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Trail Running calendar near Cupertino 2026-2027

We have found 86 Trailruns within 80 miles of Cupertino. See below where and when you can find the races.

Brazen New Year's Day

Castro Valley - 26 mi from Cupertino

Start the new year with a run at Lake Chabot in Castro Valley. Choose from a half marathon, 10K, or 5K on January 1st. This event is part of the Brazen Ultra Half Series, offering a trail challenge.

Crystal Springs (Winter) Trail Run

Woodside - 14 mi from Cupertino

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Explore the redwood trails of Huddart Park across distances from 8K to 50K. The routes offer varied terrain and significant elevation gain, with full aid station support. All finishers receive a custom medal in this cupless event.

Coyote Hills Run

Fremont - 15 mi from Cupertino

Run or walk scenic bay trails at Coyote Hills Regional Park. Choose from three distances: half marathon, 10K, or 5K on a course with minimal climbing. Aid stations are available, and a Hiker Division is offered for walkers.