Trail Running calendar near Aurora 2025-2026

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.

Take on rolling hills and changing trail footing along a scenic Ice Age Trail section at Rice Lake Nature Trail in Whitewater, WI on June 20, 2026. Choose 10K, half marathon or 50K for a rewarding summer trail challenge.

Join DBC Gifts of Love Community 5K in Flossmoor on June 20, 2026, for a scenic 5K at Vollmer Road Grove Forest Preserve or run the Virtual 5K. Help send backpacks, school supplies and gift cards to local homeless students.

Run the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K or 10M loop courses and relay teams. Unique golf style scoring by Hole turns every loop into a strategic race that rewards speed and smart pacing.

Tackle scenic single track and winding trails at the Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 4, 9, and 18 mile options. Enjoy creek crossings, farmland views and a friendly post race gathering for all finishers.

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 scenic loops through Tryon Farm's grassy fields and single track trails while supporting the Tryon Farm Institute. Choose distances from a 2 mile fun run up to a challenging 50k in this inclusive Crazy Legs Race Series event.

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 in McHenry on October 3, 2026 for spooky 5 km heats through haunted sets and animatronics. After the run enjoy a costume contest, bonfire, live entertainment and food.

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.

Run the Forge Trail Run Festival in Lemont Illinois on November 14, 2026 offering 10K, 20K Half Marathon, 30K and 60K distances. Single and double track plus gravel around the quarries and canal deliver varied, scenic and technical trails.