Trail Running calendar near Crown Point 2026-2027

A trail ultramarathon at Red Gate Woods near Chicago offering 25K and 50K on a clockwise single track loop of about 5.5 miles, with staffed aid stations, course maps, and no pacers allowed.

Howloween 5K in Schaumburg is a chip timed 5K run or walk at Busse Woods that supports animal shelters. Pets may join without registration and a virtual participation option is available.

A nighttime run and walk at Lake County Fairgrounds on October 30, 2026 featuring a timed 5K, a non-timed 2K, a market with live performances, costume contests, and awards.

Trail races of about 3 and 5 miles through the woods at Camp Big Timber in Elgin on November 8, 2026. The course runs on grass, gravel and single track and includes a creek crossing, participant shirts and a pancake breakfast.

A 3-mile cross-country race at the MacNider course in Schaumburg on November 8, 2026, with separate women's and men's races, optional team scoring, pre-race packet pickup, and a $25 registration fee.

A half trail run at Stoney Run County Park on November 14, 2026, over two loops of grass, gravel, pavement and single-track trails, with on-course aid stations, on-course flags, packet pick-up at a shelter and raffle items sold for the park..

A trail festival in Lemont on November 14, 2026, offering 10K, 20K, 30K and 60K on single and double-track trails and gravel around the Lemont Quarries and I&M Canal, with multi-lap courses and variable terrain.

The St. Joe Valley Happy Trail Run will take place in Roseland from Saturday 14 November 2026 to Monday 16 November 2026. You can run between 5 and 13 miles.

A trail based Turkey Trot at Southwestern Michigan College offering 10K, 5K and a free 1K kids run, chip timed with live results, guaranteed tech shirts for early registrants and age division medals.

A Thanksgiving 5K on the Green Bay Trail at Winnetka Train Station featuring rolling start waves, a family division, packet pickup before race day, post-race refreshments, and support for local charities.

A 2.5 mile chip timed cross country Turkey Trot on Thanksgiving morning in Orland Park, with long sleeve race shirts, a post race raffle, and prize turkeys for top finishers.

A public cross country race in Evanston with three all-grass loops, team and individual scoring, included long-sleeve race shirt, and a post-race awards cookout; entry fees vary by registration date.

A winter trail series at Dick Young Forest Preserve in Batavia featuring 5K, 8K, and 10K races on separate dates in early 2027, with combined registration and a series swag reward program.

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.

Trail races at Sunset Hill Farm County Park on March 13, 2027 offering 30k, 50k and 50 mile distances; the course includes the Roller Coaster hills, one aid station, and finishers receive medals or belt buckles plus event apparel.

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 lap-based trail event in Palatine, Illinois on April 24, 2027 offering 50 Miler, 50K, 25K and 5.5 Miler races with one aid station at the start/finish and a 7pm cutoff.

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.