Trail Running calendar near Chicago 2026-2027

A 3.62-mile all-grass cross-country race at Lovelace Park in Evanston with individual and team entries, tiered entry fees by registration period, a performance shirt with entry, and a post-race awards gathering with food.

Set on the crushed limestone trails of Danada Forest Preserve in Naperville on Sep 5, 2026, this USATF certified event offers a chip timed half marathon and 10K, finisher medals, pacers, live tracking, and shuttle parking from off site lots..

A three day trail event at Rock Cut State Park featuring a night 10 km plus 25 km and 50 km races, with single race entries and Triple Crown series options that award commemorative spike prizes to finishers.

A remembrance event at the Lake County Fairgrounds Grandstand in Crown Pont, IN where participants climb 17 laps totaling 1,980 steps or join a 1 mile non timed walk. The event includes hero wristbands, limited finisher medals, and supports..

A timed urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.

Turbo Trot and Mini Road Race Rally in Geneva combines a 2.5 mile run, a 1 mile kids race, and a battery car rally for ages 3 to 8 at Peck Farm Park. The event raises funds for the Geneva Park District Scholarship Fund.

A one-day trail running festival at Goodenow Grove Nature Preserve in Beecher, IL offering 5K, 10K, 10K RUCK, 20K, 30K and 50K on looped trail courses. The event is cupless with aid stations and provides race shirts, medals, and awards.

An obstacle course race at Indiana Dunes National Park on September 13, 2026, featuring 10k, 5K and a K9 3.1-mile event. The course uses varied landscapes to reflect terrains associated with military service.

Midwest OCR in Marseilles, Illinois features 5K and 10K obstacle courses, ruck options, a kid's loop, and a multi-lap Bearded Challenge, with finisher shirts, medals, and professional photos included; elite divisions award podiums and cash..

A loop-based running event at Limestone Park offering 8 hour and 4 hour races on a 1.65 mile course with mixed crushed limestone and asphalt terrain. Scoring is by completed loops and proceeds support local organizations.

A community road and trail event at Moraine Hills State Park offering 5K, 10K and half marathon distances with in person and virtual options Sept 1 to 27, 2026. Proceeds support the Friends of Moraine Hills State Park.

Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.

A timed 12 hour and 6 hour loop race along the Evanston lakefront with two aid stations, public facilities, handcrafted finisher awards and a finisher beverage from Sketchbook Brewery. Packet pickup is available in Evanston.

A 30 minute run or walk up Mt. Hoy at Blackwell Forest Preserve on September 26, 2026. Entry fees support Bridge Communities to house a family for two years while they work toward self sufficiency.

Backyard Nonsense is a timed trail event at Richard Bong State Recreation Area on September 26, 2026, with 24 hour, 12 hour, 6 hour and 3 hour options including a Backyard 24 format on a 4.1 mile loop. Group campgrounds are reserved and a W..

Multiple trail distances run on a 4 mile loop at Tryon Farm with grassy fields, singletrack and short pavement. Proceeds benefit the Tryon Farm Institute and the event is part of the Crazy Legs Race Series.

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.

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..