain
    Continue by car down Castle Rock Road until it dead ends at the beginning of the trail. Parking is usually easy to find. If full, there is another overflow lot about 500 ft back the way you came in.You'll walk a good half mile down the trail before getting the main gate. As you're walking, you'll...
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  • Walnut Creek, California

    Castle Rock Trail

    5.0
    6.06 mi / 971 ft gain
    Located near Walnut Creek, the trail is easily accessible from anywhere in the Bay Area. The trail is kept open year-round, and happens to be part of the American Discovery Trail and the Coast to Crest trail. If you are not done hiking, connecting trails allow you to summit Mt. Diablo.  This tra...
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  • San Francisco, California

    Lover's Lane, Ecology, Mountain Lake Trail Loop

    4.5
    2.04 mi / 344 ft gain
    Tucked into a corner of the Golden Gate National Recreation Area is the Presidio, a beautiful little oasis of forests, beaches, and sweeping views that locals love. While the coastal trails get most of the attention here, the park covers 300 acres of prime real estate with lots of notable attract...
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