Trail Running calendar near Cupertino 2025-2026

We have found 88 Trailruns within 80 miles of Cupertino. See below where and when you can find the races.

The Golden Gate Headlands Marathon, Half Marathon, and 10K is a scenic running event taking place in the Marin Headlands, California, on April 5, 2025. Celebrating its 40th annual edition, the race offers participants breathtaking views of the San Francisco Bay, the Pacific Ocean, and the iconic Gol..

The Diablo Trails Challenge is a running event taking place on Mount Diablo, featuring multiple race distances including a 50K, half marathon, 10K, and 5K. Scheduled for April 5, 2025, this challenge caters to runners of all experience levels, from beginners to seasoned ultra-runners. A portion of t..

The 2025 Romancing the Island Half Marathon & 10K is set to take place at Angel Island State Park in Belvedere Tiburon, California. This annual event, now in its 34th year, features a scenic loop trail that offers breathtaking views of the Golden Gate Bridge, San Francisco, and surrounding areas. Pa..

The SPASM Lake Chabot Trail Run is a diverse running event taking place at Lake Chabot Regional Park in Castro Valley, California. Scheduled for April 12, 2025, it features multiple race distances including an 8K, Half Marathon, 30K, Marathon, and 50K, along with a free Kid's Run for children aged 6..

The Rodeo Beach Rumble is an exciting running event taking place in the stunning Golden Gate National Recreation Area, near San Francisco. Participants can choose between an 8K and a Half Marathon, both offering breathtaking views of the Bay Area and historical military landmarks along the routes. T..

The Woodside Crossover is a trail running event taking place on April 12, 2025, at Huddart County Park in Woodside, California. This scenic race features four distances: 10K, Half Marathon, 35K, and 50K, catering to runners of all skill levels. Participants will navigate through beautiful trails sur..

The Sierra Azul Trail Challenge is an exciting running event taking place in the scenic Sierra Azul Open Space Preserve, near San Jose, CA. Participants can choose from various distances, including a 50K, Trail Marathon, 20 Mile, Half Marathon, 7 Mile, and 5K. This challenging race offers a unique o..

The Badger Cove Half Marathon, along with 10K and 5K events, will take place on April 19, 2025, in Livermore, California, at Lake Del Valle Regional Park. This trail race invites participants of all levels, including walkers and hikers, to enjoy the scenic emerald hills. Runners will receive custom..

The Horseshoe Lake Trail Run is a scenic running event taking place at the Skyline Ridge Open Space Preserve in La Honda, California. Scheduled for April 20, 2025, the event features multiple race distances, including a 5-mile run, half marathon, 30K, marathon, and 50K, along with a free Kid's Run f..

The No Foolin' Foot Race is an annual running event organized by the Parks and Recreation Foundation of San Carlos, featuring a challenging 5k and 10k course through the scenic Big Canyon and Eaton Parks. Participants can also enjoy a 1-mile course designed for children aged 5-10. The event includes..

The Mt. Tam Wild Boar Half Marathon and 10K is an annual running event held at Mt. Tamalpais State Park in Mill Valley, California.Celebrating its 37th year in 2025, the race features a scenic coastal ridge trail that offers stunning views of the Pacific Ocean and surrounding landscapes. Participant..

May 2025

The Hacienda Hills Trail Run - Spring is an exciting trail running event taking place at Almaden Quicksilver County Park in San Jose, California. Scheduled for May 3, 2025, this event features nine different race distances, including a 50K, Trail Marathon, 30K, Half Marathon, 9 Mile, 10K, 5K, Mile,..

The Miwok 100K is a renowned trail ultramarathon celebrated for its stunning scenery and challenging course, featuring 11,800 feet of elevation gain. Set in the picturesque Stinson Beach area, participants enjoy breathtaking views of San Francisco, the Golden Gate Bridge, and the surrounding natural..

The Muir Woods Marathon, held annually, offers a challenging trail running experience through the scenic landscapes of Muir Woods and Stinson Beach, California. Participants can choose from three distances: a full marathon, a half marathon, and a 7-mile run. The course features steep climbs, wooden..

The Grizzly Peak Trail Run, scheduled for May 10, 2025, in Berkeley, CA, offers a variety of race distances including a 10K, Half Marathon, 30K, Marathon, and 50K, along with a free Kid's Run for children aged 6 and under. The event starts at Lake Anza and traverses the scenic trails of Tilden Regio..

The Nitro Trail 2025 is an exciting running event taking place at Point Pinole Regional Shoreline Park in San Pablo, California. Participants can choose from three race distances: a half marathon, 10K, and 5K, making it suitable for runners of all levels. The event celebrates the park's transformati..

The Quicksilver Endurance Runs, taking place in San Jose, CA, features both 50K and 100K races on scenic, challenging trails. Celebrating its 40th edition, the event offers runners a chance to experience beautiful oak forests, meadows, and stunning views of the Santa Clara Valley and Santa Cruz Moun..

The Race for Open Space is a multi-course trail running event designed to raise funds and awareness for the Big Sur Land Trust, taking place in the scenic Palo Corona Regional Park. Participants can choose from various distances, including a 1-mile fun run, a 5k, and longer options up to 35k+. This..

The 13 Mile Trail Race Top Down is a half marathon event taking place in San Jose, California, on May 17, 2025. The race features a scenic course that traverses two beautiful parks: Almaden Quicksilver Park and Sierra Azul Open Space Preserve. Participants will be transported to the starting point a..

The Pacifica Foothills Trail Run, hosted by Inside Trail Racing, offers a scenic running experience in San Pedro Valley County Park, Pacifica, CA. Participants can choose from three distances: 10K, Half Marathon, and 30K, all set against the backdrop of the Santa Cruz Mountains. The event features m..