Trail Running calendar near Cupertino 2025-2026

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.

Start the year on scenic Lake Chabot trails with Brazen New Year's Day, offering half marathon, 10K, 5K and virtual options with timed results and free photos. Celebrate challenging trail miles and earn a commemorative medal.

Enjoy Bay Area views and varied singletrack at Hacienda Hills Trail Run Winter near San Jose on Jan 3, 2026. Choose from nine distances up to 50K, enjoy marked courses, aid stations and a finisher medal.

Join Hope in Every Step 5K in Modesto, California on January 10, 2026 for a scenic run and walk along the Tuolumne River Parkway trails. Enjoy community vibes, teal race shirts, and friendly competition with awards for top finishers.

Take on scenic, well marked trails at Huddart Park with distances from 8K to 50K plus a free kids dash. Stocked aid stations, custom finisher medals and challenging climbs make this a rewarding trail day for all abilities.

Run through redwood lined trails at Huddart Park in the Crystal Springs Trail Run, with distances from 8K to 50K plus a free kids sprint. Enjoy scenic single track, frequent aid stations and a commemorative finisher medal.

Take on the Pacifica Foothills Trail Run on January 24, 2026 at San Pedro Valley County Park. Choose 30K, half marathon or 10K across Montara Mountain single track for rugged coastal views, chip timed results and well stocked aid stations.

Enjoy scenic trails and marsh boardwalks at Coyote Hills Regional Park in Fremont on January 31, 2026, with 5K, 10K and half marathon options. Updated courses, friendly aid stations and a hiker division make this a welcoming race for every..

Run scenic, rugged trails around Mt. Umunhum at Almaden Quicksilver Park with distances from a mile and kids run up to 50K. Clearly marked courses, aid stations and medals for all finishers make this winter trail event welcoming to all.

Run the Monterey Ultra 50 Miler along Fort Ord and Laguna Seca trails near Monterey, CA. This scenic but challenging 50.7 mile course mixes sandy, rocky and coastal single track with big climbs for an unforgettable ultrarunning test.

Take on scenic dirt trails at Fort Ord and Laguna Seca near Monterey on Feb 7, 2026 with 50K, 25K and 10K options over rolling dunes and late climbs. Aid stations and finish medals await; this is a cupless event so bring a reusable bottle.

Run scenic coastal trails in the Marin Headlands at the Golden Gate Trail Run in Sausalito offering distances from 8K to 50K plus a kids dash. Expect rugged views, stocked aid stations and finisher medals for all.

Bay Breeze invites runners to a scenic, mostly flat bayside course at San Leandro Marina Park on February 14, 2026, with a half marathon, 10K and 5K. Expect chip timing, finisher medals and shirts, stocked aid stations and free race photos.

On February 21, 2026, take on scenic singletrack and fire road loops at Lake Chabot with distances from 5K to 50K for runners of all abilities. Well stocked aid stations and professional timing make this a welcoming, small field trail chall..

Take on the Montara Mountain Trail Run in Pacifica with distances from 10K to 50K plus a kids dash for ages 6 and under. Marked trails, finisher medals, preregistered shirts, and stocked aid stations promise a memorable day on the trail.

Experience panoramic Bay views on the hilly trails of Angel Island with 5, 10, and 15 mile options and a free kids dash. Finishers earn custom medals and pre registered runners receive shirts; a charter ferry from Tiburon is required.

Enjoy scenic ridgeline trails in La Honda CA with 50K, half marathon and 10K courses through redwood forests and open grasslands. All entry fees support Ridge Trail Organisation and every runner receives a Bay Area Ridge Trail duffel bag.

Tackle scenic trails at China Camp State Park in March 2026 with in person or virtual 5K, 10K, and a challenging half marathon. All entrants receive a beer sampler stein, event shirt, and handcrafted woodallion.

Experience the Marin Ultra Challenge on March 14, 2026, a scenic trail run from Rodeo Beach through Mt Tam and Muir Woods with 50 mile and 50K options. Expect rugged single track, redwood canopy and coastal views for a bold trail challenge.

Run three scenic courses over three days in Marin County, summiting classic peaks with sweeping Bay Area views. Choose from 28K and 50K single loops or a new 100K point to point, with full race support, timing and finisher awards.