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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

  • Pescadero, United States

    Relax at Costanoa Lodge

    3.0
    Looking for a quick escape from the city, but sleeping on the ground isn’t really your thing? Look no further than Costanoa Lodge in Pescadero, an upscale "glamping" experience just an hour south of San Francisco with tons of hiking options. This is a really fun option for anyone who enjoys being...
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  • Davenport, California

    Hike around Greyhound Beach and Climb Greyhound Rock

    0.7 mi / 0 ft gain
    The trailhead is at the Greyhound Rock State Marine Conservation Area which is directly off Highway 1. There is a large paved parking lot with a good amount of trees so finding a shady parking spot isn't that difficult (if that's important to you). The parking lot is located on the beach cliffs ...
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  • Belmont, California

    Hike San Mateo's Sugarloaf Mountain

    5.0
    1.5 mi / 500 ft gain
    Sugarloaf is tucked away in Laurelwood Park which is located in a residential neighborhood right off of Hwy 92 in San Mateo, making this a great hiking & trail running option for Peninsula residents.I always park on Glendora Dr. and follow the paved path down towards the playground. At the bo...
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  • Mount Hamilton, California

    Stargaze at Lick Observatory

    3.8
    Hop on Road 130 heading out of San Jose and follow the winding two lane road up, up, up to to the top of Mt. Hamilton and the Lick Observatory. There are lots of deer, wild turkey, and pigs in the area. If you are lucky you will get to see a herd of deer grazing in a meadow. But be careful that y...
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  • Santa Cruz, California

    Hike the Rincon Fire Trail

    5.0
    1 mi / 300 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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  • Pescadero, California

    Catch a Sunset at Bean Hollow State Beach

    5.0
    There are a bunch of places to photograph this beach if you head north on the trail that runs along the beach.There is parking at the beach but it can fill up quickly!The only warning you need is about the tide. Make sure you are watching it the entire time because it can creep up on you and will...
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  • Pescadero, California

    Explore the Pidgeon Point Lighthouse

    5.0
    Pidgeon Point Lighthouse is conveniently located just 50 miles south of San Francisco. Constructed in 1872 and standing at 115 feet, it is among the tallest lighthouse in America.Part of the state park system, it is surprisingly secluded. Numerous parking space were available in the lot with hand...
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  • Pescadero, California

    Exploring Big Sur to Pigeon Point

    We started off in Big Sur and took as many pull-off viewpoints as possible between Big Sur and the final destination, Pigeon Point Lighthouse. The weather was foggy in some spots but would open up to reveal the vast Pacific Ocean and sun in others. The weather was mild for us but we're familiar w...
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  • Cowell Ranch Beach Access, California

    Picnic at Cowell Ranch Beach

    5.0
    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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  • Half Moon Bay, California

    Bike the Cowell-Purisima Coastal Trail

    4.0
    This trail begins at the Cowell State Beach parking lot and is only open on the weekends. From the lot, take the short Cowell Ranch Access trail to a scenic overlook. There are steps down to the secluded pocket beach just above the main trail. The trail playfully meanders along the cliffside with...
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  • Davenport, California

    Beach Picnic at 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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  • Santa Cruz, California

    Explore Panther Beach

    4.5
    Panther Beach's white sand, clear water, and interesting rock formations make it one of the most stunning beaches along this stretch of CA1. But this is a hidden gem for a reason - there are no signs along CA1 for Panther Beach. You need to keep you eyes peeled for cars parked along the side of t...
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  • Half Moon Bay, California

    Hike Along the Half Moon Bay Coastal Trail

    4.6
    5 mi / 104 ft gain
    Start at the visitor center along Kelly Avenue. Take note that the day parking fee is $10 in 2016 for each vehicle. You will then be able to enjoy both the Coastside Trail and Francis Beach (plus other beaches) with access to the amenities such as coin-operated showers and a semi-private beach.Th...
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  • Santa Cruz, California

    Bonfire at Seabright State Beach

    5.0
    This is a wide, beautiful beach that's an amazing spot to spend the day and enjoy a bonfire at night. Seabright is probably the most popular spot in Santa Cruz for a bonfire, due to its convenient proximity to the Beach Boardwalk. But luckily, this beach is tucked in between the San Lorenzo River...
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  • Santa Cruz, California

    A Beach Bonfire in Santa Cruz at Twin Lakes SB

    This one-mile stretch of beach is the perfect option for those looking for a peaceful Santa Cruz experience, but without the crowds. The beach features soft sand, playful surf, an awesome view of Walton Lighthouse, and a handful of fire pits to choose from. It's a great spot to spend the entire d...
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  • Santa Cruz, California

    Beach Day at Lighthouse Field State Beach

    4.0
    This beach is less crowded compared to other beaches in Santa Cruz.  I got there early on a Saturday and found easy street parking.  There was plenty of space to spread out on the soft sand.  Later in the day I saw dolphins several times!  This is close to the Santa Cruz Surfing Museum.  It’s als...
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