Trail Running calendar near Oakwood 2026-2027

Camp Tecumseh’s tenth annual Running with Raccoons 5K takes place April 26, 2026 in Brookston, Indiana. This chip timed run/walk raises funds for the campership fund and follows a scenic route through camp grounds.

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 Second Wind Running Club event on May 9, 2026, the Buffalo Trace Trail Race follows an approximately 5-mile course through woods and prairie at Lake of the Woods; registration is available online and proceeds benefit the Forest Preserve F..

The Big 4 Trail High-Five Classic is a trail run on the paved Big 4 Trail in Lebanon, Indiana. Choose from 4, 8, or 12 mile distances on an out-and-back course. The event features a community atmosphere and a post-race celebration.

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 mile trail race through wooded routes at the Vigo County Conservation Club in Terre Haute, Indiana. Registration runs from April 1 to May 23 and the entry 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.

Five Thursday nights in July at Maxwell Park in Normal, IL featuring 800 meter, 2 mile and 3 mile cross country races. Weekly entry is $5 or $20 for all five nights; awards night with age-group prizes is on 7/30.

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..

A women only 5K obstacle mud run at Wildcat Creek MX in Rossville, IN on August 9, 2026. The course includes 18 plus obstacles and welcomes females age seven and older to run, jog or walk in a noncompetitive, team focused setting.

A youth and family 2K obstacle course at Maxwell Park with about 15 obstacles. Waves serve ages 5 and up; participants get a shirt, medal and a timed result, with trophies for top three in each competitive age group.

Hill of a Race 2026 in Bloomington, IL combines a lap based Endurance Challenge with multiple 3 mile obstacle course waves, including competitive men, women, masters and several recreational waves.

Test your endurance at Comlara Park with a unique hourly trail challenge ranging from one to twelve hours. Run a scenic loop every hour to stay in the game or enjoy a relaxed pace in the open format events.