Woodside
Trail Running Calendar near Woodside 2026-2027
Explore the top trail runs near Woodside for 2026-2027! We've gathered 61 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A 40th edition cross country meet in Golden Gate Park with an approximately 4 mile two loop course over grass, dirt, and rolling hills.
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.
Trail 5K at San Pedro Park with a hilly, technical first mile; a kids run and a members only picnic follow.
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 races at Sanborn County Park on Sep 27, 2026 through shaded redwood forest with steep climbs and flowy singletrack.
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.
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.
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.
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.