Trail Running calendar near Charleston 2026-2027

A winter trail 3.1 mile race at Willenborg Woods near Charleston, IL, with steep climbs and over 900 feet of elevation gain. The course is fully marked, includes a stream crossing, and recommends trail shoes and warm layers.

Trail races in Owen Putnam State Forest feature single track looped courses in 50 mile, 50K, 14 mile and 10K distances. The event is organized by the Indiana Trail Running Association and is a cupless race with limited camping.

A trail event at Hawthorn Park offering a 5 mile run, 4 mile walk and 1 mile fun run, with marked trails, volunteer support, awards and a post-race breakfast taco bar. Preregistration is required by April 12 for a shirt.

Clinton Lake Ultra on March 28, 2026 in DeWitt, IL features a 30 mile and a 10 mile trail race on three 10 mile loops, two aid stations per loop, mandatory volunteer service, race awards, and event swag.

A weekend of in-person and virtual races in Monticello, Illinois, featuring a trail and road Half Marathon, 10K, and a nighttime Trail-Glo 5K. The event benefits Robert Allerton Park and supports Make-A-Wish Illinois.

The DINO Trail Run returns to DePauw Nature Park, featuring 5k and 15k courses on crushed stone trails. Runners can enjoy views of the park's rock quarry cliffs on a route with mostly gentle grades and a few steep hills.

A cross country 5K across grass and campus trails at Lincoln Trail College plus a one mile kids run around the pond and through the woods. Awards include top male and female prizes and age group medals.

A 7.1 mile trail run around Lake Mingo at Kennekuk Cove County Park on June 13, 2026. The mostly trail course features hills, nine bridges, one aid station halfway and a post race party at the Hideaway Shelter.

Get ready for a wild summer 5K where the course sends you splashing down the middle of the Embarras River. With only 125 spots, this intimate trail race finishes with a steep hill climb and a fun post-race pancake and ice cream party.

A 10k trail race at Griffin Bike Park in Terre Haute on August 1, 2026. The two lap course circles Stryker Lake with rolling hills and generally stable footing; finishers earn bonus series points based on placement.

A trail-focused running event at Kickapoo State Recreation Area on September 12, 2026, offering a 5K and a mostly-trail 7.45 mile course with aid stations, on-site packet pickup, awards, and a post-race gathering with food.

Trail runners in Decatur can choose between 4.4 and 7.6 mile courses on the fast rolling terrain of the Sand Creek Conservation District. Registration includes a tech shirt and finisher medal, with race proceeds supporting the Special Opera..

This trail run/walk in Greenville's Patriot's Park is a 5K event supporting childhood cancer research. It takes place on scenic trails and is inspired by a personal story of courage.

Trail races at Willenborg Woods near Charleston, Illinois on October 16 and 17, 2026. Multiple distances from 5K to 100K on marked single-track trails with riverside sections, creeks, hills, volunteer support and a post race celebration.

A trail event at Robert Allerton Park in Monticello on October 25, 2026, featuring a 5.7 mile run, a 2 mile nature walk, and a virtual 5.7 mile option. A portion of proceeds supports park trail maintenance and improvements.