Trail Running calendar near Charleston 2026-2027

Experience the beautiful trails of Allerton Park in Monticello with a weekend of running events. Choose from a glow in the dark 5k, a 10k, or a half marathon while supporting Make A Wish Illinois.

Experience the scenic rock quarry cliffs of DePauw Nature Park in Greencastle. This event features 15k and 5k trail runs on crushed stone paths with mild grades and a few steep climbs.

A backyard ultra in Wingate, IN on May 9, 2026 where runners repeat a 4 miles 880 feet out and back loop each hour on road, gravel and grass until one runner completes more loops than any other.

A trail race at Lake of the Woods Forest Preserve with an approximately 5 miles course through wooded trails and prairie. Organized by Second Wind Running Club with online registration through race day and proceeds supporting the Forest Pre..

A time based endurance event on a scenic 5K loop offering six hour and twelve hour formats for solo runners, teams, and walkers, with Runners Village, optional camping, live tracking, and post race awards.

A 3.1 miles trail race at the Vigo County Conservation Club in Terre Haute, featuring wooded trails, rolling hills, winding paths, and uneven terrain. Registration opens April 1, 2026; the fee is $30.

A backyard ultra at Willenborg Woods near Charleston, IL, run on a repeating 4.167 mile loop each hour until one runner remains. The final finisher receives a Bronze Ticket tied to a backyard ultra championship.

This cross-country event offers a scenic 5K run through Lincoln Trail College, featuring a mix of grass and paved paths. A shorter Kid's Fun Run is also available on the paved course. Awards are given for overall and age group winners, and..

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.

A family-friendly adventure trail 5k at Griffin Bike Park with obstacles like a floating bridge, race tee and timing chip included, team rebate options, age-group awards and participant rules on strollers, bikes and children.

Run through a scenic reclaimed limestone quarry in Greencastle at the Vulture Vista Ultra. Choose from 6 hour or 12 hour timed events or a single 4.5 mile loop on wooded singletrack and open trails.

A backyard ultra at Quail Ridge Farm in Albion, IL on July 18, 2026. Registration includes a t-shirt and a $10 food truck voucher and free camping is available the night before. A voluntary $1 per lap pool will be split among top finishers.

A 5K trail race at Willenborg Woods featuring a one-third mile river crossing, about 1,100 feet of elevation gain, a steep final climb, limited to 125 runners, with post-race pancakes and ice cream.

A two lap 10 km trail run around Stryker Lake at Griffin Bike Park on August 1, 2026 with rolling hills, generally stable footing, onsite registration, and series bonus points for finishers.

Experience a trail run through Forest Park on the General Dacey Trail in Shelbyville. Participate in a 5K or 1 mile race featuring team competitions, post race refreshments, and a gathering at the local aquatic center.

Event Overview The Howl at the Moon Ultra is a timed endurance event held at Kennekuk Road Runners in Danville, Illinois. The event features separate eight-hour and four-hour divisions for runners and walkers. Course Details Participants co..

Experience the 46th annual trail run through Kickapoo State Recreation Area featuring a scenic pond loop and a longer 95 percent trail course with creek crossings and steep hills.

Experience fast rolling terrain at the Sand Creek Trail Run in Decatur. Choose between 4.4 and 7.6 mile distances to support the Special Operations Warrior Foundation through the scenic Macon County Conservation District.

Conquer a rugged 1200 acre off road course at the Badlands Off Road Park. Choose from 5K, 10K, and 21K obstacle races featuring sand dunes and forest trails for a complete weekend of outdoor adventure.

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.