Trail Running calendar near Middleton 2026-2027

Run the Whitewalker Ultra 100k in Palmyra WI on January 17 to 18 2026, a winter trail challenge of two 50k loops from Emma Carlin campground across the Ice Age and Scuppernong trails. Limited spots remain so register by January 16.

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.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

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..

Lace up for the Galena Classic Sasquatch Shuffle, a festive 3k snowshoe run or walk at Eagle Ridge on February 14, 2026. Event goes on with or without snow, rentals available and awards for top finishers in multiple divisions.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

Tour de Dodge is a scenic trail running festival at Governor Dodge State Park with 50K, 27K and 10K routes on March 7, 2026. Proceeds benefit local conservation and runners enjoy stocked aid stations, a custom shoe bag and horseshoe finishe..

Run with your dog through scenic wooded single track at Lake Geneva Ziplines, choosing a 4 mile loop or an 8 mile double lap. This friendly canicross event offers water at the start area, prizes for top teams, and a finisher token.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

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..

Run the Donald Dash Trail Run at Donald County Park in Mount Horeb on May 2, 2026 for scenic prairie, sandy and hilly single track trails and distances of 5 km, 15 km and a Kids One Mile Fun Run. All net 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.

A trail event in Delafield, Wisconsin offering half marathon, 10K, 5K, ruck options and a Kiddos 1K; proceeds benefit Tall Pines Conservancy and courses use marked park trails.

Run the Sugar Badger 50/50 and Half in Belleville WI with 50M, 50K and half marathon options on flat, scenic Badger and Sugar River trails with trestles and a short tunnel. Aid, free photos, pizza and beer await finishers.

Kettle Moraine Ultramarathon in La Grange WI on June 13 and 14, 2026 showcases rugged, scenic trails with about 65 miles on the Ice Age Trail. Distances from 38 to 100 mile plus 100K and a 4 person relay; 100 mile offers a Western States qu..

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.

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.

Run scenic bluffs and Mississippi River views at the Mines of Spain Trail Races in Dubuque, featuring half marathon, 7 mile and 4 mile course options. Expect technical mixed terrain, aid stations, and a free kids Mini Mines during packet pi..

Run The Hawk at Blackhawk Ski Club in Middleton, WI on August 22 invites runners to chase laps on a rolling 2.25 mile loop in 3, 6, or 12 hour timed events, or enjoy the shorter Fun Run. Mixed trail surfaces, a steep climb, and team relay o..