Pleasanton, California
Pleasanton, California is home to some of the best outdoor activities and attractions. From scenic trails to outdoor adventures, there's something for everyone. Must-visit attractions include the Pleasanton Ridge Regional Park, Shadow Cliffs Regional Recreation Area, and the Pleasanton Golf Center. For the best trails and activities, head to the Pleasanton Ridge Regional Park for a hike or bike ride. Shadow Cliffs Regional Recreation Area is great for fishing, swimming, and picnicking. Pleasanton Golf Center is a great spot for golfers of all levels. Whether you're looking for a peaceful day outdoors or an exciting experience, Pleasanton has it all.
Top Spots in and near Pleasanton
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Portola Valley, California
Windy Hill Loop
4.37.48 mi / 1578 ft gainThis 7.2-mile loop starts by heading out of the parking lot and onto the Spring Ridge Trail. Head Southeast On Spring Ridge Trail until you connect with Hamms Gulch Trail. When you jump on Hamms Gulch, head southwest for ~3.4 miles as you circle the far end of the OSP. At this point, you will con...Read more -
San Francisco, California
San Francisco Crosstown Trail
5.016.71 mi / 1975 ft gainThe San Francisco Crosstown Trail runs point-to-point from Candlestick Point to Land End. The SF Crosstown Trail officially opened in 2014. It connects park trails to neighborhoods and communities. In it's in entirety it's almost 17 miles long with 5 Sections available for those looking to bre...Read more -
Saratoga, California
Seven Springs Trail Loop
2.75 mi / 541 ft gainThe Seven Springs loop is only one great option of several in the preserve. Starting from the Prospect Rd parking lot the loop is 2.8 miles of rolling hills in and out of the shade. Most of the trail is at least 2 person width so easy to walk with a friend or furry companion. There have been larg...Read more -
San Mateo County, California
Sawyer Camp Trail
5.011.61 mi / 1152 ft gainThe Sawyer Camp Trail is a popular paved trail that stretches alongside the Crystal Springs Reservoir all the way to Hillcrest Blvd. The sixth mile crosses over the San Andreas Dam with nice views of San Andreas Lake. There are markers every half mile which makes timing and tracking your run eas...Read more -
Los Altos, California
Stevens Creek & Canyon Loop
4.52.77 mi / 446 ft gainThis hike is best done in the late fall, winter, and spring so that the creek is running and the hills are green. Starting at the preserve parking lot, the first half of the hike is predominantly downhill. At the main trailhead, start in the direction of the Stevens Creek Nature Trail, as told by...Read more -
Los Altos, California
Black Mountain and Stevens Creek Canyon
4.05.47 mi / 1066 ft gainThis hike can be done during any season, but for the creek to be running and for more comfortable temperatures, it is best to go on a cool winter or spring day. Starting at the preserve parking lot, take the Stevens Creek nature trail, allowing you to witness spectacular views of a large, forest...Read more -
San Francisco, California
Bayview Hill Loop
4.51.24 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 -
Burlingame, California
Mills Canyon Nature Area Trail Loop
4.01.45 mi / 331 ft gainNestled within Burlingame, California, the Mills Canyon Nature Area Trail Loop offers hikers a serene escape into nature. This approximately 1.5-mile loop meanders through diverse landscapes, including mixed woodlands and grasslands, providing opportunities for birdwatching and enjoying native ...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 -
San Francisco, California
Paddle at Crane Cove
5.0Crane Cove is a beautiful waterfront park with access for paddle boards and kayaks. This area is protected from the wind (it will be less choppy here than in the middle of the bay). If you decide to paddle up to mission bay or down towards Islais Creek you'll most likely face more currents and w...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 -
Burlingame, California
Ed Taylor Loop Trail
4.01.42 mi / 295 ft gainThis hike can be done at any time of year. Hiking in winter and spring means that many varieties of wildflowers will be present, and the creek will have much more water. Summer and fall mean higher temperatures and drier conditions, but the hike is still a pleasant experience. Begin the hike at ...Read more -
La Honda, California
Sunny Jim and Christmas Tree Trails
4.02.99 mi / 531 ft gainThere are a bunch of beginner to intermediate mountain biking trails at Skyline Ridge Open Space Preserve (click here for a trail map). There are some beginner mountain biking classes that come here to learn. There is a Christmas tree farm that usually has small Christmas trees growing. On a r...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
