Cupertino, California
Looking for the best hiking in Cupertino? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Cupertino. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Cupertino
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Pescadero, California
Año Nuevo and Goat Trail Loop
4.03.76 mi / 761 ft gainThis steep and winding trail takes you to the top of a ridge where you can see the Pacific coastline and the redwoods piercing through the forest canopy. To do this trail connect the Ano Nuevo Trail, Olmo Fire Road, Goat Trail and the Six Bridges Trail. If you don't have all day to do the Canyon ...Read more -
Pescadero, California
Canyon Rim Route
5.08.94 mi / 2070 ft gainLocated 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...Read more -
Redwood City, California
Whittemore Gulch Trail
4.06.79 mi / 1791 ft gainThis trail starts out going downhill towards the ocean for the first half, which makes for a tough end to the hike as you trek back up the ridge. However, there are nice ocean and hilltop views that are worth the climb. On this trail, you'll pass 60+ banana slugs if conditions are right. They ar...Read more -
Redwood City, California
Whittemore Gulch and Harkins Ridge Loop Trail
4.66.43 mi / 1772 ft gainThere are two places to park for this specific loop- the main parking area on Highway 35 (Skyline Boulevard) and a smaller parking lot on the western end of the park. I would recommend parking at whichever is closest. Find directions to both on Openspace.org. From the main parking lot, the trail...Read more -
Redwood City, California
Whittemore Gulch and Purisima Creek Loop Trail
9.27 mi / 2165 ft gainThe Whittemore Gulch and Purisima Creek Loop Trail, nestled in the scenic Purisima Creek Redwoods Open Space Preserve near Redwood City, California, is a popular choice for hikers looking for a moderately challenging yet rewarding experience. This 9-mile loop trail winds through lush redwood fo...Read more -
Felton, California
Fall Creek Trail
5.07.21 mi / 1096 ft gainThis quiet 10 mile hike features a winding creek and tall redwoods throughout the trail. The parking at the Fall Creek Trailhead is limited, so it is best to get there before 10am. There are redwoods very close to the trail and a good portion is alongside the creek. Most of the trail is dirt, ...Read more -
Felton, California
Limestone Kilns and Big Ben Redwood Loop
5.08.37 mi / 1598 ft gainHenry Cowell Redwood State Park is a super easy destination to get to from Santa Cruz, but the seclusion of the Fall Creek Unit makes this a big bang for buck hike. This hike will take you to Big Ben, a medium sized old growth Redwood, and the abandoned Henry Cowell Lime and Cement Company Kilns ...Read more -
Felton, California
Redwood Grove Loop
4.00.93 mi / 144 ft gainHenry Cowell Redwoods State Park is located just a few miles north of the city of Santa Cruz, along Highway 9. The park is home to an array of hiking and biking trails, but the crown jewel of the park is the Redwood Grove Loop Trail, which is only a 1/4 mile in from the park's entrance. Many peo...Read more -
Felton, California
Observation Deck Loop in Henry Cowell Redwoods SP
4.35.3 mi / 869 ft gainThe trail starts at the Henry Cowell Redwoods State Park Visitors Center. Grab a map in the center, as your hike has you turning onto a few different trails to get to the observation deck. Starting at the Redwood Grove Loop Trail, follow the trail until it connects with the Pipeline Road Trail ...Read more -
Santa Cruz County, California
Camp at Henry Cowell Redwoods Campground
4.8/ 665 ft gainNestled in the Santa Cruz Mountains, Henry Cowell Redwoods State Park is a great weekend option for Bay Area residents. With approximately 30 miles of hiking trails, the incredible Garden of Eden swimming hole, and proximity to Santa Cruz - this campground is not to be missed! On sunny days, view...Read more -
Half Moon Bay, California
Purisima Creek Trail and Craig Britton Trail Loop
4.06.95 mi / 1411 ft gainThis hike is perfect for any time of year, always staying cool because it is near the coast, and there are multiple creeks that flow year-round. Even on foggy days, the fog condenses on trees to make it seem like it is "raining." Be warned that this hike has a lot of elevation change and is stre...Read more -
Half Moon Bay, California
Southern Beaches at San Gregorio State Beach
4.01.48 mi / 16 ft gainNot 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 ...Read more -
Morgan Hill, California
Uvas Canyon Waterfall Loop
4.01.48 mi / 463 ft gainUvas Canyon offers up to 6-miles of hiking trails, which includes a 1.5 mile loop, which runs along Swanson Creek and passes many of the park's waterfalls. To take short loop, head North out of the parking lot to the Swanson Creek Trail. Once you find Swanson Creek Trail, you'll be on the Waterfa...Read more -
Davenport, California
Greyhound Beach and Greyhound Rock
0.26 mi / 128 ft gainThe trailhead is at the Greyhound Rock State Marine Conservation Area which is directly off Highway 1. There is a large paved parking lot with a good amount of trees so finding a shady parking spot isn't that difficult (if that's important to you). The parking lot is located on the beach cliffs ...Read more -
San Mateo, California
Sugarloaf Mountain
5.01.64 mi / 417 ft gainSugarloaf is tucked away in Laurelwood Park which is located in a residential neighborhood right off of Hwy 92 in San Mateo, making this a great hiking & trail running option for Peninsula residents. I always park on Glendora Dr. and follow the paved path down towards the playground. At the ...Read more -
Santa Cruz, California
Rincon Fire Trail to San Lorenzo River
5.01.42 mi / 328 ft gainThe 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...Read more