Trail Running calendar near Rolling Meadows 2025-2026

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second loop to the Scuppernong Trails and back, totaling 100 kilom..

Cereal Killer 15k Trail Run takes place at Red Mill County Park, La Porte, Indiana. This Crazy Legs Race Series event offers a 15-kilometer trail, run as four loops on a marked course through park terrain. The atmosphere is low-key and fun, with old-school timing: finishers receive a numbered popsic..

ARKTOS is a winter ultramarathon held in Dousman, Wisconsin, within the Southern Kettle Moraine Forest, and part of the Golden Kettle Trail Series. It offers 6-, 12-, and 20-hour options for solo runners or relay teams up to four. Runners complete as many loops as possible on a snow-covered forest c..

Set in Sunset Hill Farm County Park in Valparaiso, Indiana, Tombstone 30k/50k/50 mile is a Crazy Legs Race Series trail event offering three distances: 30k, 50k, and 50 miles, with a new 2026 course. The mostly non-pavement course features the famed Roller Coaster hills and includes an aid station a..

Muddy Shamrock @ The Forge is a trail running event held at The Forge: Lemont Quarries in Lemont, Illinois. The race offers two distances: Trail Half Marathon (about 13.1 miles, run as two laps) and Trail Quarter Marathon (about 6.6 miles, one lap) on wooded single- and double-track trails around th..

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 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..

Set in Palos Hills, Illinois, the F^3 Cap Sauers Trail Marathon & 10 Mile runs through the Cap Sauers Holding Nature Preserve, the largest tract of undeveloped land in Cook County. The event offers two distances: a marathon (26.2 miles) and a 10-mile option. The course uses the Sag Valley Trail syst..

Chicago Yeti 7-11 Hour Endurance Run is held at 9800 Wolf Rd, Willow Springs, IL. The race centers on a four-mile loop through Palos Preserves, featuring a mix of single-track forest, double-track trails, rolling hills, and quick runnable sections that suit a range of paces. The atmosphere blends sk..

JH Memorial 5 Mile Trail Run takes place at Stoney Run County Park, Hebron, Indiana. The Crazy Legs Race Series offers a 5-mile trail course through park trails in a low-key atmosphere. The course is marked with flags and arrows at major turns; an aid station with water and Gatorade appears around m..

Kettle Moraine is a renowned ultra marathon held in LaGrange, Wisconsin, featuring multiple race distances including a 100-mile, 100K, 50K, 38-mile, and a 100-mile relay. Established in 1996, it is one of the oldest 100-mile races in the U.S. The course is 100% trail, with about 65 miles on the scen..