Shake Your Trail Feather Trail Run

Shake Your Trail Feather Trail Run is held in Charleston, Illinois, on October 17, 2026. The 50K (31 miles) and the 16-mile race (25.7 km) start at 8 a.m., and the 8-mile (12.9 km) and 5K follow at 10 a.m. Four distances on one morning make this an easy day to bring a mixed-ability group to.

Central Illinois trail running is generally rolling rather than mountainous, which means the running stays honest: you can hold a rhythm most of the way, so pacing discipline matters more than climbing strength. The 5K and 8-mile suit a first venture off the road, the 16-mile is a solid target for a half marathoner ready for more, and the 50K works as a first ultra after a 16-week build with long runs reaching four hours and a tested fueling routine.