Outbound Collective logo

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

  • 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. 
    Read more
  • 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...
    Read more
  • Kensington, California

    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...
    Read more
  • 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...
    Read more
  • 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 ...
    Read more
  • 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....
    Read more
  • 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...
    Read more
  • 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. 
    Read more
  • 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...
    Read more
  • 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 ...
    Read more
  • San Francisco, California

    Visit the Conservatory of Flowers

    4.7
    Spend a day exploring Golden Gate Park by jogging, cycling, or leisurely strolling.  There are so many fantastic stops in the park including a variety of lakes, playgrounds, a golf course, the California Academy of Science, the Conservatory of Flowers, and much much more!  It is definitely worth ...
    Read more
  • San Francisco, California

    Picnic Beneath the Golden Gate

    4.4
    If the weather forecast looks promising, you could do a lot worse than planning a picnic at the West Bluff Picnic Area in the Presidio. This area is south of Crissy Field (closer to the bridge) and before you get to Fort Point - situated perfectly to give you an amazing view of the Golden Gate, A...
    Read more
  • San Francisco, California

    Take in a Sunset on Marshall's Beach

    4.8
    If you're looking for one of the best views of the Golden Gate Bridge, Marshall's Beach gives you just that without the tourist crowds of Baker Beach.This small and hidden beach offers a narrow stretch of sand for those looking to throw a frisbee around or just hang out with friends. As it's tuck...
    Read more
  • Foster City, California

    Paddle the Foster City Lagoon

    The Foster City Lagoon is one of the most calm waters to paddle on.  This is a great spot for beginners to learn how to paddleboard for the first time. The lagoon gets very still and makes it the perfect spot for reflection photos.  On sunny days, there are many kayakers, SUP, small boats, and ev...
    Read more
  • 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...
    Read more
  • Sausalito, California

    Catch the Sunset at Swedes Beach

    This is a small tucked away beach in Sausalito, CA.  Being in the bay, it has very calm waters and is easy to swim in, though the water will be very cold.  There are pilings in the water that are remnants of the old piers.  It is a great beach to watch the sunset at. There is very limited street...
    Read more