Trail Running calendar near Yorkville 2026-2027

Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.

A community trail event in Valparaiso with a single-loop 5K and a two-loop 30K team relay hosted by local firefighters, featuring chip timing, aid stations, and team results.

The Lockport Fire Foundation presents the second annual Fire Zone 5k, a community 5k run and walk on a marked loop of the Forest Preserve trail starting at Hassert Park. Registered participants present on race day receive a t shirt and fini..

A community 5K in Flossmoor with a parallel virtual 5K that raises funds and collects goods to support local families experiencing hidden homelessness and provide school supplies for homeless children.

Trail races on the flat, crushed gravel Des Plaines River Trail in Lake County offering Half Marathon, Marathon, 50K and 50 Mile distances.

A 5K timed race and an untimed 2K through the hilly 144-acre Camp Triangle Hills at Crossroads YMCA, held as part of Fall Fest with family activities like rock climbing, archery, tractor rides and a petting zoo.

Trail run at Saw Wee Kee Park on October 17, 2026, over soft, twisting trails with variable footing. Bib-timed waves, part of a four-race series with collectible medal pieces and seasonal swag.

Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.

Trail races of about 5 miles and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with race shirts and finisher medals, a cup-less format, and a 3 hour 30 minute cutoff.

Runs at Richardson Adventure Farm in Spring Grove include a 10K, two 5K options and a 1 mile Family Adventure Run through a corn maze with themed finisher medals and farm attractions.

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

A trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

A Halloween themed nighttime run and walk at Lake County Fairgrounds in Crown Point on October 30, 2026. The event features a 5K and a non timed shorter course, costume prizes, awards, and entry to the Hometown Hocus Pocus Market.

Trail races at Camp Big Timber in Elgin offering 3 mile and 5 mile perimeter loops, a creek crossing, a kids fun run, participant shirt and pancake breakfast.

A 3-mile cross-country race at the MacNider course in Schaumburg on November 8, 2026, with separate women's and men's races, optional team scoring, pre-race packet pickup, and a $25 registration fee.

A half trail run at Stoney Run County Park in Hebron on November 14, 2026, over mixed terrain with two loops, aid stations, raffle and popsicle stick timing.

A trail festival in Lemont on November 14, 2026, offering 10K, 20K, 30K and 60K on single and double-track trails and gravel around the Lemont Quarries and I&M Canal, with multi-lap courses and variable terrain.

On 11/14/2026 the Abominable Trail Race at Lake Geneva Ziplines & Adventures offers 5K, 10K, 15K and 30K courses plus 2, 3 or 4 person 30K relays on forest trails, with water stations, race shirt, finisher medal and free action photos.

Celebrate Thanksgiving with a 2 mile run through the wooded trails of Sheffield Illinois. Wear your best holiday costume for a chance to win prizes at this untimed community event.