Trail Running calendar near Cupertino 2025-2026

Enjoy scenic redwood trails at Huddart Park with distances from 3 Mile to Half Marathon, plus a family Mermaid Dash for kids. Try the festive 6 Hour Challenge to see how many 3 Mile loops you can cover, or join virtually.

Run scenic loops around Lake Chabot with distances from an 8K to a 50K, plus a free kids 50 yard dash. Expect rolling hills, marked trails, stocked aid stations and a friendly festival vibe for all abilities.

Run scenic, technical trails on Mt Tam with sweeping coastal views and big climbs, then celebrate with food and drinks on Stinson Beach. Four distances from 10K to 50K welcome every level of trail runner.

Take on the rolling, scenic trails of Rancho Cañada del Oro in Morgan Hill with distances from 5K to 50K. Expect challenging hills, mixed singletrack and fire road, creek crossings and big views framed by old oaks for a true trail running a..

Hit the trails along the Stanislaus River at the Ripon Turkey Trail Run, offering 5K, 10K and half marathon options for all levels. Enjoy a custom tech shirt, finisher medal and post race refreshments in a scenic park setting.

Test your endurance at The Captain’s Runaround in Riverbank on November 22, 2025, a timed loop race where you log as many miles as possible. Pick 8, 6, 4 or the new 2 hour sessions on a just under one mile loop at Jacob Myers Community Park..

The Golden Gate Trail Classic will take place in San Francisco from Saturday 22 November 2025 to Sunday 23 November 2025. You can run between 15 and 50 miles.

Celebrate Thanksgiving at the Zoom Turkey Trot in San Jose at Hellyer Park with a USATF certified half, 10K, 5K and kids runs, plus t shirts and finisher medals. Flat, fast courses and stocked aid stations welcome all abilities.

Celebrate Thanksgiving at the Moraga Turkey Trot, a friendly 5K or 1.5 mile run or walk on the Moraga Country Club cart path. Advance registration is required, proceeds benefit the food bank and participants get a tee, bib and prize chances..

Join the Quarry Turkey at Quarry Lakes on November 29 for a fast, mostly flat trail 5K, 10K or half marathon with a free kids sprint and family friendly Thanksgiving costumes encouraged. Proceeds benefit Alameda County Community Food Bank.

Quad Dipsea in Mill Valley is a brutal but beautiful 28.4 mile trail challenge with about 9,000 feet of climbing on the legendary Dipsea Trail. Stairs, steep single track and ocean views make the out and back to Stinson Beach an unforgettab..

Run Krampus Cross Country in San Francisco live on Dec 7 or virtually Dec 5 to 8 with 5K 10K and the Naughty Nine Miler. All entrants get a wooden woodallion a Krampus tee and a beer sampler stein plus a brewfest on Dec 5.

Tackle scenic singletrack and dirt at Calero County Park in the Calero Trail Run Winter, with distances from a kids mile to a 50K. Expect rolling hills, oak vistas, aid stations, a finishers medal and race day registration.

Run the scenic Alameda Creek Trail in Fremont at ZombieRunner Quarry Lakes with options from a kids dash to a full marathon. Flat trails, frequent aid stations, and a festive finish at Ensenada Pavilion.

Run scenic Marin trails at China Camp State Park with 30K (19.5 miles), Half Marathon (13.1 miles) or 10K. Expect technical dirt trails, a small field vibe, and a cupless format so bring your own bottle.

Run the iconic Hunter S. Thompson Fear & Loathing in San Francisco on December 7, a free grassroots single loop that winds past city landmarks and finishes at Twin Peaks. Choose 50 mile or 50K distances and help support Shoes For Runners.

Run through redwood groves on winding single track trails in the Santa Cruz Mountains at Summit Rock, a scenic trail race just outside Silicon Valley. Half marathon, 10K and 5K distances welcome walkers and hikers with a separate hiker star..

Run a scenic, challenging loop around Angel Island with sweeping views of the Golden Gate, Alcatraz and San Francisco. Choose the half marathon or 10K and ride the chartered ferry to this intimate 400 runner event.

Run scenic trails at Huddart County Park on Dec 20, 2025 with distances from 10K to 50K to suit every trail runner. Marked courses and stocked aid stations help on technical singletrack; bring a reusable cup for the cupless race.

Ring out the year with Almost New Year's Eve at scenic Lake Chabot in Castro Valley on 12/27/25. Trail routes for runners, walkers and hikers include 5K, 10K and half marathon distances with free post race photos.