Cupertino
Trail Running Calendar near Cupertino 2026-2027
Explore the top trail runs near Cupertino for 2026-2027! We've gathered 47 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
A trail running event at Calero County Park offering distances from a kids run to a 50K across single-track and dirt roads, with named aid stations, drop bag support, bib color assignments, and time limits for longer races.
Community walk and hike on September 12, 2026 at Harvey Bear Ranch with bus transport, vegetarian meals, and free registration from July 22 to September 13.
Historic Bay Area trail event offering 100K, 50 mile and marathon courses, all UTMB indexed with the 50 mile in the Pacific USATF Grand Prix.
Trail running in shaded redwood forest at Sanborn County Park on September 27 2026, with 10K, half marathon and 50K options; steep singletrack, shuttle parking, chip timing and specific mandatory gear for the 50K.
October 2026
21st Annual Garin Park XC Challenge at Garin Regional Park is a USATF Pacific Association cross country meet with about 5K courses featuring hills, scenic views, and a half mile flat finish.
Run by the Sea at Wilder Ranch State Park on October 4, 2026 features a half marathon, 12K and 4K on mostly flat coastal bluff trails.
A trail race at Almaden Quicksilver County Park with distances from 5K to 50K. Courses are out-and-back, marked with colored ribbons, include aid stations and toilets, and the longer races reach Bald Mountain and Mt. Umunhum.
Annual Pumpkin Run in Half Moon Bay on October 18, 2026 with 5K, 10K, half marathon and a kids fun run along the Pacific Coastal Trail benefiting Senior Coastsiders.
November 2026
Trail event at Huddart Park offering multiple distances, a 6 Hour Challenge, cupless aid stations, post-race pancake breakfast and female-only awards.
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 fall trail event at Rancho Cañada del Oro Open Space Preserve offering distances from 5K to 50K on hilly single-track and dirt roads, with aid stations, multiple water stops, strict cutoff limits, and limited parking.
Explore the redwood forests and meadows of Santa Cruz in this 2 or 4 hour map adventure. Navigate through wilderness trails in teams of up to five to find hidden checkpoints and test your navigation skills.