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Cupertino, California

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

Top Chillin Spots in and near Cupertino

  • Santa Cruz, California

    Surf at Natural Bridges State Beach

    4.5
    Natural Bridges is off of West Cliff Drive to the north of popular Santa Cruz break, Steamer Lane. The break is a right point break, which breaks on a rocky shelf and reef. The break is best during sizable swells (NW, SW, and West) and a low tide. Be sure to check the wind, this break gets blown ...
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  • Livermore, California

    Del Valle Regional Park

    4.0
    Looking for a quick summer escape filled with stand up paddling, canoeing, fishing, hiking, and picnics? Look no further than Del Valle Regional Park. Consistently considered one of the best campgrounds in the Bay Area, the centerpiece of Del Valle is a 5-mile long lake that allows swimming, fish...
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  • Half Moon Bay, California

    Catch the Sunset at Maverick's Beach

    5.0
    1 mi
    Maverick's beach is most well-known for the Maverick surf competition and the gnarly waves which surface here in the winter months. For the rest of the year, the beach is still a site to see. With huge waves crashing ¼ mile off shore and bluffs towering 100 feet above you, it’s a picturesque plac...
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  • Moss Beach, California

    Cypress Tree Tunnels at Moss Beach

    4.5
    0.79 mi / 105 ft gain
    The Cypress Tree Tunnels are a quick jaunt from San Francisco (22 miles) and make for a great half-day trip. Getting here depends on traffic, but 30 minutes from the center of the city is doable. Parking is relatively easy. You can either park at the south end of the area at the Cypress Cove entr...
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  • Moss Beach, California

    Fitzgerald Marine Reserve

    5.0
    0.89 mi / 46 ft gain
    Located beside a residential neighborhood, Fitzgerald Marine Reserve offers a rare glimpse of life in the northern California intertidal zones. There are parking spaces and restrooms available, as well as ranger-led guided tours. Be sure to check the tide charts and go during low tide (preferab...
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  • Half Moon Bay, California

    Devil's Slide Bunker

    4.3
    The Devil's Slide Bunker is perched out on a point the defiantly juts out into the ocean. The Bunker is covered in constantly changing graffiti, which provides a stunning contrast to the gorgeous seaside. Hop on Highway 1 South. Just south of Pacifica there is a tunnel. Once you go through the t...
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  • Pacifica, California

    Surf at Pacifica State Beach

    4.5
    If you're looking for a place to surf and Ocean Beach isn't quite your speed or Santa Cruz is too far, head to Pacifica, specifically Linda Mar. Linda Mar is usually more wind protected and user-friendly than ocean beach. Break out your longboard or hybrid board and head to this beach. There is e...
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  • Pacifica, California

    Picnic at Sharp Park Beach

    4.0
    A medium size beach with darker sand with big rocks and a paved path for walkers and joggers.  The beach is a great place to bring a picnic and watch the sunset.  It is located next to Pacifica Pier, which is popular for fishing.
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  • Pacifica, California

    Fish at Pacifica Pier

    5.0
    This is a great place for fishing or just taking a walk to watch the sunset.  It's a great place to walk or jog, or even bring a pup!  There are lot of people fishing throughout the pier.   A short walk away is Sharp Park Beach, where you can relax and bring a picnic to watch the sunset.
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  • Oakland, California

    Hike Redwood Regional Park via the Dunn Loop

    5.0
    3.6 mi / 606 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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  • Daly City, California

    Mussel Rock Loop

    4.0
    1.95 mi / 322 ft gain
    Mussel rock, a three-story, 50 million year old rock that has been carried some 500 miles northwest from Southern California, is where the San Andreas fault meets the Pacific Ocean. It's also an excellent spot to drink some wine and catch a sunset. From San Francisco, take Highway 1 south towar...
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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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  • 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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  • 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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