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Los Gatos, California

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

Top Chillin Spots in and near Los Gatos

  • Pacific Grove, California

    Catch Sunset on Asilomar State Beach

    Asilomar, or “refuge by the sea” definitely lives up to its name. The beach is expansive and less-populated than other nearby destinations. With large sandbars and rocky outcroppings, it is a great place to enjoy sunset.  This beach is also known for its premium surf, so expect a show from the lo...
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  • Pacific Grove, California

    Bike at Asilomar State Beach

    At Asilomar State Beach, adventure is accessible in many forms. I had the opportunity to rent a bike from Adventures by the Sea. Rentals start at $25, and while you are not permitted to ride along the boardwalk that leads you to the beach, you may walk your bike through the exquisite sand dunes A...
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  • Pacific Grove, California

    Exploring Asilomar's Ancient Sand Dunes

    4.0
    Asilomar State Beach covers 107 acres of land. It is home to a delicate ecosystem that has been sustained through the years after it was almost destroyed. The intricate dunes at Asilomar are what have survived after the over-grazing back in the early 1900's that damaged about 480 acres of dunes. ...
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  • Pacific Grove, California

    Play Volleyball at Asilomar Conference Grounds

    Asilomar translates to “refuge by the sea,” a phrase that accurately depicts the Asilomar Conference Grounds. The area started as a YWCA women’s empowerment camp in 1913 and has since transitioned into a well-preserved state beach. It is located in the beautiful Monterey Peninsula.  If you find y...
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  • Livermore, California

    Condor, Volvan, Stone Corral, Coyote Loop

    4.5
    4.38 mi / 620 ft gain
    This regional preserve is perfect for day hikes. There are also designated campsites and even a backpack campsite. Horses and dogs are welcome in the preserve. There are many different clearly marked trails that one can choose from. A good 4.5 mile loop is to start at the Park Residence entrance...
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  • Del Monte Forest, California

    Relax at Spanish Bay

    Spanish Bay is a beach with a view point at the southern tip.  You can see waves crashing into rocks and the many different shades of blue.  This is a great spot for anyone exploring 17 Mile Drive, as it is scenic and perfect for picnics.  There is a golf course nearby that offers some of the mos...
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  • Monterey, California

    Sail on Monterey Bay

    Few places along the California coast are perfectly suited for a day of sailing. While San Diego, Santa Barbara, Santa Monica, Long Beach, San Francisco, and Catalina Island offer sailing adventures, none of them offer wide open Pacific waters without dangerous commercial traffic to navigate. The...
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  • San Francisco, California

    Swing at Billy Goat Hill

    3.5
    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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  • San Francisco, California

    Park Day at Dolores Park

    4.0
    If the sun is shining, and you’re in the mood for playing around with friends in one of SF’s many amazing parks, Dolores should be at the top of your list. With amazing views of downtown, huge tiered lawn areas, tennis courts, basketball courts, a brand new playground, and easy access to some of ...
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  • San Francisco, California

    Catch a Sunset at 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 luck...
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  • San Francisco, California

    Take a Ride on the 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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  • Walnut Creek, California

    Camp at Juniper Campground in Mount Diablo SP

    Mount Diablo's summit in Mount Diablo State Park rises to 3,848ft, with Juniper Campground in Mount Diablo SP is at approximately 3,000ft in elevation.  Juniper Campground overlooks the valley below and some of the San Francisco Bay.  Reservations for Juniper Campground can be made at Reserveamer...
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  • Walnut Creek, California

    Sugarloaf Open Space Loop

    1.91 mi / 243 ft gain
    Sugarloaf Open Space Loop is an almost 2-mile loop for hiking, running and walking. This trail is relatively easy and takes under one hour to hike. This loop is dog friendly. 
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  • Del Monte Forest, California

    Explore Highway 1 from Carmel to Big Sur

    4.6
    Being from the Central Coast, every time I visit the area I like to do the same trip - Simply because it is amazing. The trip starts along 17 mile drive located in Carmel. From the road, you see the Central Coast icon, the Lone Cypress. Being one of the most photographed trees in North America, i...
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  • San Francisco, California

    Visit the 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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  • Walnut Creek, California

    Castle Rock Trail

    5.0
    6.06 mi / 971 ft gain
    Located near Walnut Creek, the trail is easily accessible from anywhere in the Bay Area. The trail is kept open year-round, and happens to be part of the American Discovery Trail and the Coast to Crest trail. If you are not done hiking, connecting trails allow you to summit Mt. Diablo.  This tra...
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