San Mateo, California

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

Top Hiking Spots in and near San Mateo

  • San Francisco, California

    San Francisco Crosstown Trail

    5.0
    16.71 mi / 1975 ft gain
    The San Francisco Crosstown Trail runs point-to-point from Candlestick Point to Land End. The SF Crosstown Trail officially opened in 2014.  It connects park trails to neighborhoods and communities.  In it's in entirety it's almost 17 miles long with 5 Sections available for those looking to bre...
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  • Cowell Ranch Beach Access, California

    Cowell Ranch Beach

    5.0
    1.14 mi / 39 ft gain
    Hike half a mile to this beautiful, secluded beach.  There are high cliffs with a steep staircase down to the beach.  The beach has wonderful rock formations on one side.  It is a great place to watch the sunset or bring a picnic.  A great place for a beach day if you are looking for something le...
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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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  • 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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  • 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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  • Daly City, California

    San Bruno Mountain

    4.0
    3.63 mi / 781 ft gain
    San Bruno Mountain is a fun, mellow hike that climbs easily on a well-graded path to the ridge line, and then drops back to the trailhead. Along the way, the trail runs along a creek, ascends through chaparral, and provides excellent views of downtown San Francisco, the East Bay hills, and the Sa...
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  • San Francisco, California

    Bayview Hill Loop

    4.5
    1.24 mi / 184 ft gain
    Bayview Hill Loop is a loop trail that starts with a paved uphill climb and views of the bay facing toward the East Bay located in the Bayview neighborhood of San Francisco, California.
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  • San Francisco, California

    McLaren Park: Philosopher's Way Loop

    5.0
    2.25 mi / 315 ft gain
    Beyond McLaren's family friendly playgrounds and picnic areas, there are miles of trail to explore. The Philosopher's trail is a well-marked loop (notice the stone markings along the trail with arrows etched into them). There are several parking lots available where you can jump onto the loop. No...
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  • Daly City, California

    Mussel Rock Loop

    4.0
    1.95 mi / 322 ft gain
    Mussel rock, a three-story, 50 million year old rock that has been carried some 500 miles northwest from Southern California, is where the San Andreas fault meets the Pacific Ocean. It's also an excellent spot to drink some wine and catch a sunset. From San Francisco, take Highway 1 south towar...
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  • Portola Valley, California

    Windy Hill Loop

    4.3
    7.48 mi / 1578 ft gain
    This 7.2-mile loop starts by heading out of the parking lot and onto the Spring Ridge Trail. Head Southeast On Spring Ridge Trail until you connect with Hamms Gulch Trail. When you jump on Hamms Gulch, head southwest for ~3.4 miles as you circle the far end of the OSP. At this point, you will con...
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  • Portola Valley, California

    Windy Hill via Anniversary Trail Loop

    0.89 mi / 164 ft gain
    To get a good viewing point for the sunrise, take a quick on the Anniversary Trail up to Windy Hill. This is a real bang-for-your-buck adventure as the trail isn't too long and you get to see a spectacular sunrise combined with great views of both the Bay Area and out towards the ocean. Note tha...
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  • Portola Valley, California

    Windy Hill: Spring Ridge, Anniversary Loop

    5.0
    6.18 mi / 1421 ft gain
    There are a few options to hiking Windy Hill Open Space Preserve. 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...
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  • San Francisco, California

    Bernal Heights Park

    4.7
    0.95 mi / 128 ft gain
    Bernal Heights Park is an excellent week night adventure for those who need an escape from the city. Sit atop this small, grassy peak in peace and look out over the San Francisco skyline. Park on the street bordering the park and follow a pathway that leads up to the top. You will be instantly g...
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  • Palo Alto, California

    Arastradero Preserve: Juan Batista & Meadowlark Loop

    3.0
    4.65 mi / 597 ft gain
    Getting There: From Hwy 280, take the Page Mill Road exit and head West on Page Mill Road, away from Downtown Palo Alto (if you're taking 101, exit on Oregon Expressway). Then turn right on Arastradero Road. There will be a small sign indicating the dirt parking lot on the eastern side of the st...
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  • San Francisco, California

    Lake Merced Loop

    4.7
    4.53 mi / 180 ft gain
    Lake Merced Loop is a loop trail in the southwestern part of San Francisco. This trail is used for running and walking. You'll see plenty of people getting exercise or taking their dog for a stroll. There are also benches and tables around the loop. The lake itself is fresh water and is used for...
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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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