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Trail Running Calendar near Madison 2026-2027

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Explore the top trail runs near Madison for 2026-2027! We've gathered 4 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
10
Sa

Belhaven Hills Classic

Road Race Trail Run 8 km 16 km
Belhaven Hills Classic on October 10, 2026 offers 16k and 8k road and trail races plus 1 mile Kid's and Adult Bier runs through Greater Belhaven.
November 2026
Nov
14
Sa

Race 2 Home

Trail Run 3 mi
5K fundraiser in Jackson, MS at MC Choctaw Trails supporting pediatric cancer research and care, organized by the St. Dudes baseball team on November 14, 2026.
December 2026
Dec
5
Sa

Rolling Hill Revival

Trail Run 7 mi 14 mi
Trail races at Roosevelt State Park offering 7-mile and 14-mile single-track courses with race awards and proceeds supporting park programs.
February 2027
Feb
13
Sa

Frosty 15

Trail Run 15 km 16 mi
Trail races of 15.5 miles and 15K on the Yockanookany section of the Natchez Trace in Madison, MS, with two aid stations and chip timing.
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