Woodside
Trail Running Calendar near Woodside 2026-2027
Explore the top trail runs near Woodside for 2026-2027! We've gathered 63 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A waterfront 5K through Crissy Field and Fort Point Promenade in San Francisco on August 30, 2026, with live and virtual entry options and advance registration required.
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.
A 40th edition cross country meet in Golden Gate Park with an approximately 4 mile two loop course over grass, dirt, and rolling hills.
Rocky Ridge in the Las Trampas Wilderness near San Ramon on September 19, 2026 features a half marathon, 10K and 5K on hilly trail terrain with remote runner options.
Family friendly Jog in the Fog 5K in San Francisco with a scenic 3.4 mile course, post race activities, age group awards, and a race t shirt for registrants.
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
Experience a trail half marathon on San Bruno Mountain featuring 2,400 feet of elevation gain and stunning views. Enjoy a scenic route with 93 percent trail coverage followed by a post race meal and finishers medal.
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.
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.
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.