Cupertino, California
Looking for the best running 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 Running Spots in and near Cupertino
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Half Moon Bay, California
Gray Whale Cove Trail
4.52.23 mi / 367 ft gainGray whale cove trail is a splendid, short, and easy hike for the entire family with beautiful ocean views. The starting point is conveniently located near a parking lot that accesses Montara State Beach. From the south end of the parking lot, follow the trail up through the coastal scrub. Within...Read more -
Half Moon Bay, California
Montara Mountain North & Middle Peaks Loop
4.37.22 mi / 1929 ft gainNOTE: as of 2019, North Peak has been fenced off around the installation of a radio tower and weather station. Additionally, the summit has been found to be a habitat for the endangered San Bruno elfin butterfly. The Gray Whale Cove State Beach is a popular seaside trail that’s just 20 minutes s...Read more -
Pacifica, California
Mori Point Loop
4.82.54 mi / 276 ft gainStart at the parking lots close to the pier, where bathrooms are also available. Walk along the pier to watch the sunset as it begins. Next, walk along Sharp Park Beach to discover the plethora of wild flowers and friendly locals always ready to guide you on your walk. Take the stairs up to the...Read more -
Pacifica, California
Milagra Overlook Trail
5.02.51 mi / 558 ft gainFound this hike with some friends after spending some time googling in my car when we were in the area looking for a quick hike with a view! Dog friendly Free parking (but quite limited) Ocean views Known to have gorgeous wildflower blooms (we were not there during this)Porta-potty type toilet...Read more -
Oakland, California
Run the Circumnavigation of Redwood Regional Park's Ultimate Trail Loop
5.07.5 mi / 1600 ft gainIt’s difficult to have a car in San Francisco, but oh-so worth it when it comes to weekend getaways, especially with all the Bay Area has to offer. This is a super accessible trail system just 30 minutes outside of the city that makes for a fun, easy trail run or hike.Redwood Regional Park, part ...Read more -
San Francisco, California
Bayview Hill Loop
4.01.24 mi / 184 ft gainBayview Hill Loop is a loop trail that starts with a paved uphill climb and views of the bay facing toward the East Bay located in the Bayview neighborhood of San Francisco, California.Read more -
Moraga, California
Bollinger Creek Loop Trail
1.43 mi / 213 ft gainLas Trampas Regional Wilderness offers an extensive trail system for hikers, horseback riders and mountain bikers. The trail is open year round and dogs are allowed. The Las Trampas and Bollinger faults spread apart to reveal a wonderful wilderness area with ancient remnants of beaches. The entir...Read more -
Oakland, California
Hike Redwood Regional Park via the Dunn Loop
5.03.6 mi / 606 ft gainThe 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.Read more -
Oakland, California
East & West Ridge Loop
4.53.47 mi / 833 ft gainTucked away in the hills of Oakland, you will find one of the homes of California's Coastal Redwoods. Created by a unique geographical circumstance, this forest breathes winds funneled through the Golden Gate across the bay, which created environment opportune for Redwood growth. These Redwoods a...Read more -
Livermore, California
Condor, Volvan, Stone Corral, Coyote Loop
4.54.38 mi / 620 ft gainThis regional preserve is perfect for day hikes. There are also designated campsites and even a backpack campsite. Horses and dogs are welcome in the preserve. There are many different clearly marked trails that one can choose from. A good 4.5 mile loop is to start at the Park Residence entrance...Read more -
San Francisco, California
Lake Merced Loop
4.74.53 mi / 180 ft gainLake Merced Loop is a loop trail in the southwestern part of San Francisco. This trail is used for running and walking. You'll see plenty of people getting exercise or taking their dog for a stroll. There are also benches and tables around the loop. The lake itself is fresh water and is used for...Read more -
San Francisco, California
Glen Canyon Park Trail
5.01.76 mi / 394 ft gainGlen Canyon Park Trail is a loop most commonly used for running or hiking in the southwestern side of San Francisco, California. Parking for the loop is street parking, so be sure to take any valuables out of the car with you. Note: There are restrooms available at the Glen Canyon Recreation Ce...Read more -
Danville, California
Summit Mount Diablo via Rock City Trail
5.07.8 mi / 2299 ft gainAlthough steep in sections, this trail is a wonderful workout and hikers are more than rewarded for their efforts. The Rock City Trail is a direct route to the summit of Mount Diablo, and the park is an ecological treasure dear to the hearts of Bay Area residents. The best views are on clear days...Read more -
Danville, California
Hike in Mount Diablo's Madrone Canyon
2.8 mi / 550 ft gainThis hike starts at the Rock City area of Mount Diablo State Park. Begin at the Madrone Canyon Trail, hiking southeast towards the Devils Slide trail. Along this section of the hike, the trail dips into a wooded canyon and follows the path of a small creek. To best experience the beauty of the cr...Read more -
San Francisco, California
Mount Davidson
4.51.03 mi / 299 ft gainMount Davidson Park is located in the southwestern part of the city nestled between Diamond Heights and Portola Dr. The climb isn't too difficult, but to reach the top of the 928ft summit, you should wear close-toed shoes and be ready for some loose gravel or mud if it's been raining. The hike is...Read more -
San Francisco, California
Fort Funston Trail
4.71.81 mi / 253 ft gainFort Funston is an SF gem I discovered when looking for a dog friendly hike near the city. Located west of Lake Merced, you'll find a gorgeous Northern California beach oasis where you and your dog can run wild and free :). Parking is located at the top of the park where you'll descend a steep se...Read more