Portola Valley, California

Looking for the best chillin 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 Chillin Spots in and near Portola Valley

  • Felton, California

    Redwood Grove Loop

    4.0
    0.93 mi / 144 ft gain
    Henry Cowell Redwoods State Park is located just a few miles north of the city of Santa Cruz, along Highway 9. The park is home to an array of hiking and biking trails, but the crown jewel of the park is the Redwood Grove Loop Trail, which is only a 1/4 mile in from the park's entrance. Many peo...
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  • Davenport, California

    Old Davenport Pier

    5.0
    The ruins of Davenport Pier are located on Davenport Pier Beach, just north of Davenport on Highway 1, which is about 11 miles north of Santa Cruz. The pier was never completed and the support system for it was left on the beach, the first pillar arch has had a chain swing added to it and can be ...
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  • Davenport, California

    Shark Fin Cove

    4.3
    Shark Fin Cove is a large rock formation in an inlet off Highway 1 in Northern California. It is located 1 mile south of Davenport and 10 miles north of Santa Cruz. There is a sizable parking lot located on the side of Highway 1 to park in. Walk down the path left of the parking lot and cross the...
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  • San Francisco, California

    Billy Goat Hill

    4.0
    Billy Goat Hill Park is located in the Glen Park neighborhood of San Francisco. The park has street parking at the top of the park on Beacon Street or at the base of the park on Ladley Street. Getting to the swing is only a short walk up or down the stairs that run through the middle of the park....
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  • Scotts Valley, California

    Panther Beach

    5.0
    0.27 mi / 22.97 ft gain
    Panther Beach: Santa Cruz's Hidden Coastal Gem Panther Beach is a stunning, secluded beach nestled among rocky cliff sides along California's Highway 1. This is a great place to catch an awesome sunset, and there's even some decent bouldering on the beach archway for climbing enthusiasts. Beach...
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  • Santa Cruz, California

    Rincon Fire Trail to San Lorenzo River

    5.0
    1.42 mi / 328 ft gain
    The Rincon Fire Trail Starts at a small dirt parking lot next to CA-9 and traverses down the mountain to the San Lorenzo River Connecting with the Pipeline Trail. The trail can be a simple one of a mile out and back or up to 5 miles depending on your preference. The elevation will change by about...
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  • San Francisco, California

    Dolores Park

    4.1
    Mission Dolores Park spans two city blocks in San Francisco's Mission District, offering 16 acres of recreational space with stunning city skyline views. This historic park, established in 1905, serves as a cultural hub and outdoor gathering space for both locals and tourists. Location & A...
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  • San Francisco, California

    Twin Peaks

    4.6
    Most locals have heard of Twin Peaks, so if you hop in an Uber or Taxi you should be just fine. If not or you are driving yourself, head for Twin Peaks Boulevard, then just follow it to the top. Voila! When you're there, be sure to catch a sunset, as it is absolutely breath-taking, If you are lu...
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  • San Francisco, California

    Seward Street Slides

    4.2
    Tucked away in a small neighborhood park in Eureka Valley is a set of really fun, slippery, and surprisingly steep concrete slides. They were originally designed by a 14 year old kid over 30 years ago, and we all owe him a big hat tip. People use a variety of sliding materials (saucers, food tray...
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  • San Francisco, California

    Sunset Reservoir

    0.69 mi / 62.99 ft gain
    Hidden in the Sunset District, the Sunset Reservoir is more than just piece of city infrastructure — its surrounding paths make for a convenient urban stroll with peaceful views, a solar rooftop, and surprising vistas of San Francisco. Trail & Walk Details Many local walkers estimate the fu...
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  • Oakland, California

    Dunn Loop

    5.0
    3.08 mi / 758 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

    Conservatory of Flowers

    4.7
    Spend a day exploring Golden Gate Park by jogging, cycling, or leisurely strolling.  There are so many fantastic stops in the park including a variety of lakes, playgrounds, a golf course, the California Academy of Science, the Conservatory of Flowers, and much much more!  It is definitely worth ...
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  • San Francisco, California

    Ina Coolbrith Park

    5.0
    This tucked away neighborhood gem is less than a square block in size, but offers some of the best views of San Francisco. After a quick, but steep, 5 minute walk, you'll be rewarded with incredible views of: the city skyline, Coit Tower, Alcatraz, and the Bay Bridge. There are a few benches avai...
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  • San Francisco, California

    Beach Bonfire at Ocean Beach

    4.3
    Yes, it's often cold in the city. So, what's the best way to warm up? Bring some blankets, a jacket or two, and come out to Ocean Beach to enjoy a bonfire, a sunset, and some quality time with friends. The fire pits are between Fulton and Lincoln. On a sunny day, get there early if you want to ge...
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  • San Francisco, California

    Sutro Baths Ruins

    4.5
    0.46 mi / 115 ft gain
    Whether you simply look down on the ruins from the [conveniently located] parking lot above, or choose to walk down the stairs and explore, you will be greeted with stunning views of the Baths, and the Pacific Ocean stretching infinitely beyond. The highlight of any trip to the Sutro Baths is ...
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  • San Francisco, California

    The Wave Organ

    The Wave Organ is an acoustic sculpture located on a jetty in the Marina district of San Francisco. Designed by Peter Richards and built in collaboration with sculptor George Gonzalez, this unique attraction was completed in 1986. It utilizes the natural movement of the waves to create a variety ...
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