Trail Running calendar near Lake Geneva 2026-2027

Hickory Knolls Trail Run The event is the sixth annual Hickory Knolls Trail Run & Relay. It takes place at the Hickory Knolls Nature Area within James O. Breen Community Park in St. Charles, Illinois. The event is the second installment..

The Kettle Moraine will take place in Whitewater from Saturday 13 June 2026 to Sunday 14 June 2026. You can run between 50 and 100 miles.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

A cross-country event in Williams Bay featuring a 5K run/walk and a children's quarter mile walk/run. The course follows grass trails through hills, woods and prairie, with parking and restrooms provided.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

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..

The Gristmill Grind 10K will take place in Franklin Grove on Saturday 5 September 2026. You can run between 5 and 10 kilometers.

The Naperville Trails Half Marathon & 10K is set for September 5, 2026 in Wheaton, Illinois. Runners can choose from half marathon and 10K distances, with virtual options also available.

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..

The Bloomingdale Trail 5K will take place in Chicago on Saturday 26 September 2026. You can run 5 kilometers.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

A fall event at Zachariah's Acres in Oconomowoc that raises funds for children with special needs. Routes include a half marathon, two 5K options including ruck, and a one mile family walk and roll through prairie and woodland scenery.

The Des Plaines River Trail Races will take place in Lake County on Saturday 10 October 2026. You can run between 21 and 80 kilometers.

Run or walk on scenic trails at Fox Hill Nature Preserve to support land conservation. Choose from a 5K, 10K, or a 1-mile trail walk through forests and prairie. The event is chip-timed and benefits the Cedar Lakes Conservation Foundation.

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..