San Mateo, California

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

Top Chillin Spots in and near San Mateo

  • Portola Valley, California

    Windy Hill: Spring Ridge, Anniversary Loop

    5.0
    6.18 mi / 1421 ft gain
    There are a few options to hiking Windy Hill Open Space Preserve. 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...
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  • San Francisco, California

    Billy Goat Hill

    4.0
    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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  • 3160 North Shoreline Boulevard, California

    SUP Shoreline Lake

    4.0
    Shoreline Lake features a big lake, many hiking and biking trails, and lot of picnic areas in Mountain View, CA. Kayaks, SUP, and various boats can be rented from the boat house. This is a great place to enjoy the water no matter what season it is. There are large grassy areas for kids to run and...
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  • San Francisco, California

    Dolores Park

    4.1
    Mission Dolores Park spans two city blocks in San Francisco's Mission District, offering 16 acres of recreational space with stunning city skyline views. This historic park, established in 1905, serves as a cultural hub and outdoor gathering space for both locals and tourists. Location & A...
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  • San Francisco, California

    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 lu...
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  • Los Altos, California

    Foothills Park: Boronda Lake

    3.0
    0.93 mi / 0 ft gain
    Situated in the hills above Palo Alto; Foothills Park is the perfect spot to spend the day outdoors. With hiking, fishing, picnic areas, wide open fields, and expansive views of the Bay Area, this hidden gem is a must visit. Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After ...
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  • San Francisco, California

    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

    Sunset Reservoir

    0.69 mi / 62.99 ft gain
    Hidden in the Sunset District, the Sunset Reservoir is more than just piece of city infrastructure — its surrounding paths make for a convenient urban stroll with peaceful views, a solar rooftop, and surprising vistas of San Francisco. Trail & Walk Details Many local walkers estimate the fu...
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  • Half Moon Bay, California

    Southern Beaches at San Gregorio State Beach

    4.0
    1.48 mi / 16 ft gain
    Not a trail per se, but approximately 3 miles (down and back) of beautiful beach to walk down. Lots of interesting caves, wild animals, and rock formations to discover. This is a popular location for sea kayakers. San Gregorio State Beach was originally founded to protect the estuary at the back ...
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  • San Francisco, California

    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

    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

    Beach Bonfire at Ocean Beach

    4.3
    Yes, it's often cold in the city. So, what's the best way to warm up? Bring some blankets, a jacket or two, and come out to Ocean Beach to enjoy a bonfire, a sunset, and some quality time with friends. The fire pits are between Fulton and Lincoln. On a sunny day, get there early if you want to ge...
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  • Oakland, California

    Dunn Loop

    5.0
    3.08 mi / 758 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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  • San Francisco, California

    The Wave Organ

    The Wave Organ is an acoustic sculpture located on a jetty in the Marina district of San Francisco. Designed by Peter Richards and built in collaboration with sculptor George Gonzalez, this unique attraction was completed in 1986. It utilizes the natural movement of the waves to create a variety ...
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  • San Francisco, California

    Sutro Baths Ruins

    4.5
    0.46 mi / 115 ft gain
    Whether you simply look down on the ruins from the [conveniently located] parking lot above, or choose to walk down the stairs and explore, you will be greeted with stunning views of the Baths, and the Pacific Ocean stretching infinitely beyond. The highlight of any trip to the Sutro Baths is ...
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  • San Francisco, California

    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 tu...
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