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San Jose, California

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

Top Chillin Spots in and near San Jose

  • 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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  • Moss Landing, California

    Whale Watching off Moss Landing

    The Monterey Bay National Marine Sanctuary is home to some of the most diverse and rich waters in our oceans, and you have the chance to see it up close and personal! The big prize is getting to see a whale, but these waters are teeming with other wildlife from dolphins to otters to sea lions.  F...
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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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  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • 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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  • Clayton, California

    Hike the Waterfalls of Mount Diablo Loop Trail

    5.0
    6 mi / 1627 ft gain
    Winter and spring rains create scenic waterfalls in this hike at Mount Diablo, the East Bay's signature peak. Be careful hiking immediately post-rain, watch for slippery sections of mud. The trail is moderately difficult and is used by hikers, walking groups, trail runners, and for nature trips. ...
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