Trail Running calendar near Freeport 2026-2027

Challenge yourself on the scenic trails of Iowa's Mines of Spain with 4-mile, 7-mile, and half marathon races. The courses feature a mix of prairie paths, forest tracks, and blufftop views. Proceeds support local trail conservation.

This annual community event in Sun Prairie features a 5k race and a kids' fun run, with a course on neighborhood bike paths. Proceeds go directly to support the local high school cross country team.

Run the Hawk offers timed trail challenges on a scenic 2.25-mile loop at Wisconsin's Blackhawk Ski Club. Choose from 3, 6, or 12-hour solo or relay events, or a shorter 1.7-mile fun run. The event features unique course landmarks, team tent..

Run the Rails offers a unique 1, 4, or 7-mile run starting from Prairie Park in Elburn. The courses cross a rail line bridge, providing views of the surrounding countryside. This community event supports the Elburn Parks Commission.

The Summer Trail Classic offers three distances on the single-track trails of Paul Douglas Forest Preserve. It's the third race in a yearly trail series, with proceeds supporting local trail maintenance. Participants receive a running vest..

Explore the diverse trails of Scott County Park at the ScoCo50 trail run. Choose from 50K, 10 mile, or 5 mile distances on a forgiving course through woods and prairie. The event includes aid stations and supports the local park.

Experience a technical trail race through the bluffs and forests of Franklin Creek State Natural Area. Choose between 5K and 10K distances featuring multiple creek crossings and significant elevation gains.

Course and Terrain The Echo 136 is a 136-mile ultramarathon that uses the Ice Age State Trail. The course travels north from the Southern Unit of the Kettle Moraine State Forest near Whitewater, Wisconsin. The terrain includes wide groomed..

Event Details The Hindsight Ultra Trail Runs take place in Dixon, Illinois. The event offers four distances: a 100 Miler, a 100k, a 50k, and a 25K. The course consists of loops starting behind the Dixon Park District Facility. Each loop is..

Trail races through the Swiss Valley Nature Preserve feature 5.2-mile, 25K, and 50K distances on a rugged loop with creek crossings. The event includes free camping, showers, and shuttles, with proceeds supporting local conservation.

A point to point, all trail ultramarathon along the Hennepin Canal State Trail in northwest Illinois. Multiple distances from 50K to 100 miles, with aid stations every 3 to 7 miles and a 30 hour cutoff for Western States qualification.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

The Autumn Leaf Run will take place in Freeport on Saturday 3 October 2026. You can run 5 kilometers.

Event Overview The Broken Rock Trail Runs take place at Bethel Horizons in Dodgeville, Wisconsin, within the Driftless Area. The event name comes from the Broken Rock Trail, which features a steep rock-stair climb near the finish. Distances..

Event Overview The Mines of Spain 100 is a trail race taking place in Dubuque, Iowa. The event offers two distances: a 100-mile race and a 100-kilometer race. Both races start at Louis Murphy Park. Course Details The course consists of a lo..

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Take on the Soul Crusher trail run through the forested paths of Veteran Acres & Sternes Woods in Crystal Lake. The event features a 5-mile loop course with a chance for extra mileage, finishing with a unique skeleton medal. Prepare for a c..

Experience a seasonal 5k trail run in Pingree Grove featuring haunted sets and live actors. Enjoy a post race bonfire, costume contest, and live entertainment after your run.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

The Abominable Trail Race offers trail distances from 5K to 30K at LG Ziplines and Adventures. Run solo or form a relay team for the 30K. The event includes a festival base camp with music, food, and vendors.