Trail Running calendar near Evanston 2025-2026

The Witches in the Woods 5K/2K is a Halloween-themed nighttime running and walking event held at the Lake County Fairgrounds in Crown Point, Indiana. Participants can choose between a timed 5K run or a non-timed 2K walk through wooded trails and roads, so bringing flashlights or headlamps is recomme..

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..

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 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 Fast Eddie 50K and 5K take place at Lapham Peak in Delafield, Wisconsin, celebrating endurance and community while honoring Ed Condon's legacy. The 50K features five loops on the scenic and challenging Blue Loop trail, known for its rolling terrain and beautiful woodland views. The 5K offers an..

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 St. Joe Valley Happy Trail Run takes place at St. Patrick's County Park in South Bend, Indiana.This event offers multiple distances including a 1-mile fun run, 5k, 10k, and a half marathon, all on beginner-friendly trails with beautiful scenery. The course features loops: 5k is one loop, 10k two..

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.

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 quiet, cold forest environment with frozen ground, the race tests participants' endurance and mental toughness in potentially unco..

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 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.