Trail Running calendar near Cupertino 2025-2026

The Calero Hills Trail Fest is an exciting trail running event held at Calero County Park in San Jose, CA. Participants can choose from various distances, including a marathon, 30K, half marathon, 10 miler, 10K, and 5K. The course features challenging ascents and descents through scenic oak groves,..

The Skyline 50K Endurance Run is one of the oldest continuously running 50K races in the United States, taking place annually in August at Lake Chabot Marina in Castro Valley, California. This event is designed for both first-time ultrarunners and seasoned veterans, featuring a scenic course that lo..

Bear Creek Run is a trail running event taking place in Lafayette, California, featuring a Half Marathon, 10K, and 5K on August 9, 2025. The courses are known for their challenging hills, offering participants a scenic experience through Briones Regional Park. Hikers and walkers are welcome, making..

The Mount Madonna Challenge is an annual trail running event held in Gilroy, California, featuring 5K, 10K, and half marathon distances. Participants run through scenic trails among towering redwood trees, with routes offering stunning views of Santa Clara, Santa Cruz, and San Benito County. Establi..

The Almaden Hills Trail Run is an exciting running event held at Almaden Quicksilver Park in San Jose, California. Participants can choose from various distances, including 5K, 10K, 8M, Half Marathon, 30K, Trail Marathon, and 50K, catering to runners of all skill levels. The course features a mix of..

The Tamalpa Headlands 50K is a challenging ultramarathon set in the stunning Marin Headlands, California, featuring a single-loop course that showcases iconic trails such as Coastal, Miwok, and Dipsea. Established in 1998, this event is presented by Nike Trail and the Tamalpa Runners, and it include..

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 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 SPASM Crystal Springs Trail Run is an exciting running event taking place in Woodside, California, featuring a variety of race distances including an 8K, Half Marathon, 35K, Marathon, and 50K, along with a free Kid's Run for children aged 6 and under. Set against the stunning backdrop of Huddart..

The Stevens Creek Striders Reservoir Run offers a scenic and challenging experience for runners of all levels, featuring a Half Marathon, 11K, and a Lollipop Loop (2.5 miles). Set in Cupertino, CA, participants will traverse beautiful trails, including shaded single tracks and open vistas. The event..

The Diablo Trail Run, scheduled for September 7, 2025, in Clayton, California, offers a variety of race distances including 4 miles, 10 miles, a half marathon, a marathon, and a 50K, along with a free Kid's Run for children aged 6 and under. The event takes place in the scenic Mount Diablo State Par..

The Rocky Ridge Trail Half Marathon is set to take place on September 20, 2025, in the scenic Las Trampas Wilderness of San Ramon, California. This challenging event is part of the Brazen Ultra Half Series and features a half marathon, along with 10K and 5K options. Participants can expect a rugged..

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 an exciting running event taking place at San Pedro Valley State Park in Pacifica, CA. Participants can choose between a 10K and a Half Marathon, both offering stunning views of the Pacific Ocean coastline and challenging switchbacks. This event is designed for runners of..

The Star City San Bruno Mountain Half Marathon, organized by the Excelsior Running Club, will take place on October 4, 2025. This scenic race features a challenging 13.1-mile course that is 93% on trails, with an elevation gain of 2,400 feet, offering stunning views of the Pacific Ocean, Bay, and Sa..

The Women's Headlands Half Marathon, taking place on October 4, 2025, in the scenic Marin Headlands, offers a challenging and beautiful course for runners. Participants can choose between a half marathon (12.6 miles) and a 10K (6 miles), both starting and finishing at Rodeo Beach. The event showcase..

The Ruth Anderson Memorial Endurance Run is a prestigious running event held annually in San Francisco, California, since 1986. This endurance race features multiple distances, including 50 miles, 100 kilometers, and 50 kilometers, attracting runners of various skill levels. The course consists of a..

The Haunted Hills 10K in Redwood City is a unique running event scheduled for October 25, 2025. Participants can form teams of 1 to 5 and embark on a fun-filled adventure through the festively decorated neighborhoods. Runners will navigate approximately 36 checkpoints on the 10K course, answering si..

The ZombieRunner Halloween event is a festive running competition taking place in San Jose, CA, featuring a variety of race distances including a 5K, 10K, Half Marathon, and Marathon, along with special categories for younger participants. Runners are encouraged to don Halloween costumes for a chanc..

The Oakland Tech 5km Fundraiser Race and 1 Mile Fun Run/Walk is an exciting event taking place at Joaquin Miller Park, aimed at supporting the Oakland Tech Cross Country and Track Team. Participants can choose between a challenging 5K trail run or a more leisurely 1-mile fun run/walk, both set again..