Trail Running calendar near Iola 2026-2027

Join the Maple Syrup 5K at Brown County Reforestation Camp for a scenic early spring run through woods and gentle hills, perfect for runners, walkers, and families. Kids can try the Mini Maple fun run and everyone is welcome to a post race..

Take on a scenic point to point tour of the Northern Kettle Moraine Ice Age Trail in Greenbush, Wisconsin, on April 11. This supported, noncompetitive run offers 50K and 25K options with aid stations, drop bags, and finish refreshments.

Explore forested ski trails at the Iola Spring Trail Race on April 18 in Iola, WI, with a winding 5k and a rugged singletrack 15k that climbs the ski jumping hill. Free kids 1k runs weather permitting.

Run the scenic Tomorrow River Trail half marathon from Plover to a festive finish at Central Waters Brewing Co in Amherst. Enjoy over nine miles of trail and secure a guaranteed t shirt by registering by May 3.

The Jack Lake Crazy Eights Trail Run will take place in Deerbrook on Saturday 6 June 2026. You can run 10 kilometers.

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.

Take on the Cliff Runner 10K on July 19, 2026 at High Cliff State Park, a rugged singletrack course with rocks, roots and steep climbs. Registration includes a Cliff Runner tee and finisher medal, with proceeds to Purdy Nature Preserve.

Evening trail runs in Nine Mile County Forest this July offer 5K, 10K and half marathon routes on winding single track and ski trails. Headlamps and rustic aid stations set a friendly, adventurous tone for trail fans.

The Ragnar Trail Wisconsin will take place in Wausau from Friday 18 September 2026 to Saturday 19 September 2026. You can run 117 miles.

Run the Twisted Roots marathon or half at High Cliff State Park near Sherwood, Wisconsin. Tackle technical single track, rolling prairie and cliffside views of Lake Winnebago on scenic, community driven courses.

Join a canicross or solo trail run and walk in Denmark, WI on October 17 with 2.8, 5.6 and 8.4 mile routes, raising funds for Crisis Cafe. Celebrate with a costume contest, Paw Parazzi red carpet photos, vendors and food.

Run scenic glaciated woodlands and rolling ridges at the Black River Trail Classic in Millston WI with options from 10k to the 85k ultra. Expect well marked trails, hot finish line food, a winter hat and wooden finisher medals.