Trail Running calendar near Deer Park 2026-2027

Trail races at Oakhurst Forest Preserve in Aurora, Illinois, the series includes 5K, 8K, and 10K events in early 2027 with a single registration and series swag rewards; the 8K fee is $65.00.

A winter timed ultra in the Southern Kettle Moraine Forest offering 6, 12 and 24 hour loop options for solo runners and relay teams. The field is limited to 160 participants and the 6 hour option is available in AM and PM waves.

Early-season trail races at The Forge in Lemont, Illinois, on wooded single and double track trails with mud, roots and gravel. Distances offered are 13.1 miles and 6.5 miles with technical singletrack sections.

30k, 50k and 50 mile trail races at Sunset Hill Farm County Park in Valparaiso, IN with one aid station, a 16 hour finish window, and distance-specific finisher awards.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles, IL with a $70 entry fee. The race is part of a winter series that also includes a 5K and 8K and uses a single registration page.

Timed trail event at Lowell Park in Dixon IL featuring multiple distances on an alternating 2.25 mile loop with manual lap tracking and an aid station.

Trailbreaker returns to Waukesha on April 4, 2027 with races from a 1K kids run to a full marathon, plus ruck options and a walk. Proceeds support the Park Foundation of Waukesha and local parks and recreation.

Trail races in Crystal Lake, Illinois on a 5.2 mile loop offering 50k, 15 mile and 5 mile options through single track, prairie and pine forest.

Trail ultraraces at Deer Grove Forest Preserve in Palatine IL featuring 5.5 mile laps, central aid station, inclusion policies and a playful race atmosphere.

Flat out and back half marathon and 10K on the limestone Great Western Trail with a 25 plus year history and proceeds supporting local mental health charities.

Trail marathon and 10 mile on the Sag Valley Trail at Cap Sauers Nature Preserve in Palos Hills, IL, with wide horsetrail, notable elevation gain, and staffed aid stations along the routes.

Looped trail endurance event in Wolf Road Woods offering 7 or 11 hours on a four mile singletrack with an aid station stocked with hot dogs and pixie sticks.

An obstacle course event at Byron Motosports Park on May 22, 2027 offering 10K and 5K waves, Special Forces, Ruck division and a kids course, produced by a nonprofit honoring service members.

Trail races at Waubonsee Community College on June 12, 2027 featuring chip timed 5K and 10K options, packet pickup choices, live results, and awards for the fastest female and male finishers.

Kishwauketoe 5K Run / Walk in Williams Bay featured a main 5K and a kids quarter mile, drew 280 finishers, and proceeded after volunteers cleared storm debris.

A timed long distance walking event at Alpine Valley, Elkhorn, WI on October 9, 2027 offering 7, 14, 21, and 28 mile loops, optional weighted vests, and a 10 hour finish limit.