Woodside, California
With its stunning natural beauty and wide range of activities, Woodside, California is a great destination for those looking to explore the outdoors. Hiking, biking, fishing, kayaking, and more can be enjoyed in the area's many parks and trails, such as the Purisima Creek Trail, the Skyline-to-the-Sea Trail, and the Redwood Gulch Trail. For those looking to uncover the area's history, there are several historic sites including the Filoli Estate, the Woodside Store, and the Woodside Glens. Additionally, visitors can tour the area's wineries and breweries, such as the Woodside Vineyards and the Skyline Ridge Winery. With so much to explore, Woodside, California is a true outdoor paradise.
Top Spots in and near Woodside
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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 -
Redwood City, California
Stulsaft Park Loop
4.00.91 mi / 98 ft gainStulsaft Park Loop in Redwood City, California, is a scenic and family-friendly 0.9-mile loop trail, ideal for hiking, walking, and running. This is a relatively easy stroll with only 98 feet of elevation gain and is accessible for people of all fitness levels. This trail is also particularly pop...Read more -
Redwood City, California
Crystal Springs Trail Loop
4.05.4 mi / 1227 ft gainThis is a great hike for any season of the year, with rushing streams during the winter, wildflowers in the spring, and cool, shaded canyons during the summer. Starting from near the Zwierlein Picnic area, take the Crystal Springs to the left into the redwood forest. Stay straight at the next tr...Read more -
Redwood City, California
Old Growth Redwood Loop
4.45.68 mi / 1480 ft gainThis hike starts at the parking lot of the El Corte de Madera Open Space Preserve. The lot is located roughly a mile south on Skyline Boulevard from the Skeggs Point Vista. From the parking lot, take the Methuselah Trail for 0.3 miles until you reach the Timberview Trail. Take this trail for anot...Read more -
Emerald Hills, California
Sylvan Loop Trail
2.53 mi / 522 ft gainSylvan Loop Trail is a loop trail where you may see wildflowers located near Redwood City, California.Read more -
Emerald Hills, California
Edgewood Loop
4.03.29 mi / 607 ft gainEdgewood Park and Natural Preserve rests in San Mateo County, California. The sweeping hillsides exemplify the true native flora of California, as the foundation of rock and soil is poor in nutrients. Only a few specialized native plants are adapted to live here--don't miss the unique wildflower ...Read more -
Redwood City, California
Cordilleras & Dusty-Footed Woodrat Loop
3.73.83 mi / 676 ft gainGetting there: exit Highway 280 at Edgewood Road, travel .75 miles east, turn left on Crestview Drive, then immediately left again on Edmonds Road. Once parked, there are several different path options through the park. All of them connect in a large loop, and return to the parking lot. The Cord...Read more -
Redwood City, California
Hassler Loop Trail
4.01.48 mi / 289 ft gainExperience the natural beauty of the San Francisco Peninsula on the scenic Hassler Loop Trail, a 1.5-mile moderately challenging hiking trail nestled in Redwood City's Emerald Hills neighborhood. This beloved local trail offers hikers, nature enthusiasts, and outdoor adventurers a perfect blend...Read more -
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 -
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 -
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 -
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 -
Redwood City, California
Methuselah and El Corte De Madera Creek Loop
6.5 mi / 1778 ft gainThis loop hike will provide people with the opportunity to experience the tranquility of the lower canyons of the preserve, which tend to be more isolated than the heavier-trafficked trails that are closer to the main highway. Be warned that this hike is fairly strenuous because of the large amo...Read more -
Stanford, California
Stanford Dish Loop
4.43.67 mi / 472 ft gainIf you live in the Palo Alto area and are looking for a place to hike or run, The Dish is a close, and great way to get that exercise. Located right on the corner of Stanford Ave and Junipero Serra, you'll see that small gated entrance right when you drive on by. As far as parking goes, you're le...Read more
