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

  • 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...
    Read more
  • Yountville, California

    Bike the Napa Valley Wine Trail

    4.0
    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...
    Read more
  • Pescadero, California

    Pick Berries at Swanton's Berry Farm

    4.0
    Take a spectacularly scenic drive or bike ride out to this quaint coastal berry farm. Look out onto the shimmering ocean while you pick the ripest and sweetest berries yourself. Head inside their shop to enjoy pre-made jams, pies, chocolate covered strawberries, and so much more. While you're ins...
    Read more
  • Inverness, California

    Cypress Tree Tunnel in Point Reyes

    4.3
    Just north of San Francisco, there's a row of giant Monterey cypress trees that forms a “tree tunnel”. Loved by Bay Area locals, it's a tucked away spot in the Point Reyes National Seashore for photographers to capture early morning sun rays, or for anyone to get some moments of solitude. At the...
    Read more
  • Santa Rosa, California

    Crane Creek Canyon Loop

    4.3
    1.4 mi / 154 ft gain
    With multiple loops of varying length, this park is great for anyone looking for a casual hike around a beautiful area in the foothills of Rohnert Park. Crane Creek has nice secluded picnic areas next to the creek in the cover of willow, alder, buckeye and bay trees. There's also an 18-hole disc ...
    Read more
  • Inverness, California

    Point Reyes Lighthouse

    3.7
    1.26 mi / 292 ft gain
    From San Francisco, drive north over the Golden Gate Bridge and onto the scenic Route One. Plan to spend a full day on the round trip if you're going for the first time; along the drive, you'll most likely want to stop every ten minutes to check out the charming seaside towns or the stunning coas...
    Read more
  • Davenport, California

    Greyhound Beach and Greyhound Rock

    0.26 mi / 128 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 ...
    Read more