Trail Running calendar near Monticello 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..

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.

An 8K trail race entirely within Lincoln Memorial Garden near Lake Springfield with wood-chipped and gravel trails and plank bridges. A Kids Fun Run offers three pond-loop distances; the 8K is limited to 300 participants and includes a shir..

Experience the local trail community at Kinsey Park with a four mile loop featuring rolling hills and themed stretches. This event offers a great introduction to the local ultramarathon scene in Peoria.

A backyard ultra at Kinsey Park in Peoria where runners complete a 4.16 mile single track loop each hour until one runner remains. The trail is fully single track with small rolling hills and a Wizard of Oz theme.

A chip timed 5K at Mackinaw Valley Vineyard and Winery on June 14, 2026 with a two lap course over grass and uneven terrain. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine; age group awards and a ch..

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 Fourth of July trail event at Centennial Park in Springfield marking the 250th anniversary of American independence. Offers a 1 mile, 5K, and 10K plus volunteer options and chip timing.

Experience flowing singletrack and deep ravines at Black Partridge Park in Metamora. This five mile trail race features creek crossings and steep climbs through mature Illinois forests.

CMAR Trail Races at Camp Wokanda near Chillicothe, Illinois offers multiple looped and out and back trail distances on wooded singletrack with substantial elevation, staffed aid stations, and time cutoffs for each distance.

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.

Experience the final race of the summer at Farmdale Reservoir in Washington Illinois. This five mile trail run features a mix of prairie woods and singletrack paths through a diverse landscape.

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 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.