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The Best Chillin in Oakland

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

  • Alameda, California

    Swim at Crown Memorial State Beach

    3.0
    This beach has some of the warmest ocean water in the bay area. The swimming area is also fairly shallow, making it a safer, more protected swimming area. Be sure to check the link below for updated water conditions, especially if it has rained recently. There is a bathhouse with changing rooms o...
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  • Oakland, California

    Hike Redwood Regional Park via the Dunn Loop

    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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  • Oakland, California

    Hike the Skyline Gate Staging Area

    4 mi / 692 ft gain
    The trail is lined with beautiful Redwoods and Eucalyptus Trees. There is lots of shade, but bring ample water just in case. Watch for roots and large rocks on the trail. The trail is generally well-maintained, but can get narrow in the winter. Dogs are allowed in Redwood Regional Park, but must ...
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  • Oakland, California

    Hike the Sequoia Bayview Trail

    2.9 mi / 429 ft gain
    Just outside of Oakland, this trail is easily accessible from anywhere in the Bay Area and has spectacular views of the Bay. This trail is good for all skill levels and is open year round. Dogs are allowed on this trail, but bring a leash! The trail meanders through several groves of Redwoods.  T...
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  • Oakland, California

    Hike the Huckleberry Nature Path Trail

    5.0
    2.3 mi / 561 ft gain
    The hike is shady in most parts. In the spring, wildflowers are abundant (as are Huckleberries and Manzanita). The trail is accessible year round, and is great for hikers, walkers, trail runners, and nature trips.  Start the loop from the Skyline Blvd staging area take the Huckleberry Loop. 
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  • Oakland, California

    Hike the Sibley Volcanic Trail

    3.8 mi / 757 ft gain
    The Sibley Volcanic Trail is a 3.8 mile loop that is great for all skill levels. The trail is best used from June - December, and is shared by kids, trail runners, mountain bikers, and hikers. Watch for wildlife and wildflowers.  There is little to no shade, so wear sunscreen and bring sun protec...
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  • Berkeley, California

    Swim at Lake Anza in Tilden Park

    5.0
    Lake Anza makes for a great warm weather swimming hole. The parking area is close to the beach along with the trail, which will take you around the lake. The beach gets plenty of sun and is fairly wind protected, which makes for a relaxing day. Bring some picnic food out to the lake and snag your...
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  • Moraga, California

    Hike the Rocky Ridge View, Sycamore, and Devil's Hole Trail

    6.3 mi / 2076 ft gain
    Turn right on Rocky Ridge Trail for .38 miles and turn left on Elderberry for 1.67 miles mostly through the woods. At the bottom where there are picnic tables, turn left for .37 back to the parking lot. The trail begins at the end of Bollinger Canyon Road at the Las Trampas Staging Area. Parking ...
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  • Kensington, California

    Visit the Tilden Little Farm

    4.0
    First make sure to stop at the store and stock up on fresh lettuce and celery for the animals. Your kids (or just the kid in you) will love to feed them! Note that they're only allowed to eat lettuce and celery, so don't try to feed them your own snacks or get creative. ;)If you want to make it a...
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  • San Francisco, California

    Catch a Sunrise at Ina Coolbrith Park

    5.0
    This tucked away neighborhood gem is less than a square block in size, but offers some of the best views of San Francisco. After a quick, but steep, 5 minute walk, you'll be rewarded with incredible views of: the city skyline, Coit Tower, Alcatraz, and the Bay Bridge. There are a few benches avai...
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  • San Francisco, California

    Park Day at Dolores Park

    3.8
    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

    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

    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

    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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  • 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

    Bike the Golden Gate to Sausalito

    4.7
    Riding your bike across the Golden Gate Bridge to Sausalito, and then enjoying some drinks on the back deck at Sam's, is a great way to spend a nice day. The views along the way are simply breathtaking. After your ride and a day of fun in Sausalito, you can return to San Francisco by ferry. It's ...
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