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Pleasanton, California

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

Top Chillin Spots in and near Pleasanton

  • Portola Valley, California

    Sunrise Hike at Windy Hill

    5.0
    There are a few options to this hike. Usually I would recommend parking in the lot on Portola Road, but because the preserve doesn't open until 30 minutes before sunrise, it's best to park up on Skyline Boulevard (Highway 35). There are two places to park up on Skyline, but the main parking lot i...
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  • Redwood City, California

    Hike or Bike the Old Growth Redwood Loop at El Corte de Madera

    4.4
    8.8 mi / 1900 ft gain
    This hike starts at the middle parking lot of the El Corte de Madera Open Space Preserve. The middle lot is located roughly a mile south on Skyline Boulevard from the Skeggs Point Vista. From the parking lot, take the Methuselah Trail for 0.3 miles until you reach the Timberview Trail. Take this ...
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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

    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 ...
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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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  • 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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  • 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

    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 ...
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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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  • Daly City, California

    Mussel Rock Loop

    4.0
    1.95 mi / 322 ft gain
    Mussel rock, a three-story, 50 million year old rock that has been carried some 500 miles northwest from Southern California, is where the San Andreas fault meets the Pacific Ocean. It's also an excellent spot to drink some wine and catch a sunset. From San Francisco, take Highway 1 south towar...
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  • Pacifica, California

    Picnic at Sharp Park Beach

    4.0
    A medium size beach with darker sand with big rocks and a paved path for walkers and joggers.  The beach is a great place to bring a picnic and watch the sunset.  It is located next to Pacifica Pier, which is popular for fishing.
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  • 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...
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  • Pacifica, California

    Fish at Pacifica Pier

    5.0
    This is a great place for fishing or just taking a walk to watch the sunset.  It's a great place to walk or jog, or even bring a pup!  There are lot of people fishing throughout the pier.   A short walk away is Sharp Park Beach, where you can relax and bring a picnic to watch the sunset.
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  • Half Moon Bay, California

    Hike Along the Half Moon Bay Coastal Trail

    4.6
    5 mi / 104 ft gain
    Start at the visitor center along Kelly Avenue. Take note that the day parking fee is $10 in 2016 for each vehicle. You will then be able to enjoy both the Coastside Trail and Francis Beach (plus other beaches) with access to the amenities such as coin-operated showers and a semi-private beach.Th...
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  • 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...
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