Trail Running calendar near Iola 2026-2027

We have found 14 Trailruns within 80 miles of Iola. See below where and when you can find the races.

Celebrate the season with a 5K run through the scenic trails of Brown County Reforestation Camp. Finishers get a bottle of local maple syrup, and a pancake breakfast is included. The event also features a family-friendly fun run and support..

April 2026

A point to point trail run on the Northern Kettle Moraine Ice Age Trail near Greenbush, WI. Offers 25K and 50K distances with transportation to starts, aid stations, and a finish area with food and shelter.

A spring trail event at the Iola Winter Sports Club offering **5k** and **15k** courses on ski trails and singletrack, plus a free kids 1k when weather permits. Food and drinks will be available in the Chalet and entry fees change after Mar..

May 2026

A half-marathon on May 31, 2026, starting in Plover, WI and finishing in Amherst at Central Waters Brewing Co., with over nine miles on the Tomorrow River Trail. T-shirt size guaranteed for registrations completed by May 3.

June 2026

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

July 2026

Event Overview The DWD Devil's Lake is a trail running event scheduled for July 11, 2026. It takes place at Devil's Lake, an area noted for its geological features formed in the ice age. The event is located in Baraboo, Wisconsin, just nort..

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.

An evening trail race at Nine Mile County Forest using a 5K lap format to offer 5K, 10K, and 20K options on single-track and ski trails; lights are required since the run begins at sunset. Kids events take place the following day.

August 2026

Underdown Trail Races The Underdown Trail Races are grassroots trail runs and mountain bike races held on August 15, 2026, at the Underdown Trail system in Merrill, Wisconsin. The running events include a 60k, marathon, and half marathon. T..

September 2026

Ragnar Trail Wisconsin is a two-day team relay on September 18-19, 2026, at Nine Mile Forest near Wausau. Teams of 2 to 8 runners tackle 117 miles of forested single-track trails. The event features a central campsite village with bonfires,..

Trail races at High Cliff State Park featuring full and half marathon distances on single track, prairie and cliffside terrain with a cupless event policy and postrace pasta buffet.

October 2026

A multi-distance trail event at Mirror Lake State Park on October 3, 2026, with a kids mile, 5K, 10K and half marathon; chip-timed races, cupless aid, park trail terrain and post-race s'mores while raising funds for park projects.

Join the charity trail run or walk in Denmark, Wisconsin. Choose your distance for canicross with your dog or go solo on the wooded trails. The event includes a costume contest and supports the Crisis Cafe.

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.