Woodside
Trail Running Calendar near Woodside 2026-2027
Explore the top trail runs near Woodside for 2026-2027! We've gathered 58 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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.
Off road 5K on San Bruno Mountain with about 300 ft elevation gain, starting and finishing at the picnic area and routing via Old Guadalupe Trail and Saddle Loop Trail.
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.
Trail races at Almaden Quicksilver County Park offering a half marathon, 10K and kids 1 mile with historic mining views and local conservation support.
Scenic coastal 5K, 10K, half marathon and kids run in Half Moon Bay that raises funds for Senior Coastsiders; every participant receives a pumpkin.
Virtual worldwide challenge and an in-person gathering at the San Francisco Ferry Building on October 24, 2026, fundraising for the Breast Cancer Research Foundation.
November 2026
A fundraiser in Joaquin Miller Park featuring a 5 km trail race and a 1 mile fun run to support Oakland Tech PTSA and student programs.
Trail races at Huddart Park with multiple distances, cupless aid stations, chip timing, post-race pancake breakfast, and awards for female finishers.
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.
Thanksgiving Day 5K and canicross fundraiser at San Leandro Marina with races for adults and kids, vegan refreshments, and animal welfare fundraising.
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
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.