Redwood City, California
Looking for the best chillin in Redwood City? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Redwood City. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Redwood City
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Foster City, California
Paddle the Foster City Lagoon
5.0The Foster City Lagoon is one of the most calm waters to paddle on. This is a great spot for beginners to learn how to paddleboard for the first time. The lagoon gets very still and makes it the perfect spot for reflection photos. On sunny days, there are many kayakers, SUP, small boats, and ev...Read more -
San Mateo, California
Sugarloaf Mountain
5.01.64 mi / 417 ft gainSugarloaf is tucked away in Laurelwood Park which is located in a residential neighborhood right off of Hwy 92 in San Mateo, making this a great hiking & trail running option for Peninsula residents. I always park on Glendora Dr. and follow the paved path down towards the playground. At the ...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 -
Stanford, California
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 simpl...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 -
3160 North Shoreline Boulevard, California
SUP Shoreline Lake
4.0Shoreline Lake features a big lake, many hiking and biking trails, and lot of picnic areas in Mountain View, CA. Kayaks, SUP, and various boats can be rented from the boat house. This is a great place to enjoy the water no matter what season it is. There are large grassy areas for kids to run and...Read more -
Los Altos, California
Foothills Park: Boronda Lake
3.00.93 mi / 0 ft gainSituated in the hills above Palo Alto; Foothills Park is the perfect spot to spend the day outdoors. With hiking, fishing, picnic areas, wide open fields, and expansive views of the Bay Area, this hidden gem is a must visit. Foothills Park is 2.7 miles west of 280 after exiting Page Mill. After ...Read more -
Cowell Ranch Beach Access, California
Cowell Ranch Beach
5.01.14 mi / 39 ft gainHike 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
Cowell-Purisima Coastal Trail
4.56.8 mi / 528 ft gainThis 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 -
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 -
Half Moon Bay, California
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 -
Half Moon Bay, California
Catch the Sunset at Maverick's Beach
5.01 miMaverick's beach is most well-known for the Maverick surf competition and the gnarly waves which surface here in the winter months. For the rest of the year, the beach is still a site to see. With huge waves crashing ¼ mile off shore and bluffs towering 100 feet above you, it’s a picturesque plac...Read more -
Half Moon Bay, California
Southern Beaches at San Gregorio State Beach
4.01.48 mi / 16 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 -
San Jose, California
Alviso Slough Loop
3.08.76 mi / 256 ft gainThis tranquil 20.6 acre park is open year round from 8am to sunset. It’s the gateway to the Don Edwards San Francisco Bay National Wildlife Refuge. It is filled with boardwalks, trails, and all kinds of wildlife. I went here with the sole intent of catching a pretty sunset after a long week. I g...Read more -
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