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.
August 2026
A two loop 4.15 mile cross country race on the fire roads of the UC Santa Cruz campus, starting and finishing at the meadow above the fire station and included in the Pacific Association USATF Grand Prix series.
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.
Trail event in Castro Valley featuring a 100k, 50 mile, and marathon with UTMB index status and firm time limits due to park permits.
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
Run by the Sea at Wilder Ranch State Park on October 4, 2026 offers a Half Marathon, 12K and 4K run/walk along mostly flat packed dirt trails with coastal bluff and Monterey Bay views. Organized by the Santa Cruz Track Club; proceeds benefit local gr..
A multi-distance in-person and virtual run along the Coastal Trail in Half Moon Bay that raises funds for Senior Coastsiders' programs for older adults.
November 2026
Trail trail event at Huddart Park in Woodside offering distances from a 1 mile kids dash to a Sirena 6 hour individual and relay challenge.
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.