Trail Running calendar near Roscoe 2026-2027

A point to point, all trail ultramarathon along the Hennepin Canal State Trail in northwest Illinois. Multiple distances from 50K to 100 miles, with aid stations every 3 to 7 miles and a 30 hour cutoff for Western States qualification.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

A fall event at Zachariah's Acres in Oconomowoc that raises funds for children with special needs. Routes include a half marathon, two 5K options including ruck, and a one mile family walk and roll through prairie and woodland scenery.

Trail loops at Bethel Horizons near Dodgeville WI with three distances, varied singletrack and ridge terrain, stocked aid stations, and awards plus a tech shirt and medal.

A flat, fast trail event at Half Day Forest Preserve offering Half Marathon, Marathon, 50K and 50 Mile distances on crushed gravel through forests and wetlands with aid stations, finisher medals and the Marathon as a Boston qualifier.

A seven-race trail series in Oconomowoc from April to October 2026 offering 5K, 10K, half-marathon, walking and ruck options, cupless events, age-group scoring and finisher Woodles.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

A 5k trail event in Pingree Grove, Illinois on October 23, 2026 where participants can run, walk, or ruck through a course with haunted sets, animatronics, and actors. The evening includes multiple heats plus a costume contest, bonfire, ent..

Trail ultraruns of 25K and 50K on a 5.5 mile loop at Red Gate Woods near Willow Springs. Mostly single track with staffed aid stations and a 5pm cutoff; no pacers allowed.

A trail race at The Forge in Lemont, IL on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double track trails with variable surfaces, an aid station for multi-lap races, and a 400-runner cap.