Portola Valley, California

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

Top Hiking Spots in and near Portola Valley

  • 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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  • Woodside, California

    Meadow & Bear Gulch Loop

    5.0
    4.57 mi / 1089 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 ...
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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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  • Los Altos, California

    Foothills Park: Boronda Lake

    3.0
    0.93 mi / 0 ft gain
    Situated in the hills above Palo Alto; Foothills Park is the perfect spot to spend the day outdoors. With hiking, fishing, picnic areas, wide open fields, and expansive views of the Bay Area, this hidden gem is a must visit. Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After ...
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  • Redwood City, California

    Old Growth Redwood Loop

    4.4
    5.68 mi / 1480 ft gain
    This hike starts at the parking lot of the El Corte de Madera Open Space Preserve. The lot is located roughly a mile south on Skyline Boulevard from the Skeggs Point Vista. From the parking lot, take the Methuselah Trail for 0.3 miles until you reach the Timberview Trail. Take this trail for anot...
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  • Redwood City, California

    Crystal Springs Trail Loop

    4.0
    5.4 mi / 1227 ft gain
    This is a great hike for any season of the year, with rushing streams during the winter, wildflowers in the spring, and cool, shaded canyons during the summer. Starting from near the Zwierlein Picnic area, take the Crystal Springs to the left into the redwood forest. Stay straight at the next tr...
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  • Redwood City, California

    Stulsaft Park Loop

    4.0
    0.91 mi / 98 ft gain
    Stulsaft Park Loop in Redwood City, California, is a scenic and family-friendly 0.9-mile loop trail, ideal for hiking, walking, and running. This is a relatively easy stroll with only 98 feet of elevation gain and is accessible for people of all fitness levels. This trail is also particularly pop...
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  • Los Altos, California

    Stevens Creek & Canyon Loop

    4.5
    2.77 mi / 446 ft gain
    This hike is best done in the late fall, winter, and spring so that the creek is running and the hills are green. Starting at the preserve parking lot, the first half of the hike is predominantly downhill. At the main trailhead, start in the direction of the Stevens Creek Nature Trail, as told by...
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  • Los Altos, California

    Black Mountain and Stevens Creek Canyon

    4.0
    5.47 mi / 1066 ft gain
    This hike can be done during any season, but for the creek to be running and for more comfortable temperatures, it is best to go on a cool winter or spring day. Starting at the preserve parking lot, take the Stevens Creek nature trail, allowing you to witness spectacular views of a large, forest...
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  • Redwood City, California

    Russian Ridge Loop

    4.5
    5.45 mi / 837 ft gain
    Russian Ridge offers a great place to jump on the trail and in the right season, see some of the best wildflowers blooming. On top of that, you get access to amazing views from the ridge. Once you get your parking space, jump on the Ridge Trail and start gaining a little elevation while you head...
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  • Redwood City, California

    Methuselah and El Corte De Madera Creek Loop

    6.5 mi / 1778 ft gain
    This loop hike will provide people with the opportunity to experience the tranquility of the lower canyons of the preserve, which tend to be more isolated than the heavier-trafficked trails that are closer to the main highway. Be warned that this hike is fairly strenuous because of the large amo...
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  • Santa Clara County, California

    Black Mountain via Rhus Ridge Trail

    9.75 mi / 2992 ft gain
    Just outside of Los Altos is a very long ridge of mountains, one of which is Black Mountain.  This is a very dry hike, with no tree canopy, so it can get very hot! Be aware that this can make the hike feel a lot more difficult with the sun beating down on you. Follow Rhus Ridge Trail to Black Mo...
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  • La Honda, California

    Brook Trail Loop

    7.63 mi / 1457 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 trailhea...
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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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