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
-
San Jose, California
Senador Mine & Guadalupe Loop
4.34.83 mi / 863 ft gainThe 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 bi...Read more -
La Honda, California
Portola Redwoods State Park Loop
4.88.21 mi / 1924.54 ft gainTake in the best of Portola Redwoods State Park: towering redwoods, a waterfall, wildflowers, and a mix of narrow singletrack and wide old logging roads. This loop comes in around 8 miles, with a shorter 5-mile option if you’re looking for something more mellow. Redwood hikes are always a trea...Read more -
La Honda, California
Brook Trail Loop
7.63 mi / 1457 ft gainThe Brook Trail Loop is a beautiful hike, starting off in Sam McDonald County Park and later entering into Pescadero Creek County Park. This adventure can be done in any season, with the trails almost entirely shaded for even the hottest summer days. Starting off from the Heritage Grove trailhea...Read more -
Portola Valley, California
Windy Hill: Spring Ridge, Anniversary Loop
5.06.18 mi / 1421 ft gainThere 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...Read more -
Portola Valley, California
Windy Hill via Anniversary Trail Loop
0.89 mi / 164 ft gainTo get a good viewing point for the sunrise, take a quick on the Anniversary Trail up to Windy Hill. This is a real bang-for-your-buck adventure as the trail isn't too long and you get to see a spectacular sunrise combined with great views of both the Bay Area and out towards the ocean. Note tha...Read more -
La Honda, California
Sam McDonald Park Loop
5.012.19 mi / 2192 ft gainThe Pescadero Creek Park Complex is a great place to escape for a day or overnight hike in the heart of the Bay Area. You will need to get a permit to stay overnight - these can be attained on a first-come, first-serve basis from the ranger station. Most of the campsites here are also available f...Read more -
San Jose, California
North Rim Trail to Eagle Rock
5.01.94 mi / 240 ft gainNorth Rim Trail to Eagle Rock is an out-and-back trail that takes you past scenic surroundings located near San Jose, California.Read more -
Woodside, California
Meadow & Bear Gulch Loop
5.04.57 mi / 1089 ft gainLocated in the iconic Silicon Valley town of Woodside, Wunderlich County Park offers a number of hiking trails as well as some horseback riding trails through the wilderness. Once in the parking lot, you will see a number of stables, riding ring, as well as a beautiful historic stable that was ...Read more -
Fremont, California
Mission Peak via Hidden Valley Trail
4.26.16 mi / 2116 ft gainBreathtaking views of the Bay Area are your reward for making this climb to the top of Mission Peak. It’s a 3-mile trek to the top of the peak and then back down the same way. This is a moderate hike that provides a nice workout – so be prepared. Park at the Stanford Avenue entrance gate. There ...Read more -
Loma Mar, California
Bike Pescadero Creek County Park
5.012.5 mi / 1350 ft gainPescadero 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 -
Boulder Creek, California
Berry Creek Falls Loop (Closed)
4.810 mi / 2310 ft gainUnfortunately, this trail is closed due to a past fire. See CA.Gov for updates on trails in Big Basin. Nestled in California's oldest state park, the popular Berry Creek Falls Loop hike begins at the Big Basin park headquarters. If you're up for 11 miles, a thousand feet of elevation gain throu...Read more -
Boulder Creek, California
Hike the Ocean View Summit Loop
4.06 mi / 600 ft gainThis hike begins at the Big Basin park headquarters. If you're up for 6 miles through giant redwoods and along serene creeks, and with an ocean view, then this is the hike for you. Ocean view summit loop starts on the Gazos Creek Road bridge, next turn right on to the Middle Ridge Fire Road, whic...Read more -
Boulder Creek, California
Camp at Big Basin Redwoods State Park
4.00.5 miBig Basin is currently closed including the campgrounds. Please visit the Parks.ca.gov site for updated details. An hour away from the thrumming city of San Jose, ancient immense trees live in a forest full of vibrant ferns and rushing waterfalls. Big Basin Redwoods State Park encompasses 10,00...Read more -
Boulder Creek, California
Hike the Old Growth Redwoods Trail
4.50.5 miQuick half-mile stroll through the old growth Redwoods that will show you the nature of the ever-living redwood tree.Redwoods are capable of withstanding storms, floods, fire, droughts, and even termites. These legendary trees can live for over 2,000 years and possess incredible strength, vigor, ...Read more -
Boulder Creek, California
Big Basin's Sunset Trail Camp
4.89.46 mi / 2146 ft gainThis trail and campsite is currently closed (learn more). Looking for a more authentic hiking and camping weekend, without having to drive hours away to find it? Then the Sunset Trail Camp within Big Basin Redwoods SP is your ticket. To access this site, you'll need to hike the famous Skyline-to...Read more