Trail Running calendar near Woodside 2026-2027

Experience the scenic trails of Lake Chabot Regional Park with a variety of distances including a 5k, 10k, and half marathon. Enjoy a lively atmosphere with a post-race brewfest and handcrafted finisher awards.

A July 3, 2026 event at Sycamore Grove Park in Livermore with a flat 5K on mixed paved and dirt trails plus a free untimed 400 meter kids run for ages 12 and under. Registration windows and fees differ by race.

A map-based mystery run from Ghirardelli Square through classic San Francisco neighborhoods, with team navigation, chip-tagged checkpoints, 5K and 10K options, age and gender divisions, and post-event snacks and socializing.

Multiple trail distances from 5K to 50K on very hilly single track and dirt roads at Rancho Cañada del Oro. The course features scenic foothill views, two aid stations, enforced cutoffs, and finishers receive a medal.

Experience a scenic trail run through ancient Coastal Redwoods and lush river canyons in Santa Cruz. Choose from multiple distances including a 50K and marathon with several river crossings.

Experience the rugged beauty of Mt. Tamalpais and Muir Woods in this coastal trail event starting from Stinson Beach. Choose between 10K, Half Marathon, or 30K routes featuring steep climbs and breathtaking Pacific views.

Test your limits at Point Pinole Regional Shoreline with three 6 or 12 hour endurance runs on a scenic coastal loop. Enjoy a party atmosphere with an all day picnic and options for individual or team participation.

Trail running at Calero County Park with multiple distances across single track and dirt paths, significant climbs, aid stations and free parking at the park.

Trail races of 8K, half marathon, 30K and 50K run from Rodeo Beach through the Marin Headlands with coastal singletrack and ocean views. The event is limited to 350 runners and the 50K has an 8.5 hour time limit.

A classic trail event in Castro Valley offering 50K and 21K loop courses through East Bay Regional Parks, with on-course aid stations, volunteer support, race swag, and age-group awards.

Test your endurance at Skyline Wilderness Park in this time based trail run where you complete as many laps as possible in three, six, or twelve hours. Enjoy rolling hills and scenic singletrack in the heart of Napa.

Experience a trail run through redwood trees and mountain peaks at the Mt. Madonna Challenge. Choose between steep 5K, 10K, and Half Marathon courses while supporting local youth running scholarships.

Bear Creek 2026 in Lafayette California offers a half marathon, 10K, 5K and a remote runner option on August 8, 2026. The trail course includes hills, scenic views and a final mile of downhill shaded single track.

A 50K single loop ultramarathon around the Marin Headlands with about 6,500 feet of elevation gain, varied trail and fire road terrain, and start and finish at Santos Meadows. A Kids One Mile Challenge is also offered.

Experience the trails of Redwood Regional Park in Oakland. Runners can choose from distances ranging from a 50 yard kids dash to a 50K ultramarathon through scenic ridge lines and redwood groves.

Trail races on hilly mixed dirt and single track at Almaden Quicksilver Park with distances from 5K to 50K, aid stations, drop bag service for longer races, and mandatory course markings and cutoffs.

Trail races of 10K, half marathon and 30K through Henry Cowell Redwoods State Park with single track, sand ridge and river crossings. Aid stations are spaced every five to six miles and the event is cupless.

Navigate through historic San Francisco neighborhoods and parks in this unique 5K or 10K challenge. Use a custom map to find checkpoints and solve riddles individually or in teams of up to five people.

The Double Dipsea is a longstanding annual 13.7 mile trail race from Stinson Beach to Mill Valley and back, run on mostly single track with many stairs and handicapped starts that create frequent passing among runners.

A scenic loop trail race around Angel Island with a single-loop 10K and a half marathon that runs the loop twice; ferry transport is required and included in race pricing, and the field is limited to 400 participants.