Madison

Trail Running Calendar near Madison 2026-2027

Explore the top trail runs near Madison for 2026-2027! We've gathered 3 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

Trail Running Calendar United States

October 2026

Oct

Belhaven Hills Classic

Jackson | 11 mi from Madison

Road Race Trail Run 8 km 16 km

A fourth annual road and trail event in Jackson MS offering races from 1 mile youth runs to a 16k across Belhaven and nearby trails.

November 2026

Nov

Race 2 Home

Hinds County | 20 mi from Madison

Trail Run 3 mi

A charity 5K in Jackson, MS on November 14, 2026 organized by the St. Dudes Baseball team to raise funds for pediatric cancer research, treatment, and family care.

February 2027

Feb

Frosty 15

Madison

Trail Run 15 km 16 mi

Out and back trail race on the Yockanookany section of the Natchez Trace near Madison MS, offering 15.5 mile and 15K routes with aid stations and cupless rules.