Trail Running calendar near Cupertino 2026-2027

The Rocky Ridge 2026 offers a challenging half marathon trail run in the Las Trampas Wilderness, plus 10K and 5K options. It's the finale for the Ultra Half Marathon Series and supports the East Bay Regional Parks Campership Program. Partic..

The Dick Collins Firetrails carries on a historic ultrarunning tradition at Lake Chabot. Runners can choose from three classic distances: a 100k, a 50 miler, and a marathon. It's a UTMB Index event with firm time limits due to park regulati..

Event Overview The 2026 Big Sur Trail Marathon, Half Marathon & 5 Mile is the 36th annual running of this event. It takes place at Andrew Molera State Park in Big Sur, California. Distances The event offers three distances: Marathon Ha..

Explore the shaded redwood groves and challenging, flowy singletrack of Sanborn County Park. This trail event on September 27, 2026, offers 10k, half marathon, and 50k distances through the Santa Cruz Mountains.

Run by the Sea returns for its tenth year at Wilder Ranch State Park. This coastal run on flat dirt trails offers a half marathon, a 12K, and a 4K run/walk. The event supports local youth and trail stewardship programs.

Run the 39th Ruth Anderson Memorial Endurance Run on October 10, 2026 in San Francisco. Choose 100 km, 50 miles, or 50 km on a scenic paved loop around Lake Merced with chip timing and certified 50K and 50 mile courses.

Event Overview The Diablo Summit Stomp is a trail race held on October 17, 2026, in Walnut Creek. The event offers several distances run on dirt trails. Distances and Courses Participants can choose from one of four courses: 30K Half Marat..

A Halloween-themed running event at Hellyer County Park offering distances from a kid's 50 yd dash to a certified marathon, with costume prizes, aid stations every 2-4 miles, and cupless hydration policy.

A trail fundraiser in Joaquin Miller Park offering a 5 km trail race and a 1 mile fun run/walk to support Oakland Tech PTSA and the school cross country program; donations are tax-deductible.

Mermaid Trail Run at Huddart Park in Woodside on November 7, 2026 features multiple trail distances, a timed 6 Hour challenge and a youth dash. The course is hilly, parking has a cash fee and a pancake breakfast follows the race.

This trail run takes place at Lake Chabot Regional Park in Castro Valley, featuring distances from 8K to 50K. The cupless event is known for its clearly marked loops around the popular reservoir. All finishers get a custom medal, with aid s..

This November trail run takes on the iconic slopes of Mt. Tamalpais, starting at Stinson Beach. Runners can choose from four distances, from a 10K to a 50K ultramarathon, all featuring significant climbs and views. The event includes chip t..

A Thanksgiving morning event in San Jose offering 5K, 10K, a USATF certified half marathon, age-group races and a free kids' 50-yard dash. The course is mostly asphalt, aid stations appear every 2 to 4 miles, and the event is cupless.

Event Details The Quarry Turkey 2026 is scheduled for Saturday, November 28, 2026. It is held at the Quarry Lakes Regional Recreation Area on Isherwood Way in Fremont, California. Distances The event offers several race distances: Half Mar..

Escape the wrath of Krampus with this themed cross-country run in San Francisco or from anywhere. Choose from 5K, 10K, or a nine-mile course. All finishers get unique Krampus themed swag, including a woodallion and beer stein.

This event takes runners on flat, fast courses through the scenic Quarry Lakes park and along the Alameda Creek Trail. It features multiple distances including a certified half marathon, plus special youth and free kids' races. All finisher..

The Calero Trail Run (Winter) takes place on the trails of Calero County Park in San Jose. Runners can choose from a wide range of distances, from a 1-mile run to a 50K ultramarathon. The courses feature hills, single-track, and panoramic v..

The Hunter S. Thompson Fear & Loathing will take place in San Francisco on Sunday 6 December 2026. You can run between 50 and 50 miles.

Run through the redwoods and pines of Sanborn County Park. Choose from a half marathon, 10K, or 5K on scenic single-track trails. Walkers are welcome and all finishers get a medal.

Ring in the new year with a trail run at Lake Chabot. Choose from a half marathon, 10K, or 5K on New Year's Eve. For a special challenge, run both days to earn the Mega-Medal.