Trails Near Woodside, CA | Trailmonger

About trails near Woodside, California

61 named trails lie within about 25 miles of Woodside, covering 182 miles in total. 57 of them are tagged for hiking and 27 for mountain biking.

The closest is Bear Gulch Trail, about 0.0 miles away. 61 of them lie within 10 miles of town. The longest nearby is Bay Area Ridge Trail - 04 - San Francisco and Peninsula, at 60.9 miles. These trails fall in San Mateo County.

What the trails near Woodside are like

By length, 18 are under a mile, 38 run 1 to 5 miles, and 5 are 5 miles or longer.

Of the 33 with a difficulty rating, 19 easy, 10 moderate, and 4 hard. Of the 60 with measured elevation, Purisima Creek Trail climbs the most, about 5,570 ft, and 17 gain 1,000 ft or more.

All 61 trails, nearest first

Bear Gulch TrailHikeSan Mateo County5.1 mi Trail8HikeSan Mateo County0.3 mi Bay Tree TrailHikeSan Mateo County0.8 mi Clarkia TrailHikeSan Mateo County0.9 mi Redwood Nature TrailHikeSan Mateo County0.8 mi Meadow TrailHikeMTBSan Mateo County2.5 mi Chickadee Nature TrailHikeSan Mateo County0.4 mi Madrone TrailHikeSan Mateo County1.9 mi Oak TrailHikeSan Mateo County0.5 mi Redwood TrailHikeMTBSan Mateo County1.3 mi Crystal Springs TrailHikeSan Mateo County9.1 mi Alambique TrailHikeSan Mateo County4.7 mi Dean TrailHikeSan Mateo County2.1 mi Chapparal TrailHikeSan Mateo County0.4 mi Archery Fire Road;Skyline TrailSan Mateo County0.1 mi Chinquapin TrailHikeSan Mateo County1.6 mi Campground TrailSan Mateo County1.0 mi Skyline TrailHikeSan Mateo County13.7 mi Cielo TrailHikeSan Mateo County1.5 mi Sprout TrailHikeSan Mateo County0.2 mi Miramontes TrailHikeSan Mateo County1.2 mi Summit Springs TrailSan Mateo County0.6 mi Richards Road TrailHikeSan Mateo County4.0 mi Molder TrailHikeSan Mateo County0.4 mi Lone Madrone TrailHikeSan Mateo County1.2 mi Mount Redondo TrailHikeSan Mateo County0.8 mi Coho Vista TrailHikeSan Mateo County3.2 mi Steam Donkey TrailHikeMTBSan Mateo County1.0 mi Tafoni TrailHikeMTBSan Mateo County2.1 mi Fir TrailHikeMTBSan Mateo County1.7 mi Oljon TrailHikeMTBSan Mateo County1.6 mi Lonely TrailHikeSan Mateo County1.6 mi Raymundo TrailHikeSan Mateo County1.5 mi Gordon Mill TrailHikeMTBSan Mateo County2.5 mi Unofficial Skyline TrailHikeSan Mateo County1.0 mi El Corte de Madera Creek TrailHikeMTBSan Mateo County3.1 mi Crossover TrailHikeMTBSan Mateo County0.4 mi Manzanita TrailHikeMTBSan Mateo County1.2 mi Resolution TrailHikeMTBSan Mateo County1.0 mi Crosscut TrailHikeMTBSan Mateo County0.5 mi Spring Board TrailHikeMTBSan Mateo County1.7 mi Purisima Creek TrailHikeMTBSan Mateo County6.6 mi Methuselah TrailMTBSan Mateo County3.7 mi Timberview TrailHikeMTBSan Mateo County2.3 mi Blue Blossom TrailHikeMTBSan Mateo County1.3 mi North Leaf TrailHikeMTBSan Mateo County0.7 mi Lawrence Creek TrailHikeMTBSan Mateo County2.8 mi Giant Salamander TrailHikeMTBSan Mateo County1.1 mi Craig Britton TrailHikeSan Mateo County2.5 mi South Leaf TrailHikeMTBSan Mateo County1.4 mi Grabtown Gulch TrailHikeMTBSan Mateo County1.9 mi Bald Knob TrailHikeSan Mateo County1.2 mi Bay Area Ridge Trail - 04 - San Francisco and PeninsulaHikeSan Mateo County60.9 mi Borden Hatch Mill TrailHikeMTBSan Mateo County2.4 mi Chris Macintosh TrailHikeSan Mateo County0.5 mi Virginia Mill TrailHikeMTBSan Mateo County2.1 mi Irish Ridge TrailHikeSan Mateo County1.2 mi Whittemore Gulch TrailHikeMTBSan Mateo County2.6 mi North Ridge TrailHikeMTBSan Mateo County2.0 mi Harkins Ridge TrailHikeMTBSan Mateo County3.1 mi Lobitos Creek TrailHikeSan Mateo County0.6 mi

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San Mateo County

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Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 4, 2026.