Trail Running calendar near Pingree Grove 2026-2027

Enjoy a scenic fall run, walk and roll through 125 acres of wooded trails, meadows and ponds. Choose a half marathon, 5K, 5K ruck or family one mile loop and support Zachariah's Acres for children with special needs.

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.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

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 themed 5k trail event in Pingree Grove featuring multiple heats, haunted sets, animatronics, actors, and post-run activities such as a costume contest, bonfire, live entertainment and food. Entry is listed at $50 per heat.

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.

Light up the night at Witches in the Woods 5K/2K in Crown Point. Choose a timed 5K run or a fun 2K walk, enjoy costumes, live music, treats and a family friendly market among the fairground trees.

A trail festival in Lemont, Illinois on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double-track trails around the Lemont Quarries and the I&M Canal.