Trail Running calendar near Oakwood 2026-2027

A backyard ultra in Wingate, IN on a 4 miles 880 feet out and back course with mixed gravel, grass, and road surfaces. Loops start one hour apart, each must be completed within the hour, and the last person to finish a loop wins.

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..

Trail running event in Lebanon, Indiana with **4**, **8**, and **12** mile out-and-back courses on paved rail to trail and wooded sections. Inclusive registration offers Male, Female, and Non-Binary categories plus deferral and bib transfer..

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 in Charleston, IL on May 30, 2026 where runners repeat a 4.167 mile trail loop each hour until one finisher earns a Bronze Ticket toward the Big Dog's Backyard Ultra World Championship.

A 3.1 mile cross country 5K across grass and paved paths on the Lincoln Trail College campus, plus a one mile Kid's Fun Run around the pond. Age group medals and overall prizes are listed for the 5K.

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.

A runner-built 4.5 mile loop ultra in a reclaimed limestone quarry offering 6 and 12 hour solo or relay options plus a single 4.5 mile trail run, two aid stations with Tailwind, and support for local youth track programs.

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 summer **5K** at Willenborg Woods in Charleston, IL featuring winding forest trails, a one third mile river crossing through the Embarras River, a steep finish climb called Billy Goat Hill, and a small field limited to 125 participants.

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.

A loop ultrarunning event at Kennekuk Cove County Park with 3.25 mile laps, aid stations, camping, shirts and swag bags, and four hour and eight hour runner and walker options. Field limited to 250 participants.

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.

A day of looped trail events at Comlara near Hudson, IL, with timed options from one hour to twelve hours, a relay race, and an open course option. Runners complete roughly four mile loops and must return each hour to continue.

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.