Trail Running calendar near Middleton 2025-2026

Take on the Whitewalker Ultra 100k at Emma Carlin in Palmyra WI on Jan 17 and 18, 2026, with two scenic 50k loops through Ice Age and Scuppernong trails. Enjoy staffed aid stations and 24 hours to finish this memorable winter trail challeng..

Brave winter trails in Dubuque County at the Triple D Winter Endurance Race, featuring bike and run distances from 5K to 70 miles on the Heritage Trail and nearby routes. Finish at 7Hills for warm food, prizes and community celebration.

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

On February 7, 2026 join the Frozen Assets 5K in Madison and run or skate across the frozen surface of Lake Mendota, starting and finishing at The Edgewater. Enjoy scenic views of downtown and the UW Madison campus during the Frozen Assets..

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

Run scenic Driftless trails at Governor Dodge State Park on March 7, 2026, choosing from 10K, 27K, or rugged 50K courses. Support local conservation while enjoying stocked aid stations, a custom Silo bag and a horseshoe finisher medal.

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

Trailbreaker in Waukesha invites runners to scenic courses along Glacial Drumlin and Fox River trails, with distances from marathon to Kids 1K. New ruck events add variety while proceeds support local parks and the urban forest.

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..

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..

Part of the Iowa Trail Run Series, Mines of Spain in Dubuque offers 5K, 10K and half marathon trail options on Saturday May 2, 2026. Expect marked courses, rotating race swag, optional tech shirt and tasty post race food.

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..

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..

Hit scenic Ice Age Trail terrain in Whitewater Wisconsin with 10K, Half Marathon and 50K options across rolling, sometimes technical trails. Pick a distance for a relaxed summer challenge or a rugged ultra with great views.

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 the ice age terrain of Devil's Lake at Dances with Dirt, with distances from 10K to 50 miles for every trail runner. Enjoy marked courses with aid, a famously dramatic aid station, finisher medals, and post race food and a brew.

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..

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..