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Woodside, California

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

Top Chillin Spots in and near Woodside

  • Santa Cruz, California

    Hike the Rincon Fire Trail

    5.0
    1 mi / 300 ft gain
    The Rincon Fire Trail Starts at a small dirt parking lot next to CA-9 and traverses down the mountain to the San Lorenzo River Connecting with the Pipeline Trail. The trail can be a simple one of a mile out and back or up to 5 miles depending on your preference. The elevation will change by about...
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  • Mill Valley, California

    Explore WWII Ruins on Point Bonita

    4.3
    0.25 mi / 200 ft gain
    All throughout the Marin Headlands are WWII-era bunkers, batteries and ruins, including a complex on the hillside above the Point Bonita Lighthouse that provide amazing views of San Francisco, the Golden Gate, and the north coast.Drive out to the parking lot for the Point Bonita Lighthouse in the...
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  • 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...
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  • Berkeley, California

    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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  • Livermore, California

    Del Valle Regional Park

    4.0
    Looking for a quick summer escape filled with stand up paddling, canoeing, fishing, hiking, and picnics? Look no further than Del Valle Regional Park. Consistently considered one of the best campgrounds in the Bay Area, the centerpiece of Del Valle is a 5-mile long lake that allows swimming, fish...
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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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  • 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...
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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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  • Muir Beach, California

    Bonfire at Muir Beach

    5.0
    Take in a scenic sunset and enjoy the warmth of a bonfire on the beach! Muir Beach changes the number of fire pits it has seasonally. May through November, the beach offers 6 fire pits, and in the colder months (December through April), there are 3 fire pits on the beach toward the south end of t...
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  • Santa Cruz, California

    Surf at Natural Bridges State Beach

    4.5
    Natural Bridges is off of West Cliff Drive to the north of popular Santa Cruz break, Steamer Lane. The break is a right point break, which breaks on a rocky shelf and reef. The break is best during sizable swells (NW, SW, and West) and a low tide. Be sure to check the wind, this break gets blown ...
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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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  • Santa Cruz, California

    Bonfire at Seabright State Beach

    5.0
    This is a wide, beautiful beach that's an amazing spot to spend the day and enjoy a bonfire at night. Seabright is probably the most popular spot in Santa Cruz for a bonfire, due to its convenient proximity to the Beach Boardwalk. But luckily, this beach is tucked in between the San Lorenzo River...
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  • Santa Cruz, California

    A Beach Bonfire in Santa Cruz at Twin Lakes SB

    This one-mile stretch of beach is the perfect option for those looking for a peaceful Santa Cruz experience, but without the crowds. The beach features soft sand, playful surf, an awesome view of Walton Lighthouse, and a handful of fire pits to choose from. It's a great spot to spend the entire d...
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  • Santa Cruz, California

    Beach Day at Lighthouse Field State Beach

    4.0
    This beach is less crowded compared to other beaches in Santa Cruz.  I got there early on a Saturday and found easy street parking.  There was plenty of space to spread out on the soft sand.  Later in the day I saw dolphins several times!  This is close to the Santa Cruz Surfing Museum.  It’s als...
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  • Tiburon, California

    Bouldering at Ring Mountain

    0.5 mi / 400 ft gain
    Itching to climb outdoors near San Francisco?  With only a quick drive from the city, Ring Mountain is a beautiful nature preserve overlooking the city of San Francisco offering two main rock formations, Turtle Rock (Pictured) and Split Rock.  Split Rock is the slabby rock south of the parking ar...
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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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