Trail Running calendar near Madison 2025-2026

Take on scenic, technical trails at the Mines of Spain Trail Races in Dubuque, IA on August 8, 2026, with 4 mile, 7 mile and half marathon options. Enjoy bluff views of the Mississippi, challenging climbs and a family friendly kids mini rac..

Push your limits at Run The Hawk Trail Run in Middleton, WI, a timed challenge at Blackhawk Ski Club. Solo or team multi hour races and a fun run on a rugged loop with steep climbs, pines, a spring pool and a ski jump backdrop.

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..

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.

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.

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.

Explore rugged, scenic trails along the Mississippi at the Mines of Spain 100 in Dubuque on October 16, 2026. Choose 100 mile or 100K on a roughly 20 mile loop through prairies, hardwood forests and technical climbs.

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 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.