Trail Running calendar near Willow Springs 2026-2027

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.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

Soul Crusher is a trail race in Crystal Lake, IL offering 10 mile and 5 mile options on single track forest trails with looped sections and occasional extra mileage. Packet pickup is available the day before and a 3 hour 30 minute cutoff ap..

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 event at Deer Grove Forest Preserve offering 50K, 25K and a 5 mile option on mostly single track loops, with stocked aid stations, marked maps and an emphasis on whimsy and inclusion.

Howl-o-ween 5k at Busse Woods is a themed run and walk supporting animal shelters; the chip timed 5k welcomes dogs without separate registration and includes a shirt and finisher medal.

A nighttime run and walk at Lake County Fairgrounds on October 30, 2026 featuring a timed 5K, a non-timed 2K, a market with live performances, costume contests, and awards.

A trail running event at Camp Big Timber in Elgin, IL on November 8, 2026 offering 3 mile and 5 mile courses plus a Kids Fun Run. The course includes grass, gravel and a creek crossing and supports local youth organizations.

A half trail run at Stoney Run County Park on November 14, 2026, held over two loops across grass, pavement, gravel and single-track trails, with aid stations, on-site packet pick-up, a raffle and informal timing using popsicle-stick finish..

Late November trail festival in Lemont IL offering 10K, 20K, 30K and 60K on single and double track and gravel around historic quarries and the I&M Canal. Courses start and finish at The Forge and use lap formats.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A Canicross-focused trail event at Lake Geneva Ziplines and Adventures offering one 4-mile loop or two loops for 8 miles, dog-powered and dog-friendly options, awards for dog teams, on-course drinks but bring a refillable vessel.

A winter obstacle event in Lake Geneva on January 30, 2027 offering distances from a kids course to a 20K Yeti Challenge, plus a competitive Elite division with cash prizes, team entries, and a virtual race option.

Woodsy single track races in March 2027 at Soldiers Memorial Park, LaPorte, IN. Distances are a 10K and a half marathon over winding, not flat trails; aid stations are about every 2.5 miles and the event is cupless.

Trail races at The Forge take runners through wooded single and double track trails around the Lemont Quarries. The event offers a trail half and a quarter marathon with variable terrain, one aid station for the half, and chip timed results..

Childish Nonsense in Deer Grove Forest Preserve, Palatine IL on April 24, 2027 features looped trail races from 5.5 miles to 50 miles. One aid station at the start/finish is available every 5.5 miles and pacers are allowed for 50 milers aft..