Gilroy, California

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

Top Chillin Spots in and near Gilroy

  • 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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  • Pescadero, California

    Exploring Big Sur to Pigeon Point

    We started off in Big Sur and took as many pull-off viewpoints as possible between Big Sur and the final destination, Pigeon Point Lighthouse. The weather was foggy in some spots but would open up to reveal the vast Pacific Ocean and sun in others. The weather was mild for us but we're familiar w...
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  • Pescadero, California

    Pigeon Point Lighthouse

    5.0
    Pidgeon Point Lighthouse is conveniently located just 50 miles south of San Francisco. Constructed in 1872 and standing at 115 feet, it is among the tallest lighthouse in America. Part of the state park system, it is surprisingly secluded. Numerous parking space were available in the lot with ha...
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  • Pescadero, California

    Bean Hollow State Beach

    5.0
    There are a bunch of places to photograph this beach if you head north on the trail that runs along the beach. There is parking at the beach but it can fill up quickly! The only warning you need is about the tide. Make sure you are watching it the entire time because it can creep up on you and ...
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  • Redwood City, California

    Old Growth Redwood Loop

    4.4
    5.68 mi / 1480 ft gain
    This hike starts at the parking lot of the El Corte de Madera Open Space Preserve. The 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 trail for anot...
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