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

  • Emerald Hills, California

    Sylvan Loop Trail

    2.53 mi / 522 ft gain
    Sylvan Loop Trail is a loop trail where you may see wildflowers located near Redwood City, California.
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  • Emerald Hills, California

    Edgewood Loop

    4.0
    3.29 mi / 607 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

    Cordilleras & Dusty-Footed Woodrat Loop

    3.7
    3.83 mi / 676 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 Cord...
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  • Redwood City, California

    Hassler Loop Trail

    4.0
    1.48 mi / 289 ft gain
    Experience the natural beauty of the San Francisco Peninsula on the scenic Hassler Loop Trail, a 1.5-mile moderately challenging hiking trail nestled in Redwood City's Emerald Hills neighborhood. This beloved local trail offers hikers, nature enthusiasts, and outdoor adventurers a perfect blend...
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  • Redwood City, California

    Whittemore Gulch Trail

    4.0
    6.79 mi / 1791 ft gain
    This trail starts out going downhill towards the ocean for the first half, which makes for a tough end to the hike as you trek back up the ridge.  However, there are nice ocean and hilltop views that are worth the climb. On this trail, you'll pass 60+ banana slugs if conditions are right. They ar...
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  • Redwood City, California

    Whittemore Gulch and Harkins Ridge Loop Trail

    4.6
    6.43 mi / 1772 ft gain
    There are two places to park for this specific loop- the main parking area on Highway 35 (Skyline Boulevard) and a smaller parking lot on the western end of the park. I would recommend parking at whichever is closest. Find directions to both on Openspace.org. From the main parking lot, the trail...
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  • Redwood City, California

    Whittemore Gulch and Purisima Creek Loop Trail

    9.27 mi / 2165 ft gain
    The Whittemore Gulch and Purisima Creek Loop Trail, nestled in the scenic Purisima Creek Redwoods Open Space Preserve near Redwood City, California, is a popular choice for hikers looking for a moderately challenging yet rewarding experience. This 9-mile loop trail winds through lush redwood fo...
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  • La Honda, California

    Peters Creek and Long Ridge

    4.0
    5.5 mi / 1007 ft gain
    From the parking lot, take the connector trail towards the Peters Creek Trail for 0.4 miles. As you descend into a small valley, notice the sound of running water that appears. When you reach the first trail intersection, turn left on the Peters Creek trail. This will give you your first encounte...
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  • Loma Mar, California

    Camp Under the Redwoods at Memorial Park

    With old growth redwoods and a creek swimming area, Memorial Park is a perfect escape from the hustle and bustle of the Bay Area. Memorial Park is only a few miles east of the town of Pescadero. To get here, you can either approach from Highway 1 and drive up Pescadero Creek Road or take Highway ...
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  • Loma Mar, California

    Bike Pescadero Creek County Park

    5.0
    12.5 mi / 1350 ft gain
    Pescadero Creek County Park and the connected Sam McDonald and Memorial Park are located deep in the Santa Cruz Mountains holding a vast network of secluded trails. From biking to backpacking, this area is a perfect place for a day or weekend adventure. This area also has the added bonus having r...
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  • Half Moon Bay, California

    Purisima Creek Trail and Craig Britton Trail Loop

    4.0
    6.95 mi / 1411 ft gain
    This hike is perfect for any time of year, always staying cool because it is near the coast, and there are multiple creeks that flow year-round. Even on foggy days, the fog condenses on trees to make it seem like it is "raining." Be warned that this hike has a lot of elevation change and is stre...
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  • Rancho San Antonio Open Space Preserve, California

    Deer Hollow Farm Trail

    4.0
    2.46 mi / 312 ft gain
    Rancho San Antonio Open Space Preserve has many beginner to intermediate hiking trails.  Deer Hollow Farm Trail Loop is a hiking trail for beginners, families, or anyone wanting to go on a short hike with nice views of the bay. The trail passes by a farm and deer can often be seen wandering arou...
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  • Cupertino, California

    Black Mountain via PG&E, Quarry and Black Mountain Trail

    3.0
    11.72 mi / 3901 ft gain
    Black Mountain via PG&E, Quarry and Black Mountain Trail is an out-and-back trail where you may see wildflowers located near Cupertino, California.
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  • La Honda, California

    Portola Redwoods State Park Loop

    4.8
    8.21 mi / 1924.54 ft gain
    Take in the best of Portola Redwoods State Park: towering redwoods, a waterfall, wildflowers, and a mix of narrow singletrack and wide old logging roads. This loop comes in around 8 miles, with a shorter 5-mile option if you’re looking for something more mellow. Redwood hikes are always a trea...
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  • Half Moon Bay, California

    Southern Beaches at San Gregorio State Beach

    4.0
    1.48 mi / 16 ft gain
    Not a trail per se, but approximately 3 miles (down and back) of beautiful beach to walk down. Lots of interesting caves, wild animals, and rock formations to discover. This is a popular location for sea kayakers. San Gregorio State Beach was originally founded to protect the estuary at the back ...
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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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