Trail Running calendar near Charleston 2024-2025

We have found 7 Trailruns within 80 miles of Charleston. See below where and when you can find the races.

The OPSF 50/50 Trail Race is a popular running event held in Owen-Putnam State Forest, Indiana, organized by the Indiana Trail Running Association. Participants can choose from various distances, including a 50-mile, 50K, 14-mile, and 10K trail race. The course features predominantly single-track tr..

The Clinton Lake Ultra is an exciting trail running event held at the Clinton Lake State Recreation Area in DeWitt, IL. Participants can choose between a challenging 30-mile or a 10-mile race, both featuring scenic loops through forests, hills, and meadows. The event emphasizes sustainability by enc..

April 2025

The Allerton Races is a running event taking place in Monticello, Illinois, featuring a variety of races including a Half Marathon, 10K, and a nighttime Trail-Glo 5K. Participants can also choose virtual options for the Half Marathon, 10K, and 5K. This event supports Robert Allerton Park and encoura..

The Grind on the Grid Backyard Ultra is a unique running event held in Veedersburg, Indiana, designed for endurance athletes. Participants run a 4-mile loop that includes a mix of gravel, grass, and road surfaces, with the goal of completing as many loops as possible within an hour. The event emphas..

May 2025

The Elsa Chicken Plucker Backyard Ultra is an official Backyard Ultra event held in Charleston, IL. Participants will run a 4.167-mile loop every hour, continuing until only one runner remains. The course features groomed grass and dirt trails during the day, while the night loop includes a dead-end..

September 2025

The Kennekuk Road Runners - Wild Wild Wilderness is an annual running event held at Kickapoo State Recreation Area in Oakwood, Illinois. Celebrating its 45th year, the event features multiple races, including a 5K, a 7.45-mile trail run, and the WWW Challenge. Participants can enjoy a scenic and cha..

October 2025

The Shake Your Trail Feather Trail Run offers a variety of challenging race options, including a 5K, 10K, half marathon (13.1 miles), and a 50K. Set in Charleston, IL, participants can enjoy beautiful grass and dirt trails, pristine timber, and a creek crossing, all while navigating hills and valley..