San Mateo County, California
Looking for the best chillin in San Mateo County? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around San Mateo County. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near San Mateo County
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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 -
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 -
Portola Valley, California
Sunrise Hike at Windy Hill
5.0There are a few options to this hike. 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, but the main parking lot i...Read more -
Half Moon Bay, California
Stroll along the Southern Beaches at San Gregorio State Beach
4.02.9 mi / 413 ft gainNot a trail per se, but approximately 3 miles (down and back) of beautiful beach to walk down. Lots of interesting caves, wild animals, and rock formations to discover. This is a popular location for sea kayakers. San Gregorio State Beach was originally founded to protect the estuary at the back ...Read more -
Redwood City, California
Hike or Bike the Old Growth Redwood Loop at El Corte de Madera
4.48.8 mi / 1900 ft gainThis hike starts at the middle parking lot of the El Corte de Madera Open Space Preserve. The middle 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 ...Read more -
Half Moon Bay, California
Watch the Sunset at Martin's Beach
4.5Martin's Beach is a beach about 7 miles south of Half Moon Bay. It features a large, very cool looking rock formation right off the coast. This beach is accessible via Martin's Beach Road, which is a small turn off on your right when southbound on Highway 1, though sometimes the road is only open...Read more -
Los Altos, California
Park Day at Foothills Park
1.7Disclaimer: Foothills Park requires proof of residence in Palo Alto or being accompanied by a resident of the city. Learn more here.Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After exiting you take a short scenic drive up the hill and come to the park entrance on your right...Read more -
Pescadero, California
Hike the Canyon Rim Route in Butano State Park
5.011.7 miLocated deep within the Santa Cruz Mountains, Butano State Park boasts a large redwood canyon with many miles of hiking trails as well as campsites. This state park is one of the quietest and least visited parks on the peninsula making a perfect place to escape the hustle of the Bay Area Butano S...Read more -
Pescadero, California
Catch a Sunset at Bean Hollow State Beach
5.0There are a bunch of places to photograph this beach if you head north on the trail that runs along the beach.There is parking at the beach but it can fill up quickly!The only warning you need is about the tide. Make sure you are watching it the entire time because it can creep up on you and will...Read more -
Cowell Ranch Beach Access, California
Picnic at Cowell Ranch Beach
5.0Hike half a mile to this beautiful, secluded beach. There are high cliffs with a steep staircase down to the beach. The beach has wonderful rock formations on one side. It is a great place to watch the sunset or bring a picnic. A great place for a beach day if you are looking for something le...Read more -
Half Moon Bay, California
Bike the Cowell-Purisima Coastal Trail
4.0This trail begins at the Cowell State Beach parking lot and is only open on the weekends. From the lot, take the short Cowell Ranch Access trail to a scenic overlook. There are steps down to the secluded pocket beach just above the main trail. The trail playfully meanders along the cliffside with...Read more -
Stanford, California
Sunset Picnic at Kite Hill
4.0Kite Hill is nothing more than what the name describes. A simple ascent less than 100 feet in elevation. But that 100 feet is all you need to feel like you discovered a little escape from the buzz below.To get there, you can park directly at the base of Kite Hill along Peter Coutts Rd and simply ...Read more -
Pescadero, California
Explore the Pidgeon Point Lighthouse
5.0Pidgeon Point Lighthouse is conveniently located just 50 miles south of San Francisco. Constructed in 1872 and standing at 115 feet, it is among the tallest lighthouse in America.Part of the state park system, it is surprisingly secluded. Numerous parking space were available in the lot with hand...Read more -
Pescadero, California
Exploring Big Sur to Pigeon Point
We started off in Big Sur and took as many pull-off viewpoints as possible between Big Sur and the final destination, Pigeon Point Lighthouse. The weather was foggy in some spots but would open up to reveal the vast Pacific Ocean and sun in others. The weather was mild for us but we're familiar w...Read more -
Pescadero, United States
Relax at Costanoa Lodge
3.0Looking for a quick escape from the city, but sleeping on the ground isn’t really your thing? Look no further than Costanoa Lodge in Pescadero, an upscale "glamping" experience just an hour south of San Francisco with tons of hiking options. This is a really fun option for anyone who enjoys being...Read more -
Half Moon Bay, California
Hike Along the Half Moon Bay Coastal Trail
4.65 mi / 104 ft gainStart at the visitor center along Kelly Avenue. Take note that the day parking fee is $10 in 2016 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.Th...Read more