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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

    Hike the Windy Hill Loop

    4.3
    7.2 mi / 1400 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

    Sunrise Hike at Windy Hill

    5.0
    There are a few options to this hike. 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, but the main parking lot i...
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  • Woodside, California

    Hike through Wunderlich County Park

    5.0
    4.5 mi / 1400 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 o...
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  • Palo Alto, California

    Hike the Arastradero Preserve Loop

    3.0
    4.5 mi / 600 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 str...
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  • Los Altos, California

    Park Day at Foothills Park

    1.7
    Disclaimer: Foothills Park requires proof of residence in Palo Alto or being accompanied by a resident of the city. Learn more here.Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After exiting you take a short scenic drive up the hill and come to the park entrance on your right...
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  • Redwood City, California

    Hike or Bike the Old Growth Redwood Loop at El Corte de Madera

    4.4
    8.8 mi / 1900 ft gain
    This hike starts at the middle parking lot of the El Corte de Madera Open Space Preserve. The middle 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 ...
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  • Redwood City, California

    Hike the Crystal Springs Trail Loop

    5.6 mi / 1300 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 tra...
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  • Los Altos, California

    Hike the Monte Bello Open Space Preserve Loop

    4.5
    2.9 mi / 600 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

    Hike to Black Mountain and Stevens Creek Canyon

    4.0
    6 mi / 950 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, foreste...
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  • Redwood City, California

    Hike Russian Ridge

    4.5
    4 mi
    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 hit your parking space, add a little extra warm up before jumping on the trail to make this 3.7-mil...
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  • Redwood City, California

    Hike the Methuselah and El Corte De Madera Creek Loop

    6.2 mi / 1800 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 amou...
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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

    Hike the Brook Trail Loop

    7.1 mi / 1500 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 trailhead...
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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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  • Redwood City, California

    Hike Edgewood Park and Natural Preserve

    4.0
    4.2 mi / 600 ft gain
    Edgewood Park and Natural Preserve rests in San Mateo County, California. The sweeping hillsides exemplify the true native flora of California, as the foundation of rock and soil is poor in nutrients. Only a few specialized native plants are adapted to live here--don't miss the unique wildflower ...
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  • Redwood City, California

    Hike the Pulgas Ridge Open Space Preserve Loop

    3.7
    5.5 mi / 1000 ft gain
    Getting there: exit Highway 280 at Edgewood Road, travel .75 miles east, turn left on Crestview Drive, then immediately left again on Edmonds Road.Once parked, there are several different path options through the park. All of them connect in a large loop, and return to the parking lot. The Cordil...
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