Trail Running calendar near Madison 2025-2026

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

The Guv'nor Frozen 50 at Governor Dodge State Park on December 6, 2025 offers 50K, 25K and 15K on scenic winter single track with plenty of climb. Enjoy well stocked aid stations and help support the Driftless Trail project.

Take on the Whitewalker Ultra 100k in Palmyra WI, a two loop 100k over scenic Ice Age Trail and Scuppernong trails. Expect rugged single track, aid stations on course, and a 24 hour finish limit for a true winter challenge.

Take on the Triple D Winter Race in Dubuque County on January 17, 2026 with bike and run distances for every level. Organized by local volunteers, the day ends with warm food and drinks at 7Hills Brewery Event Center and prizes for top fini..

Run or skate across frozen Lake Mendota at the Frozen Assets 5K, starting and finishing at The Edgewater hotel. Enjoy skyline and UW campus views while taking part in a chilly festival favorite, with options for walkers, runners, and skater..

Explore scenic, varied trails at Governor Dodge State Park with the Tour de Dodge, offering 50K, 27K and 10K distances on March 7, 2026. Expect well marked courses, aid stations, and postrace photos and results from the Driftless Trail Coll..

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

Run rolling prairie, single track and sandy hills at the Donald Dash in Donald County Park near Mount Horeb, WI. Choose 5 km or 15 km and support Friends of Donald Park as proceeds fund trail upkeep.

Run the scenic Mines of Spain in Dubuque on May 2, 2026 with 5K 10K and half marathon options. Enjoy clear course support, a custom bib and a rotating race item, plus post race food and a series gift if you register for the full series.

Join the Sugar Badger 50/50 and Half in Belleville, WI for flat, scenic out and back runs on the Badger State and Sugar River State Trails with 50 mile, 50K and half marathon options. Expect trestle bridges, a quarter mile tunnel, aid stati..

Kettle Moraine returns June 13 and 14 2026 in LaGrange Wisconsin, offering 100 mile, 100K and shorter trail distances with plenty of Ice Age Trail scenery. The 100 mile serves as a Western States qualifier, making this a prime summer ultra.

Run the scenic Ice Age Trail at the Whitewater Trail Challenge in Whitewater Wisconsin on June 20, 2026. Pick 50K, half marathon or 10K courses that mix smooth singletrack and technical footing for a rewarding trail day.

Experience Dances with Dirt Devil's Lake, a midsummer trail run on scenic glacial terrain near Baraboo, Wisconsin. Choose distances from 10K to 50 miles and enjoy aid stations, a finisher medal and post race food and a cold brew.

The Echo 136 is a 136 mile trail ultramarathon through the scenic Kettle Moraine and Ice Age State Trail near Whitewater, Wisconsin on September 25, 2026. Expect rugged singletrack, generous aid stations and a 55 hour time limit.

Take in wooded trail views at the Fall Into Fall Trail 5k in Janesville, then stay for live music, food trucks and beer and wine tasting at the festival. Run or walk a fun, scenic course and celebrate the season with community festivities.

Join the Haunted Highlander Assault Trail Run in McHenry on October 3, 2026 for spooky 5 km heats through haunted sets and animatronics. After the run enjoy a costume contest, bonfire, live entertainment and food.

Enjoy a fall run, walk and roll through 125 acres of prairie, ponds and fall color at Zachariah's Acres in Oconomowoc. Choose 5K, half marathon or a family one mile loop while supporting nature based programs for children with special needs..

The Mines of Spain 100 offers 100 mile and 100 kilometer trail ultraruns on scenic loops around Dubuque's Mines of Spain. Expect rugged singletrack, steep climbs and Mississippi River views on a challenging multi loop course.

Join the Jaimie Cox Memorial Run in Roscoe IL on October 17, 2026 for a family friendly 5K or 2 mile walk along the scenic Stone Bridge Trail. Run for a cause as proceeds support the Jaimie Cox Memorial Scholarship.