Trail Running calendar near Cupertino 2026-2027

Timed loop endurance races at Point Pinole on July 25, 2026 offering 12, 6 and 3 hour options for individuals or teams, with an all-day BBQ.

A trail race in the Marin Headlands with 8K, half, 30K and 50K options along coastal single-track and fire roads, marked courses, cupless aid stations, and a 350 runner capacity.

Monthly community hikes with an optional trail-run pace in Richmond, organized by FIERCE Advocates with Moving Forward and Richmond Run Club. Route details and gear recommendations are shared with registrants ahead of each meetup.

A historic 50k loop from and back to Lake Chabot Marina in Castro Valley with strong aid station support, a half marathon option, plant-based post-race food, and race swag including a shirt, socks, and medal.

A time based trail running event at Skyline Wilderness Park Napa on August 8 2026 offering 12 hour, 6 hour and 3 hour options plus relays. Main loop is about 4.1 miles with roughly 815 feet of elevation per lap and a short final loop.

A trail running event on Aug. 8, 2026 in Gilroy, California through redwood groves and peak viewpoints. Distances include a 5K, 10K and half marathon with significant elevation gain, and proceeds support youth scholarships.

Bear Creek on August 8, 2026 offers 5K, 10K and a 13.32-mile half marathon in the Briones Regional Park area, with a virtual Remote Runner option. Entry windows and fees are listed for each race.

A 50K trail ultramarathon near San Francisco with about 6,600 feet of climbing across Coastal, Miwok, Matt Davis and Dipsea trails and a $10,000 prize purse.

Experience the trails of Redwood Regional Park in Oakland. Runners can choose from distances ranging from a 50 yard kids dash to a 50K ultramarathon through scenic ridge lines and redwood groves.

Trail races on hilly mixed dirt and single track at Almaden Quicksilver Park with distances from 5K to 50K, aid stations, drop bag service for longer races, and mandatory course markings and cutoffs.

A five kilometer trail run along the Lands End Trail in San Francisco with views of the Golden Gate and the Pacific Ocean. The event lists a $10 entry fee, awards finisher ribbons, and requests no headphones or pets on course.

Oakland Cubs Back2School 5K and Fun Run on August 16, 2026 takes place at The Meadow in Oakland and raises funds for the youth running team and its scholarship programs. Distances include a 5K and a fun run.

A community running event in Felton, California, featuring a 10K through Henry Cowell Redwoods State Park and a 1 mile kids race, beginning and ending at Roaring Camp Railroads; registration includes a pancake breakfast and supports local e..

Trail races of 10K, half marathon and 30K in Henry Cowell Redwoods State Park featuring redwood single-track, a sandy ridge, river crossings, and cupless aid stations.

A map-based 5K and 10K in San Francisco where teams navigate checkpoints and answer multiple-choice questions, followed by refreshments at the finish.

A 13.7 mile trail race from Stinson Beach to Mill Valley and back on the Dipsea Trail. The annual handicapped event uses adjusted start waves and time cutoffs; 2026 marks the 56th running.

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.

Trail races at Huddart Park, King's Mountain and Bear Gulch offer measured distances from a 50 yard kids dash to a 50K, with fees listed per distance and registration opening November 11, 2025.

A scenic loop race on Angel Island offering a 10K and a two-loop half marathon with limited entry and required ferry access from Tiburon.

A steep 4.75 mile up and down run, hike, or walk on San Anselmo's Bald Hill that finishes downtown with live music and a t shirt. The third annual event benefits local nonprofits and includes town endorsement.