Trail Running calendar near St. Charles 2026-2027

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.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

A multi-distance trail event in Southern Kettle Moraine State Forest offering ultra distances, a 50K and a 15K Fun Run, with aid stations, pacing rules, finisher awards, and proceeds funding forest projects.

Trail runs and a walking option use a rolling park course that starts at the southwest corner and returns through woods, service road, and open sections with occasional rough footing and visible seasonal foliage.

A trail running event at Camp Big Timber in Elgin with 3 miles, 5 miles and a kids 1/4 mile fun run. The course includes grass, gravel, single-track and a cold creek crossing; proceeds support local youth organizations.

A half trail run at Stoney Run County Park on November 14, 2026 that follows two overlapping loops over grass, gravel, pavement and single-track trails. On-course aid stations are provided and timing uses a popsicle stick system.

Late November trail festival in Lemont IL offering 10K, 20K, 30K and 60K on single and double track and gravel around historic quarries and the I&M Canal. Courses start and finish at The Forge and use lap formats.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

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 four race winter trail series in Dixon, Illinois covering 31 miles from December to March. Races include 5K, 10K, 15K and 20K with series awards and participation merchandise.

A Canicross-focused trail event at Lake Geneva Ziplines and Adventures offering one 4-mile loop or two loops for 8 miles, dog-powered and dog-friendly options, awards for dog teams, on-course drinks but bring a refillable vessel.

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.

A winter timed ultra in Dousman, Wisconsin offering 6, 12, and 24 hour options for solo runners or relay teams of up to four, set in winter woods and on a frozen lake with warming shelters, hot drinks, a meal, and finisher items included.

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 in Valparaiso offer 30k, 50k and 50 mile options with a 16 hour time limit. One aid station is on site and finishers receive event apparel and distance specific awards.

A looped trail event at Lowell Park offering 13.5, 22.5, and 33.75 mile timed races plus a relay, with manual lap tracking, aid station food, entry fees, and awards for top finishers.

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.

Childish Nonsense in Deer Grove Forest Preserve, Palatine IL on April 24, 2027 features looped trail races from 5.5 miles to 50 miles. One aid station at the start/finish is available every 5.5 miles and pacers are allowed for 50 milers aft..

Flat out and back half marathon and 10 km on the limestone Great Western Trail, hosted by Fox River Trail Runners. Registration fees and donations support three local mental health charities.