Pleasanton, California
Looking for the best chillin in Pleasanton? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pleasanton. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Pleasanton
-
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
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 -
San Francisco, California
Ina Coolbrith Park
5.0This tucked away neighborhood gem is less than a square block in size, but offers some of the best views of San Francisco. After a quick, but steep, 5 minute walk, you'll be rewarded with incredible views of: the city skyline, Coit Tower, Alcatraz, and the Bay Bridge. There are a few benches avai...Read more -
San Francisco, California
Dolores Park
4.1Mission Dolores Park spans two city blocks in San Francisco's Mission District, offering 16 acres of recreational space with stunning city skyline views. This historic park, established in 1905, serves as a cultural hub and outdoor gathering space for both locals and tourists. Location & A...Read more -
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 -
San Francisco, California
Billy Goat Hill
4.0Billy Goat Hill Park is located in the Glen Park neighborhood of San Francisco. The park has street parking at the top of the park on Beacon Street or at the base of the park on Ladley Street. Getting to the swing is only a short walk up or down the stairs that run through the middle of the park....Read more -
San Francisco, California
Seward Street Slides
4.2Tucked away in a small neighborhood park in Eureka Valley is a set of really fun, slippery, and surprisingly steep concrete slides. They were originally designed by a 14 year old kid over 30 years ago, and we all owe him a big hat tip. People use a variety of sliding materials (saucers, food tray...Read more -
San Francisco, California
Twin Peaks
4.6Most locals have heard of Twin Peaks, so if you hop in an Uber or Taxi you should be just fine. If not or you are driving yourself, head for Twin Peaks Boulevard, then just follow it to the top. Voila! When you're there, be sure to catch a sunset, as it is absolutely breath-taking, If you are lu...Read more -
San Francisco, California
The Wave Organ
The Wave Organ is an acoustic sculpture located on a jetty in the Marina district of San Francisco. Designed by Peter Richards and built in collaboration with sculptor George Gonzalez, this unique attraction was completed in 1986. It utilizes the natural movement of the waves to create a variety ...Read more -
San Francisco, California
Conservatory of Flowers
4.7Spend a day exploring Golden Gate Park by jogging, cycling, or leisurely strolling. There are so many fantastic stops in the park including a variety of lakes, playgrounds, a golf course, the California Academy of Science, the Conservatory of Flowers, and much much more! It is definitely worth ...Read more -
Daly City, California
Mussel Rock Loop
4.01.95 mi / 322 ft gainMussel rock, a three-story, 50 million year old rock that has been carried some 500 miles northwest from Southern California, is where the San Andreas fault meets the Pacific Ocean. It's also an excellent spot to drink some wine and catch a sunset. From San Francisco, take Highway 1 south towar...Read more -
Pacifica, California
Picnic at Sharp Park Beach
4.0A medium size beach with darker sand with big rocks and a paved path for walkers and joggers. The beach is a great place to bring a picnic and watch the sunset. It is located next to Pacifica Pier, which is popular for fishing.Read more -
San Francisco, California
Sunset Reservoir
0.69 mi / 62.99 ft gainHidden in the Sunset District, the Sunset Reservoir is more than just piece of city infrastructure — its surrounding paths make for a convenient urban stroll with peaceful views, a solar rooftop, and surprising vistas of San Francisco. Trail & Walk Details Many local walkers estimate the fu...Read more -
San Francisco, California
Picnic Beneath the Golden Gate
4.7If the weather forecast looks promising, you could do a lot worse than planning a picnic at the West Bluff Picnic Area in the Presidio. This area is south of Crissy Field (closer to the bridge) and before you get to Fort Point - situated perfectly to give you an amazing view of the Golden Gate, A...Read more -
Pacifica, California
Fish at Pacifica Pier
5.0This is a great place for fishing or just taking a walk to watch the sunset. It's a great place to walk or jog, or even bring a pup! There are lot of people fishing throughout the pier. A short walk away is Sharp Park Beach, where you can relax and bring a picnic to watch the sunset.Read more -
Half Moon Bay, California
Half Moon Bay Coastal Trail
4.65.51 mi / 220 ft gainStart at the visitor center along Kelly Avenue. Take note that the day parking fee is $10 in 2024 for each vehicle. You will then be able to enjoy both the Coastside Trail and Francis Beach (plus other beaches) with access to the amenities such as coin-operated showers and a semi-private beach. ...Read more