Cupertino
Trail Running Calendar near Cupertino 2026-2027
Explore the top trail runs near Cupertino for 2026-2027! We've gathered 46 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A map-based 2- or 4-hour team scramble through Santa Cruz redwoods and meadows with timed checkpoints and on-site timing chips.
A Thanksgiving Day 5K and 1 mile event at San Leandro Marina with canicross teams, kids races, and proceeds benefiting animal welfare; the course is flat with mixed surfaces and free parking is available.
A Thanksgiving weekend race at Quarry Lakes offering a half marathon, 10K, 5K and a free short Little Turkeys run, plus a food drive and a two-day medal challenge.
December 2026
Trail running at Calero County Park near San Jose on Dec 5, 2026, offering distances from a kids run to a 50K with marked courses and aid stations.
Trail races through redwood groves in Sanborn Regional Park on December 12, 2026 with 5K, 10K and half marathon options, chip timing and finisher medals.
Trail races on the Lake Chabot trails in Castro Valley on December 31, 2026 offering half marathon, 10K and 5K; hikers and walkers welcome.
January 2027
Lake Chabot trails in Castro Valley host Brazen New Year's Day on January 1, 2027 with half marathon, 10K, 5K plus remote and hiker options.
A trail race in Huddart Park near Woodside CA on January 17, 2027 offering distances from an 8K to a 50K plus a free kids 50 yard dash. Courses run through redwoods, are well marked, and feature stocked aid stations.
Mixed-surface races at Coyote Hills Regional Park in Fremont offering half marathon, 10K and 5K with aid stations, GPX files and a half-marathon hiker division.
February 2027
Trail races at Lake Chabot Regional Park near Castro Valley with 50K, 30K, half marathon, 10K and 5K options, organized by Inside Trail Racing.
March 2027
A multi-distance trail event on March 22, 2025 at Calero County Park in San Jose offering runs from a kids race to a 50K, single track and dirt-road courses, multiple aid stations, and per-distance time limits.
A spring race at Quarry Lakes Regional Recreation Area in Fremont on March 27, 2027 offering half marathon, 10K, 5K and a remote runner option.
April 2027
A spring trail race at Pueblo Day Use Area in Santa Teresa County Park on April 5, 2025 offering 5K, 10K, 10 Mile and a half marathon across marked, hilly trails with aid stations and a four hour half marathon limit.