Trail Running Calendar Illinois 2026-2027

A looped trail event at Deer Grove Forest Preserve in Palatine, IL offering 10K, 25K, 50K and 50 mile distances on mostly wide, non-technical trails with a single aid station at the start and finish.

Experience a bib timed run through the natural twists and turns of Saw Wee Kee Park. Join this spring event to earn a unique medal piece and enjoy the changing seasonal terrain in Yorkville.

Run or walk to support Anderson Humane at their largest fundraiser. Choose a timed 5K run or bring your dog for a 1.5-mile walk along the Batavia Riverwalk. The event includes awards, a lure course, and activities for animal lovers.

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

The Hearts Desire 6-Hour Endurance Run in Herrin is a timed event where runners complete as many 1.3-mile paved loops as possible. All participants get a t-shirt, and awards are given for the most loops completed. Refreshments are available..

Experience the Three Ravines Course at Wolf Road Woods with distance options of 3.1 or 5.4 miles. This family friendly trail event features a mix of single track terrain and a post race celebration with craft brews.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

IVS Spring Stampede offers 5k and 10k trail races at Wildlife Prairie Park on May 3, 2026. Park admission is included and the event features water stations, post race snacks, and awards for overall and age group finishers.

A trail marathon and a 10 mile race at Teason's Woods on May 9, 2026, run on the Sag Valley Trail. Wide horse trails, notable elevation, multiple aid stations, sunflower-themed shirts and wooden finisher sunflowers.

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..

Timed loop trail events at Chestnut Mountain Resort in Galena Illinois offering 8 hour and 4 hour formats, scenic Mississippi River views toward Iowa and Wisconsin, and an evening finisher meal at the resort.

A timed endurance trail event near Willow Springs on a 4 mile loop with single and double track, rolling hills, a signature aid station offering snacks and drinks, and a mandatory reusable cup policy.

Operation GRANITE X at Tri-Township Park on May 16, 2026 features 6 mile loops made of three two mile laps. Two divisions are offered, one with escalating weight and one focused on endurance.

A chip timed 10K through mostly crushed limestone trails and wooded scenery at The Forge Lemont Quarries near Lemont, IL. Part of the Chicago Racing Circuit with overall and age group awards and a 450 runner capacity.

Frontline OCR at Byron Motosports Park on May 23, 2026 offers 10K and 5K obstacle courses, a ruck division, a kids mile, Special Forces and Heroes waves, plus team entry packs, organized by a 501(c)(3) foundation.

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.

Experience the historic landscapes of Springfield at the Lincoln Memorial Garden Trail Race 8K. Run through scenic lakeside trails and prairie grounds followed by a medallion finish and post race refreshments.

Trail races at Giant City State Park include a new 5k, a half marathon loop, and a 40k two loop option on mostly single track with creek crossings, aid stations, cupless format, and optional t shirts.

Join the free Dirt Circus community running festival in Crystal Lake on May 30, 2026. Choose between a 4.3-mile or 6.8-mile social group run, then enjoy a festival with food, an expo of local brands, and a raffle. Meet race directors and co..