Trail Running calendar near Libertyville 2025-2026

The Fancy Nonsense 25K/50K is a whimsical ultramarathon held in the Palos Trail System near Willow Springs and Lemont, Illinois, about 20 minutes from downtown Chicago. Runners can choose from 25K, 50K, or 5-mile distances on a mostly single-track, 5.5-mile loop course that starts and finishes at Re..

Among the Trees is an ultramarathon event held in Dousman, Wisconsin, featuring 100k and 50k race distances. Set within the scenic Southern Kettle Moraine Forest along the historic Ice Age Trail, the course offers runners a challenging and picturesque experience amid vibrant fall colors. Both races..

The Fast Track Cross Country Open is a 3-mile cross country running event held in Schaumburg, Illinois, on the MacNider course near Hoover Elementary School. Open to all ages and abilities, the event features separate women's and men's races. Participants can enjoy running on grass and have the opti..

The Forge Trail Run Festival, held in Lemont, Illinois, offers a challenging late-fall trail running experience with distances of 10K, 20K (half marathon), 30K, and 60K. The courses start and finish at The Forge and wind through single and double-track trails in the woods, gravel paths, and around t..

The Bigfoot Half Trail Run is a half marathon event held at Stoney Run County Park in Hebron, Indiana. Participants complete the race by running two loops around the park's trail. The course features two aid stations: one at the start/finish area and an unmanned station approximately 3.5 miles into..

The Bucks & Does 13.1 Pointer is a trail running event held in Nashotah Park, Wisconsin, featuring distances of 5K, 10K, and a half marathon (13.1 miles). The course is primarily wood-chipped with some grassy sections, shaded by trees for a comfortable run, and is run in a counterclockwise direction..

The Fast Eddie 50k, held at Lapham Peak in Delafield, Wisconsin, is an endurance event featuring a 50K ultra and a 5K race. The 50K consists of five loops on the scenic and challenging Blue Loop trail, known for its rolling terrain and beautiful woodland views. The 5K is an out-and-back course on th..

The Quiet Silence 50k is an ultramarathon held in Lake Mills, Wisconsin, featuring an out-and-back course on the Glacial Drumlin State Trail. Starting at Rotary Park in Lake Mills, runners head west to the trail's terminus in Cottage Grove, covering a mostly flat, crushed gravel path. Participants h..

The Arctic Frog Run in Libertyville, IL, is a challenging endurance event held in early December, featuring distances of 50K, 25K, 15K, 10K, and 5K. The scenic course combines pavement, wooded, and crushed limestone trails around the Des Plaines River and Casey Trails, with rolling hills adding to t..

The Frozen Gnome is a challenging winter trail running event held in Crystal Lake, Illinois, at Veteran Acres park. Featuring a "Triple Black Diamond" rated course, the race offers a 50K ultra run, a 10K race, and relay options for teams of two or five. The course consists of a scenic 10K single-tra..

The Cereal Killer 15k Trail Run takes place at Red Mill County Park in La Porte, Indiana. This trail race features a 15-kilometer course marked with flags and signs, consisting of four loops. Participants are advised to follow course markings carefully rather than other runners.The event offers a fu..

ARKTOS is a challenging ultra running event held in Dousman, Wisconsin, featuring 6, 12, and 20-hour race options for solo runners or relay teams of up to four. Set in a cold, wooded environment with frozen ground, the race tests participants' endurance and mental toughness in potentially uncomforta..

The Tombstone 50 Trail Run is part of the Crazy Legs Race Series held at Sunset Hill Farm County Park in Valparaiso, Indiana. Scheduled for March 14, 2026, the event offers three challenging distances: 30k, 50k, and a newly added 50-mile race. The course features a new layout with more hills, includ..

The Muddy Shamrock @ The Forge is an annual trail running event held in Lemont, Illinois, featuring a Trail Half Marathon (approximately 13.1 miles) and a Trail Quarter Marathon (about 6.6 miles). The race courses wind through wooded single and double-track mountain bike trails and gravel paths arou..

False Spring Trail Runs, held in LaPorte, Indiana, offers challenging trail races on scenic, woodsy single-track paths featuring winding switchbacks and views of lakes and ponds. The event includes a 10K course, which is a single loop of the trails, and a Half Marathon consisting of two laps. The di..

The Earth Day 50k is a trail running event held in Crystal Lake, Illinois, at Veterans Acres Park. It offers three race distances: 50 kilometers, 15 miles, and 5 miles, all starting together on a 5-mile loop course featuring single track trails and rolling hills. The race emphasizes sustainability,..

Childish Nonsense is a trail running event held in Palatine, Illinois, at Deer Grove Forest Preserve West. It offers multiple distances including a 50-mile, 50K, 25K, and 10K, with courses consisting of laps on a mostly wide, non-technical trail. Runners encounter a single aid station at the start/f..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an endurance running event held in the scenic Kettle Moraine State Forest near Dousman, Wisconsin. Participants can choose from multiple race options including 6-hour, 12-hour, and 24-hour solo races, as well as 12-hour and 24-hour relays. The course fe..

The F^3 Cap Sauers Trail Marathon & 10 Mile is a trail running event held at Teason’s Woods in Palos Hills, Illinois. The marathon covers 26.2 miles, featuring two circuits of the 10-mile course plus an additional out-and-back segment, while the 10 Mile race follows the Sag Valley Trail. Both course..