Trail Running calendar near Rockford 2025-2026

Run rolling prairie, single track and sandy hills at the Donald Dash in Donald County Park near Mount Horeb, WI. Choose 5 km or 15 km and support Friends of Donald Park as proceeds fund trail upkeep.

Run scenic trails at Teason's Woods in Palos Hills on May 9, 2026 with marathon or 10 Mile options over rolling terrain and shared two way trails. Enjoy event apparel, a wooden sunflower medal for finishers, plus post race chili and beer.

Join the Sugar Badger 50/50 and Half in Belleville, WI for flat, scenic out and back runs on the Badger State and Sugar River State Trails with 50 mile, 50K and half marathon options. Expect trestle bridges, a quarter mile tunnel, aid stati..

Kettle Moraine returns June 13 and 14 2026 in LaGrange Wisconsin, offering 100 mile, 100K and shorter trail distances with plenty of Ice Age Trail scenery. The 100 mile serves as a Western States qualifier, making this a prime summer ultra.

Run the scenic Ice Age Trail at the Whitewater Trail Challenge in Whitewater Wisconsin on June 20, 2026. Pick 50K, half marathon or 10K courses that mix smooth singletrack and technical footing for a rewarding trail day.

Tackle rugged trails at the GristMill Grind in Franklin Creek State Natural Area, featuring 5K and 10K routes with creek crossings, bluffs and forest canopy. All proceeds support Franklin Creek conservation and park improvements.

The Echo 136 is a 136 mile trail ultramarathon through the scenic Kettle Moraine and Ice Age State Trail near Whitewater, Wisconsin on September 25, 2026. Expect rugged singletrack, generous aid stations and a 55 hour time limit.

Run the scenic 104 mile Hennepin Canal State Trail from Sterling to Colona on a flat and fast all trail course. Choose 100 mile relay, 50 mile, or Mule 50K night run and earn memorable finish swag.

Take in wooded trail views at the Fall Into Fall Trail 5k in Janesville, then stay for live music, food trucks and beer and wine tasting at the festival. Run or walk a fun, scenic course and celebrate the season with community festivities.

Join the Haunted Highlander Assault Trail Run on October 3 for a spooky 5K through forest trails with haunted sets, animatronics and actors. Run, walk or ruck, then enjoy a costume contest, bonfire, live music and food.

Enjoy a fall run, walk and roll through 125 acres of prairie, ponds and fall color at Zachariah's Acres in Oconomowoc. Choose 5K, half marathon or a family one mile loop while supporting nature based programs for children with special needs..

Join the Jaimie Cox Memorial Run in Roscoe IL on October 17, 2026 for a family friendly 5K or 2 mile walk along the scenic Stone Bridge Trail. Run for a cause as proceeds support the Jaimie Cox Memorial Scholarship.