Trail Running calendar near Joliet 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..

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.

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.

Trail race in Crystal Lake, IL on October 17, 2026 offering 5 Miler and 10 Miler options on single track trails with bonus mileage. Carry your own hydration; finishers receive a race shirt and a skeleton medal.

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 looped trail event offering 50K, 25K, and a 5-mile option on mostly single-track terrain with staffed aid stations and an organizer focus on community and inclusion.

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 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 event at Camp Big Timber on November 8, 2026 featuring 3- and 5-mile perimeter loops plus a kids fun run. The course includes grass, gravel, a creek crossing and a post-race pancake breakfast for all participants.

A two-loop trail run at Stoney Run County Park on November 14, 2026, over mixed surfaces with on-course aid stations. Packet pick-up includes a raffle and memorabilia sales, with proceeds benefiting the park.

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 Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

Experience a cross country style trail race through the Timber Pointe Nature Center at Lake Bloomington. Choose between 4K and 8K loops or a three hour endurance challenge while supporting local nature conservation.

Four winter trail races in Dixon, IL totaling 31 miles, with distances from 5K to 20K on varied terrain. Series prizes include overall standings and age category awards, and registration fees are nonrefundable.

A Canicross focused running event at Lake Geneva Ziplines and Adventures offering a 4 mile loop with an option to do two loops for 8 miles. Dogs may run hands free in Canicross or on a y shaped harness with a handheld leash.

A winter obstacle race at Lake Geneva offering 5K, 10K, a 20K Yeti Challenge, a kids course, team packs and a virtual option. Fun heats allow skipping obstacles while the Elite division requires full obstacle completion for podiums.

Early-season trail races at The Forge in Lemont, Illinois, on wooded single and double track trails with mud, roots and gravel. Distances offered are 13.1 miles and 6.5 miles with technical singletrack sections.