Trail Running calendar near St. Charles 2026-2027

Emmy's Rustic Run is a Fort Atkinson trail run and family fun day raising funds for the A-T Children's Project, featuring a 5k, a one mile walk, kids races and virtual participation.

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..

Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.

A multi distance trail event at Tryon Farm in Michigan City on October 3, 2026. Runners complete laps of a 4 mile loop over grassy fields, single track trails and short paved sections, with proceeds benefiting the Tryon Farm Institute.

Point-to-point, all-trail ultramarathon along the Hennepin Canal between Sterling and Colona, Illinois, offering 100 mile, 50 mile, 50K and team relay options with regular aid stations and finisher awards.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

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 fall trail event at Lapham Peak State Forest featuring timed 5K and 10K runs, accessible walk options, and a free 1K Smokey Bear run for children age 10 and under; participant shirts, awards, and post-event treats are included.

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.

Timed ultraruns in Southern Kettle Moraine Forest on Oct 10 to Oct 11, 2026. Solo runners or teams of up to four complete as many 3, 5, or 6 mile McMiller Trail loops as possible in 6, 12 or 20 hour formats.

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.

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 race in Crystal Lake through Veteran Acres and Sternes Woods with 5 and 10 mile options, packet pickup on Friday and race morning, cup-less course, and finishers' medals and shirts provided.

A fall event at Richardson Adventure Farm in Spring Grove on October 18, 2026 featuring a 10K, two 5K options including a corn maze route, a 1-mile family adventure, chip timing, and a finisher medal for every participant.

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.