Trail Running calendar near Wheaton 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 encourages joy and imagin..

The Fast Track Cross Country will take place in Schaumburg on Sunday 9 November 2025. You can run 3 miles.

The Big Timber XC Challenge will take place in Elgin on Sunday 9 November 2025. You can run between 3 and 5 miles.

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 will take place in Hebron on Saturday 15 November 2025. You can run 13 miles.

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or teams of 2 to 4 in relay format. Participants navigate chall..

The Arctic Frog Run in Libertyville, IL, is a challenging winter endurance event featuring multiple race distances: 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 the ch..

The Frozen Feet 5k Trail Run will take place in Michigan City on Saturday 3 January 2026. You can run 5 kilometers.

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 and a 10K race, both run on a scenic 10K single-track loop through Veteran Acres and Sterne’s Woods. Th..

The Whitewalker Ultra 100k is a challenging winter ultramarathon held in Palmyra, Wisconsin, starting at the Emma Carlin Trailhead. Participants complete two 50k loops within 24 hours, traversing the Ice Age Trail to Whitewater and returning, then heading to the Scuppernong Trails and back. The race..

The Cereal Killer Trail Run will take place in La Porte on Saturday 7 February 2026. You can run 15 kilometers.

The Tombstone 50 Trail Run will take place in Valparaiso on Saturday 14 March 2026. You can run between 30 and 50 miles.

The Muddy Shamrock @ The Forge is a 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 takes place on wooded single and double-track mountain bike trails, as well as gravel paths around the..

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 te..

The Skunk Ape 806/314 Trail Race, held at Lowell Park in Dixon, Illinois, offers challenging trail running events on March 21, 2026. Participants can choose between a 33.75-mile race to be completed in 8 hours and 6 minutes, a 13.5-mile race with a 3 hour and 14 minute limit, or a relay option. The..

The Save the Drama for Your Llama 6 Hour Trail Run will take place in La Porte on Saturday 4 April 2026. You can run 6 kilometers.

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 environmental re..

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

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 features a challenging course on the Sag Valley Trail, consisting of wide horse trails with minimal technical terrain but significant elevation—1050 ft for the marathon..

The JH Memorial 5 Mile Trail Run will take place in Hebron on Monday 25 May 2026. You can run 5 miles.