Cupertino
Trail Running Calendar near Cupertino 2026-2027
Explore the top trail runs near Cupertino for 2026-2027! We've gathered 45 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A trail run by Bay Area Run Crew at Stevens Creek Reservoir featuring varied terrain, trail-ready gear recommendations, and a post-run social at Voyager Craft Coffee.
November 2026
Trail races at Huddart Park in Woodside on November 7, 2026, with distances from 3 miles to a half marathon, a looped 6 hour challenge, kids dash and virtual options.
Experience a scenic trail run around the Lake Chabot reservoir and hills. With distances from a 50 yard kids dash to a 50K ultramarathon there is an option for everyone at this Castro Valley event.
A hilly trail running event at Rancho Cañada del Oro on November 13, 2027, offering distances from 5K to 50K with aid stations and strict time limits.
Trail and wilderness navigation in Santa Cruz with 2 hour and 4 hour formats, teams of one to five, and up to 20 checkpoints.
A Thanksgiving Day vegan fundraiser at San Leandro Marina featuring a flat 5K, canicross with dogs, a 1 mile walk, and kids races supporting the Milo Foundation.
Quarry Turkey in Fremont offers a half marathon, 10K, 5K and a virtual race over Thanksgiving weekend, plus a Little Turkeys kids race and a food drive.
December 2026
Trail races at Sanborn Regional Park on December 12, 2026: 5K, 10K and half marathon through redwoods with chip timing and finisher medals.
Trail races at Lake Chabot in Castro Valley on December 31, 2026 offering half marathon, 10K and 5K; hikers and walkers welcome.
January 2027
Multi-distance trail races at Lake Chabot across New Year's Eve and New Year's Day, including 5K, 10K, a half marathon and a virtual option.
Trail races at Almaden Quicksilver Park on January 2, 2027 offering distances from a kids run to a 50K with marked dirt road courses and multiple aid stations.
A mixed-surface running event at Coyote Hills Regional Park offering a half marathon, 10K, and 5K with updated courses, GPX files, and stocked aid stations.
February 2027
Trail races from 5K to 50K through eucalyptus forests and lakeside trails at Lake Chabot Regional Park near Castro Valley, CA.