Woodside
Trail Running Calendar near Woodside 2026-2027
Explore the top trail runs near Woodside for 2026-2027! We've gathered 62 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
An October fundraiser offering a global virtual challenge plus an in-person event at San Francisco’s Ferry Building. Multiple distances from 5K to 50K are available; some courses are unmarked and maps are provided. Proceeds support the Breast Cancer..
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.
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
A seasonal cross country event in San Francisco on 12/6/2026 with live and virtual options. Distances include a 5K, 10K, and a nine mile course; all entrants receive race swag and there is a pre race bib and shirt pickup with Brewfest.
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.
Single-loop urban ultramarathon in San Francisco from Twin Peaks offering 50 mile and 50K options, informal aid stations, and a mile 25 cutoff.
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.