Trail Running calendar near Rockford 2025-2026

Take on the Donald Dash Trail Run on May 2, 2026 at Donald County Park in Mount Horeb, WI with scenic 5 km and 15 km options over prairie, single track, sand and hills. Limited to about 300 runners, all proceeds fund Friends of Donald Park..

Run the Great Western Half Marathon and 10K on a flat out and back limestone path along the historic Great Western Trail. Hosted by Fox River Trail Runners, this longtime race supports local mental health charities.

Run scenic horse and forest trails at Teason's Woods on May 9, 2026 with a 26.2 mile marathon or a 10 mile option. Finishers get a wooden medal and can refuel with hot chili and beer.

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..

Run scenic flat trails along the Badger State and Sugar River in Belleville WI at the Sugar Badger 50 Miler, 50K and Half Marathon on May 23, 2026. Enjoy generous cutoffs, stocked aid stations, a quarter mile tunnel so bring a light, plus p..

Celebrate the 25th anniversary 5K for Double "J" in Joliet on June 6, 2026 as participants run the Rock Run Greenway and finish at Cemeno's. Proceeds support the Pat Clark Cancer Foundation and registration includes a T shirt and medal.

Challenge yourself on the scenic Kettle Moraine trails in LaGrange WI with distances from 38 miles to the full 100 miler and team relays. A largely Ice Age Trail course and Western States qualifying time make this a classic ultrarun.

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..

Experience trail running along the scenic Ice Age Trail near Whitewater, Wisconsin, with 50K, half marathon and 10K options. Rolling hills, varied footing and lakeside views make this a rewarding challenge for trail lovers.

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..

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..

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.

Run the GristMill Grind on September 5, 2026 at Franklin Creek State Natural Area, a hilly technical trail offering 5K and 10K routes through ravines, limestone bluffs, springs and creek crossings. Proceeds support park conservation.

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..

Echo 136 is a 136 mile trail ultra through the scenic Southern Unit of Kettle Moraine State Forest near Whitewater, Wisconsin, following the Ice Age State Trail. Runners have 55 hours to tackle varied terrain with stocked aid stations along..

Run the Hennepin Hundred, an all trail ultramarathon along the scenic Hennepin Canal featuring flat terrain and canal and farmland views. Distances: 100, 50, 50K and team relay with Western States qualification for the 100.

Join the Fall into Fall Trail 5k in Janesville on October 3 for a scenic run or walk along tree lined dirt trails. Stick around for the Fall Into Fall Heritage celebration with live music, food trucks and tastings.

Haunted Highlander Assault Trail Run offers a spooky 5k in McHenry, IL with haunted sets, animatronics and actors across timed heats. Stick around for a costume contest, bonfire, live music 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 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..