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Woodside, California

Looking for the best running in Woodside? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Woodside. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Running Spots in and near Woodside

  • 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 Francisco, California

    Glen Canyon Park Trail

    5.0
    1.76 mi / 394 ft gain
    Glen Canyon Park Trail is a loop most commonly used for running or hiking in the southwestern side of San Francisco, California. Parking for the loop is street parking, so be sure to take any valuables out of the car with you.  Note: There are restrooms available at the Glen Canyon Recreation Ce...
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  • 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 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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  • 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 Jose, California

    Hike the Quicksilver Trail

    4.3
    5.1 mi / 915 ft gain
    The trails are well maintained and offer good visibility. The trail can be muddy after it rains, and does not have much shade (so bring extra water in the summer).  Dogs are allowed on this trail but must be kept on leash. Keep your eyes peeled for wildlife - this trail is frequently used for bir...
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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

    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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  • San Francisco, California

    Twin Peaks and Mt. Sutro Loop

    4.2
    6 mi
    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

    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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  • Oakland, California

    Hike Redwood Regional Park via the Dunn Loop

    5.0
    3.6 mi / 606 ft gain
    The Redwood Regional Dunn Loop is just outside of Oakland, and can be reached from anywhere in the Bay Area for a fun day or half-day trip. The trail is open year-round. In the spring, wildflowers are abundant. The trail has a great mix of sun and shade. Dogs are allowed, but must be kept on leash. 
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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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  • Oakland, California

    Run the Circumnavigation of Redwood Regional Park's Ultimate Trail Loop

    5.0
    7.5 mi / 1600 ft gain
    It’s difficult to have a car in San Francisco, but oh-so worth it when it comes to weekend getaways, especially with all the Bay Area has to offer. This is a super accessible trail system just 30 minutes outside of the city that makes for a fun, easy trail run or hike.Redwood Regional Park, part ...
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  • San Francisco, California

    Run the Coit Tower Stairs

    3.8
    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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  • 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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