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.
March 2027
Point to point half marathon from the Hacienda Entrance up to Mt Umunhum with 4,767 feet of ascent, marked aid stations, drop bag service and shuttle transport back to the start.
A running event at Quarry Lakes Regional Recreation Area in Fremont offering a Half Marathon, 10K and 5K on a mostly-flat course along the historic Western Pacific Trail.
April 2027
Trail race at Santa Teresa County Park on April 3, 2027 offering 5K, 10K, 10 mile and half marathon on marked, hilly trails.
Badger Cove is a running event in Livermore, CA on April 17, 2027 offering a half marathon, 10K, 5K and a hiker division. Registration opens January 1 and closes February 2 with fees varying by event.
A 5K mud and obstacle run at Club Moto in Livermore on April 17, 2027 with required signed waiver, a spectator fee, and listed entry prices.
A trail event at Lake Chabot Regional Park offering distances from a 50‑yard kids dash to a 50K ultramarathon. The looped course circles the Lake Chabot reservoir and surrounding hills with measured distances.
No Foolin' Foot Race in San Carlos on April 24, 2027 offers 15K, 10K, 5K and a 1K kids trail course across Big Canyon, Eaton and Pulgas Ridge, with proceeds supporting local open space trail maintenance.
May 2027
Trail races, a beer mile, a one mile beer stroll, and post-run beer tastings at Almaden Lake Park in San Jose on May 29, 2027.
June 2027
Lake Chabot Trail Challenge on June 6, 2027 in Castro Valley features a chip timed half marathon and a 5K on scenic trails and roads.
Trail ultras at Almaden-Quicksilver County Park on June 12, 2027, offering 100K, 50M, 50K, marathon and 30K with marked courses, aid stations, drop bags and pacer support.
July 2027
Trail races in Santa Cruz through ancient coastal redwoods, meadows and ridges, with distances from a kids 0.25 mile run up to 50K.
July 24, 2027 at Lake Chabot Marina features 5K, 10K, half marathon, virtual 13.1 and a Half Marathon Hiker, with registration dates and published fees per event.