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Trail Running Calendar near Woodside 2026-2027

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Explore the top trail runs near Woodside for 2026-2027! We've gathered 62 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

May 2027
May
22
Sa

Run for Amma

Trail Run Walk 10 km 30 km 50 km
Charity trail event at Skyline Ridge Open Space Preserve offering 50K, 30K and 10K with all registration proceeds donated to UCSF cancer research.
May
29
Sa

Beer City Half San Jose

Road Race Trail Run Walk 5 km 10 km Half Marathon
Beer City Half San Jose on May 29, 2027 at Almaden Lake Park pairs trail and park running with a beer festival. Events include a half marathon, 10k, 5k, a 1 mile Beer Stroll, the Beat the Beast beer mile, and beer tastings.
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