Trail Running calendar near Cupertino 2025-2026

The Big Sur Trail Marathon will take place in Monterey County on Saturday 27 September 2025. You can run between 5 and 26 miles.

The Pacifica Summit Run is a trail running event held at San Pedro Valley State Park in Pacifica, California. It features two race distances: a 10K and a half marathon. Runners experience scenic views from the tallest mountain on the upper San Francisco Peninsula, including stunning postcard vistas..

The Spartan Trail - San Jose Trail Challenge takes place in Sanborn County Park, located on the eastern slopes of the Santa Cruz Mountains near Saratoga, California. This scenic event offers three race distances: 10K, half marathon (21K), and 50K, featuring challenging, well-groomed trails with big..

The Trailblazer Race Mountain View will take place in Mountain View on Sunday 28 September 2025. You can run between 5 and 10 kilometers.

The Women's Headlands Half Marathon is a scenic 13.2-mile trail race held annually in the Marin Headlands near Mill Valley, California. Celebrating its third year in 2025, the event features a challenging course with nearly 2,000 feet of elevation gain, showcasing stunning singletrack trails, sweepi..

The Reservoir Dogs Trail Run in Orinda, CA, offers 10K, Half Marathon, and 35K distances around the scenic Briones Reservoir on East Bay Municipal Utility District (EBMUD) trails. This event features a mix of rolling fire roads, tree-covered single-track, and expansive views of watershed lands, prov..

The Star City San Bruno Mountain Half Marathon & 5K, held in Brisbane, California, offers a scenic trail running experience with spectacular views of the Pacific Ocean, San Francisco Bay, and the city skyline. The half marathon course is 93% trail, featuring 2,400 feet of elevation gain and a thrill..

The Women's Headlands Half Marathon is a trail running event held in the scenic Marin Headlands near Mill Valley, California. This race features a brand-new half marathon course that highlights the area's stunning singletrack trails, challenging climbs, and exhilarating descents, offering runners a..

Run by the Sea is an annual running event held at Wilder Ranch State Park in Santa Cruz, California. Scheduled for October 5, 2025, the race offers three distances: a 4K run/walk, a 12K run, and a half marathon. The courses primarily follow flat, packed dirt trails along the scenic coastal bluffs of..

The Mt. Umunhum Trail Conquest-Fall is a trail running event held at Almaden Quicksilver County Park in San Jose, California. The race offers multiple distances including a 5K, 7 Mile, Half Marathon, 30K, Trail Marathon, and 50K.The longer courses venture into the scenic Sierra Azul Open Space Prese..

Go Wild Marin 4 Hr is a trail and wilderness scramble event held on the Tiburon Peninsula in Corte Madera, California. Participants compete individually or in teams of up to five, using a custom map to locate as many as 24 checkpoints scattered across trails and wild areas within a four-hour time li..

The Ruth Anderson Memorial Endurance Run is an ultradistance race held annually in San Francisco, California, at scenic Lake Merced. The course features a mostly flat, USATF-certified 4.48-mile loop around the lake, combining asphalt paths and groomed dirt shoulders with about 100 feet of elevation..

The Napa Lapa Trail Adventure, held at Skyline Wilderness Park in Napa, California, is a unique time-based trail running event where participants run as far as possible within set time limits of 3, 6, or 12 hours. The course features a challenging 4.16-mile loop with approximately 815 feet of elevat..

The The John Lawson Tamalpa Challenge will take place in Santa Venetia on Sunday 12 October 2025. You can run between 4 and 4 miles.

The Diablo Summit Stomp is a trail running event held in Walnut Creek, California, featuring distances of 30K, half marathon, 10K, and 5K. The courses traverse dirt trails starting from Castle Rock Park and extend into Mount Diablo State Park, with the 30K route reaching the summit of Mount Diablo...

The Haunted Hills 10K in Redwood City is a unique nighttime running event featuring a spooky, fun atmosphere perfect for adults and families. Participants run in teams of 1 to 5, equipped with headlamps or flashlights, as they navigate through wickedly decorated neighborhoods. The course includes 36..

The Oakland Hills Trail Run, held at Redwood Regional Park in Oakland, California, offers three challenging distances: 10K, half marathon, and 35K. Set in a serene redwood forest with towering 150-foot coast redwoods, the course features technical dirt trails and fire roads with significant elevatio..

The Quicksilver Trail Challenge, hosted by the Quicksilver Running Club in San Jose, California, is an annual trail running event held in late summer or early fall at Almaden Quicksilver County Park. It features a half marathon, a 10K race, and a free one-mile kids' fun run. The courses traverse sce..

The Almaden Hills Trail Run - Fall takes place in Almaden Quicksilver Park, located in the scenic Almaden Valley near San Jose, CA. The event offers a variety of distances including 50K, trail marathon, 30K, half marathon, 10K, 8-mile, and 5K races. The course features a challenging mix of terrain,..

The ZombieRunner Halloween race takes place at Hellyer County Park in San Jose, California. Scheduled for November 1, 2025, it offers multiple distances including 5K, 10K, Half Marathon, Marathon, and age-specific 5K and 10K events, plus a free Kid's Run for children six and under. The courses are m..