Trail Running calendar near Downtown San Jose 2025-2026

The Rodeo Valley Trail Run, held in the scenic Marin Headlands near Sausalito, CA, offers trail races of 8K, Half Marathon, 30K, and 50K distances. Starting near historic Fort Cronkhite and Rodeo Beach, the course features challenging steep climbs and descents along coastal trails with stunning view..

The Skyline 50K Endurance Run, held annually in August at Lake Chabot Marina in Castro Valley, California, is one of the oldest continuously running 50K races in the U.S. The course features a large loop through the scenic East Bay Regional Parks, reaching Skyline Gate. Known for its welcoming atmos..

The Mount Madonna Challenge, held in Gilroy, California, is a historic trail running event featuring a half marathon, 10K, and 5K races. Known for its challenging elevation gains—2,828 feet for the half marathon, 1,532 feet for the 10K, and 843 feet for the 5K—the course offers a rigorous test of en..

Bear Creek is a trail running event held in Lafayette, California, featuring a half marathon, 10K, and 5K distances. The races take place on challenging courses with many hills through the scenic Briones Regional Park, offering a rewarding experience for trail runners rather than a flat, fast course..

The Redwood (Summer) Trail Run is an exciting running event taking place in Oakland, California, featuring a variety of race distances including a 5-mile run, Half Marathon, 30K, Marathon, and 50K, along with a free Kid's Run for children aged 6 and under. The course winds through the scenic Redwood..

The Tamalpa Headlands 50K is a challenging ultramarathon held annually in Marin County, California, starting and finishing at Santos Meadow near Muir Woods. Covering a 50-kilometer single-loop course, the race features approximately 6,500 feet of elevation gain across iconic trails such as Coastal,..

The Almaden Hills Trail Run - Summer is a challenging trail running event held at Almaden Quicksilver Park in the scenic Almaden Valley, San Jose, California. The course features a mix of 60% dirt roads and 40% single-track trails with significant hills, offering runners beautiful countryside views...

The Envirosports Angel Island Half Marathon & 10K is an annual race held at Angel Island State Park near Tiburon, California. The event features a scenic, hilly loop trail that circumnavigates Angel Island, offering stunning panoramic views of the Golden Gate Bridge, San Francisco, Alcatraz Island,..

The Double Dipsea is a challenging 13.7-mile trail run that takes place annually, starting at Stinson Beach, California. First held in 1970, this race is known for its unique handicapped start format, where slower runners begin first, creating a dynamic environment of constant passing on narrow trai..

The Santa Cruz Trail Run, hosted by Inside Trail Racing, takes place at Henry Cowell Redwoods State Park in Felton, California. This scenic event features three distances: 10K, Half Marathon (13.5 miles), and 30K (18.2 miles), with challenging elevation gains up to 3,250 feet. The course winds throu..

Run-de-Vous is a community-focused running event held at Harvey Bear Ranch Park in San Martin, California, on August 29, 2025. The race features multiple distances, including 100 miles, 100K, 50 miles, marathon, 50K, and a 4-person 50M relay. The course is a fast, manageable 2-mile loop set against..

The SPASM Crystal Springs Trail Run is an exciting running event taking place in Huddart Park, Woodside, CA. Scheduled for August 31, 2025, it features multiple race distances including an 8K, Half Marathon, 35K, Marathon, and 50K, along with a free Kid's Run for children aged 6 and under. Participa..

The Stevens Creek Striders Reservoir Run, held in Cupertino, CA, offers a scenic trail running experience with distances of a Half Marathon (13.2 miles), 11K, and a 2.5-mile Lollipop Loop charity run/walk. The course features shaded single-track trails and open vistas, including challenging steep as..

The Diablo Trail Run, held at Diablo State Park in Clayton, California, offers a variety of scenic trail running events on September 7, 2025. Participants can choose from distances including 4 miles, 10 miles, half marathon, marathon, and 50K, with a free Kid's Run also available. The course feature..

The South Hills Single Track Trail Run - Summer, held at Calero County Park in San Jose, CA, offers a variety of distances including 50K, trail marathon, 16-mile, half marathon, 9-mile, 10K, 5K, mile, and a kids run. The course features challenging single track trails, hills, dirt paths, oak trees,..

The Berkeley Trail Adventure is a scenic trail running event held in Berkeley, California, within Tilden Regional Park and Wildcat Canyon. It offers four race distances: 10K, half marathon, 35K, and 50K, featuring technical dirt trails, fire roads, and some asphalt sections. The course showcases sha..

The Mt. Umunhum Marathon, Race to the Top and Down, is a challenging trail marathon held in Almaden Quicksilver County Park, San Jose, California. The race begins at the Hacienda Entrance and ascends to the summit of Mt.Umunhum, offering runners a demanding climb followed by a thrilling descent back..

The Rocky Ridge Trail Half Marathon is a challenging trail race held in the scenic Las Trampas Wilderness near San Ramon, California. Scheduled for September 20, 2025, the event features a half marathon, 10K, and 5K distances. Known for its tough terrain and significant elevation changes, the half m..

The Dick Collins Firetrails will take place in Castro Valley from Saturday 27 September 2025 to Sunday 28 September 2025. You can run between 42 and 100 kilometers.

The Pacifica Summit Run is a scenic trail running event held at San Pedro Valley State Park in Pacifica, California. It offers two race distances: a 10K and a half marathon. Runners experience challenging switchbacks and enjoy stunning postcard views of the Pacific Ocean coastline from the tallest m..