Trail Running calendar near Chicago 2026-2027

A winter obstacle race at Lake Geneva offering 5K, 10K, a 20K Yeti Challenge, a kids course, team packs and a virtual option. Fun heats allow skipping obstacles while the Elite division requires full obstacle completion for podiums.

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.

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.

A trail race at Sunset Hill Farm County Park offering three distances, a 16 hour finish allowance, a single start/finish aid station, and distinctive finish gifts including belt buckles and a hand-made wooden medal.

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.

A looped ultrarunning event at Deer Grove Forest Preserve west in Palatine, IL offering 50-mile, 50K, 25K and 5.5-mile races on mostly wide, nontechnical trails. The course uses 5.5-mile laps with one aid station at the start and finish.

May 1, 2027 at St. Patrick's County Park near South Bend, Indiana. The event offers 10K, half marathon, marathon and 50K on marked trails with chip timing and packet pickup.

A flat out and back half marathon and 10K on the limestone Great Western Trail, organized by Fox River Trail Runners, with part of registration fees donated to three 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.

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.