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Oakland, California

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

Top Chillin Spots in and near Oakland

  • Loma Mar, California

    Bike Pescadero Creek County Park

    5.0
    12.5 mi / 1350 ft gain
    Pescadero Creek County Park and the connected Sam McDonald and Memorial Park are located deep in the Santa Cruz Mountains holding a vast network of secluded trails. From biking to backpacking, this area is a perfect place for a day or weekend adventure. This area also has the added bonus having r...
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  • Sonoma, California

    Sonoma Valley Wine Tour Bike Ride

    This 12 mile bike path starts at a rental shop in Sonoma Country called Sonoma Valley Bike Tours and Rentals. Follow the trail through the quaint residential area and into the back country vineyards and dirt trails. This ride can be anything between a hardcore 2 hour cycling workout with a few in...
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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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  • Point Reyes Station, California

    Sky Trail Loop

    5.0
    9.55 mi / 1818 ft gain
    Sky Trail in Point Reyes National Seashore is a dramatic, mostly single-track trail that runs along the main spine of the Inverness Ridge and across highest mountains in Point Reyes, looming above the Olema Valley and Highway 1 which mark the San Andreas Fault rift zone and the dividing line betw...
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  • Point Reyes Station, California

    Sky Campground via Sky Trail

    2.66 mi / 495 ft gain
    Entering Point Reyes National Seashore from Bear Valley Road the Sky Trailhead is a 4.9 mile drive.  Camping in Sky Camp requires a Camping Permit.   Once at the Sky Trailhead parking lot.  The Sky Trailhead will be on the left side pulling in.  The hike is not very strenuous and not all that lo...
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  • Petaluma, California

    Hike Helen Putnam Regional Park

    4.0
    6 mi / 550 ft gain
    A 216-acre park, Helen Putnam offers 9 trails that are relatively short but can be combined however you wish. Go 2 miles or 10 miles. Loop in and out, up or around. I take a different route every time I hike here.For a good 6-mile hike, begin at the southwest corner, where the parking lot and res...
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  • Pescadero, California

    Hike the Canyon Rim Route in Butano State Park

    5.0
    11.7 mi
    Located deep within the Santa Cruz Mountains, Butano State Park boasts a large redwood canyon with many miles of hiking trails as well as campsites. This state park is one of the quietest and least visited parks on the peninsula making a perfect place to escape the hustle of the Bay Area Butano S...
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  • Inverness, California

    Walk along Limantour Beach

    4.8
    The entire drive to Pt. Reyes is picturesque, but once you make it to Limantour, you and your dog can both get out and enjoy it! This area, between Drake's Bay and an estuary, allows you to spend time relaxing or head out for a run (keep the dog on leash). If you're lucky you might either get a c...
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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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  • San Jose, California

    Hike the Quicksilver Trail

    4.3
    5.1 mi / 915 ft gain
    The trails are well maintained and offer good visibility. The trail can be muddy after it rains, and does not have much shade (so bring extra water in the summer).  Dogs are allowed on this trail but must be kept on leash. Keep your eyes peeled for wildlife - this trail is frequently used for bir...
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  • 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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  • 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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  • Inverness, California

    Hike the Estero Trail

    5.0
    8 mi / 200 ft gain
    June sunshine blazes on your shoulders during this scenic stroll through the Point Reyes Seashore. The trail is alive and awash with colorful wildflowers around every corner.Beginning at the trailhead, just off Home Ranch Road, with a convenient parking lot and bathroom, you'll wade through a hal...
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  • Point Reyes Station, California

    Drake's Beach, Pt. Reyes

    5.0
    Named after the famed explorer, Sir Francis Drake, Drakes Beach is part of the scenic Point Reyes National Seashore. If you're looking to spend a day and an evening at the beach, grab some snacks and some firewood and head out to Drakes Beach. Key things to remember with the bonfire: Build th...
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  • Yountville, California

    Bike the Napa Valley Wine Trail

    12.5 mi / 100 ft gain
    The Napa Vally Vine Trail is an ongoing project of the Napa Valley Vine Coalition which has the stated goal of creating a 47 mile long bike trail along the entire length of Napa Valley. Currently 12.5 miles of trail is available between downtown Yountville and Kennedy Park in the city of Napa. Yo...
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