Winterset
Trail Running Calendar near Winterset 2026-2027
Explore the top trail runs near Winterset for 2026-2027! We've gathered 5 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
An off road 5 miles run through three historic farm sites at Living History Farms on November 7, 2026, with costume contests, awards, a kids run, and a cowbell finisher medal.
4 mile trail run at Goeldner Woods on November 7, 2026, with individual and four person team options, rugged terrain and a postrace pull up time bonus.
A charity 5K and 1 mile fun run in Des Moines on November 14, 2026, held at Confluence Brewing Company. The looped trail event features chip timing and supports Marys Helping Hands, which provides basics for new families.
December 2026
Sycamore 8 is a December trail race in Johnston, Iowa, that follows the Sycamore Trail along the Des Moines River. The route offers rolling single track, river views, variable winter conditions, and a field capped at 300 participants.
April 2027
A community 4K fun run at the Madison County Fairgrounds in Winterset, Iowa, organized by Madison County Youth Council, $20 entry and a shirt guarantee for registrations before March 21.