Outbound Collective logo

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

  • 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...
    Read more
  • Los Altos, California

    Park Day at Foothills Park

    1.7
    Disclaimer: Foothills Park requires proof of residence in Palo Alto or being accompanied by a resident of the city. Learn more here.Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After exiting you take a short scenic drive up the hill and come to the park entrance on your right...
    Read more
  • Paicines, California

    Hike the Old Pinnacle Trail in Pinnacles National Park

    5.0
    9 mi / 2000 ft gain
    Start at the Old Pinnacles Trailhead and embark on a roughly 9 mile long adventure surrounded by amazing geological rock formations and natural landscapes. Bask in the peace of nature... meander through meadows alongside the West Fork of Chalone Creek and into Old Pinnacles. Continuing on at the ...
    Read more
  • Paicines, California

    Hike to Bear Gulch Reservoir in Pinnacles National Park

    3.5
    1.5 mi / 275 ft gain
    Start the hike from the Bear Gulch Trail Parking lot.  While pulling in, the trail head is on the left.  The Trail is marked Reservoir, Caves, and High Peaks.  Continue down the trail until faced with a junction.  Make sure to admire rock formations while hiking!At the junction take the Bear Gulc...
    Read more
  • Soledad, California

    Explore Dreamy Wrath Wines Vineyards

    Just a short drive from some of the best trails and rock climbing at Pinnacles National Park, Wrath Wines' Soledad winery is a great way to wine'd down after a day of adventure.  What makes this grape growing region unique is the constant marine layer fog and wind stress out the grapes (that’s a ...
    Read more
  • Stanford, California

    Sunset Picnic at Kite Hill

    4.0
    Kite Hill is nothing more than what the name describes. A simple ascent less than 100 feet in elevation. But that 100 feet is all you need to feel like you discovered a little escape from the buzz below.To get there, you can park directly at the base of Kite Hill along Peter Coutts Rd and simply ...
    Read more
  • Carmel-by-the-Sea, California

    Soberanes Point

    1.82 mi / 295 ft gain
    Garrapata State Park is located along California's Highway 1, roughly 5 miles south of Carmel, California. The park is entirely free with multiple pull-outs and serves as one of the first grand views travelers encounter while heading south from the Monterey Peninsula to southern California. Garra...
    Read more
  • Carmel-by-the-Sea, California

    Secluded Beach Near Soberanes Point

    5.0
    0.2 mi / 40 ft gain
    When we stumbled upon this beach we were thrilled to have such great views with no crowds.  There is plenty of room to lay out in the sun, you can swim in the ocean to cool off, and the beach is surrounded by beautiful landscape.  If you decide to swim be very careful as the waves and currents ca...
    Read more
  • Loma Mar, California

    Bike Pescadero Creek County Park

    5.0
    12.5 mi / 1350 ft gain
    Pescadero Creek County Park and the connected Sam McDonald and Memorial Park are located deep in the Santa Cruz Mountains holding a vast network of secluded trails. From biking to backpacking, this area is a perfect place for a day or weekend adventure. This area also has the added bonus having r...
    Read more
  • Loma Mar, California

    Camp Under the Redwoods at Memorial Park

    With old growth redwoods and a creek swimming area, Memorial Park is a perfect escape from the hustle and bustle of the Bay Area. Memorial Park is only a few miles east of the town of Pescadero. To get here, you can either approach from Highway 1 and drive up Pescadero Creek Road or take Highway ...
    Read more
  • Pescadero, United States

    Relax at Costanoa Lodge

    3.0
    Looking for a quick escape from the city, but sleeping on the ground isn’t really your thing? Look no further than Costanoa Lodge in Pescadero, an upscale "glamping" experience just an hour south of San Francisco with tons of hiking options. This is a really fun option for anyone who enjoys being...
    Read more
  • Carmel-by-the-Sea, California

    Calla Lily Valley

    4.5
    0.31 mi / 46 ft gain
    Parking for Calla Lily Valley is available along the dirt pullout at Gate 19 for Garrapata State Park, near mile-marker 63. Signs are small and difficult to see. Follow the path between the guide wires and take the right fork, heading north to the bluff overlooking the beach. Continue north and f...
    Read more
  • Pescadero, California

    Hike the Canyon Rim Route in Butano State Park

    5.0
    11.7 mi
    Located deep within the Santa Cruz Mountains, Butano State Park boasts a large redwood canyon with many miles of hiking trails as well as campsites. This state park is one of the quietest and least visited parks on the peninsula making a perfect place to escape the hustle of the Bay Area Butano S...
    Read more
  • Carmel-by-the-Sea, California

    Garrapata Beach

    4.6
    A wonderful roadside beach and state park. Easy parking on both sides of Hwy. 1 with short access trails. There are almost 2 miles of coastline trails heading north and south from the parking area. The north end of the beach is great for swimming and surfing when the sea is calm and the south ...
    Read more
  • 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...
    Read more
  • Pescadero, California

    Explore the Pidgeon 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 hand...
    Read more