Trail Running calendar near St. Charles 2026-2027

Childish Nonsense is an April trail race at Deer Grove Forest Preserve with looped distances from 10K to 50 mile. Expect playful shenanigans, regular aid at the start area, and free entries for BIPOC and LGBTQ+ runners.

Run the Great Western Half Marathon and 10K on a flat out and back limestone path along the historic Great Western Trail. Hosted by Fox River Trail Runners, this longtime race supports local mental health charities.

Take on scenic trails through Teason's Woods at Cap Sauers Holding Nature Preserve with marathon and 10 mile options on wide horse paths. Enjoy rolling hills, well stocked aid stations, limited parking and a unique wooden finisher medal.

Experience the Jennie Hamilton Memorial 5 mile trail run at Stoney Run County Park in Hebron, Indiana on May 25, 2026. Expect scenic but rugged trails with a pond crossing option, midcourse aid, and a finisher water bottle.

Free one day running festival in Crystal Lake celebrating local races, clubs, and brands. Pick a 4.3 or 6.8 mile social run, browse the expo, enter raffles, demo gear, and enjoy food, drinks and community fun.

Celebrate the 25th anniversary 5K for Double "J" in Joliet on June 6, 2026 as participants run the Rock Run Greenway and finish at Cemeno's. Proceeds support the Pat Clark Cancer Foundation and registration includes a T shirt and medal.

Kettle Moraine Ultramarathon in La Grange WI on June 13 and 14, 2026 showcases rugged, scenic trails with about 65 miles on the Ice Age Trail. Distances from 38 to 100 mile plus 100K and a 4 person relay; 100 mile offers a Western States qu..

Hit scenic Ice Age Trail terrain in Whitewater Wisconsin with 10K, Half Marathon and 50K options across rolling, sometimes technical trails. Pick a distance for a relaxed summer challenge or a rugged ultra with great views.

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

Take on the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K, 10M or relay teams as each loop serves as a 3 to 4 mile Hole. Enjoy golf style scoring for a playful twist on hilly singletrack.

Celebrate the 45th Annual Brickyard Run on June 27, 2026 in Hobart, IN with a family 2K fun run plus timed 5K and 5 mile races along scenic streets and the Oak Savannah Trail. Collect the famous brick awards for top finishers.

Run scenic single track trails at Twin Creeks Farm in Valparaiso with 4, 9, and 18 mile options across wooded switchbacks, bridges and creek views. All finishers get on site awards and podium prizes await top runners.

Run the Rails in Elburn on August 22, 2026 is a community fundraiser at Prairie Park supporting the Elburn Parks Commission. Choose a 1 mile fun run, a 4 mile or 7 mile race, earn kid medals and age group awards and celebrate local parks.

GristMill Grind is a scenic yet rugged 5K and 10K trail run at Franklin Creek State Natural Area on September 5, 2026. Tackle hilly, technical trails with multiple creek crossings while supporting park conservation.

Experience scenic trails near Naperville at the Naperville Trails Half Marathon and 10K in Wheaton, Illinois on September 5, 2026. In person and virtual entries welcome for runners of every pace.

Echo 136 is a 136 mile trail ultra through the scenic Southern Unit of Kettle Moraine State Forest near Whitewater, Wisconsin, following the Ice Age State Trail. Runners have 55 hours to tackle varied terrain with stocked aid stations along..

Experience scenic 4 mile loops across grassy fields and single track trails at Tryon Farm, with distances from a 2 mile fun run to a 50k ultra. Proceeds support Tryon Farm Institute and the race is part of the Crazy Legs series.

Experience a flat, fast 104 mile all trail ultramarathon along the historic Hennepin Canal from Sterling to Colona, running past locks, lift bridges and small Illinois towns. Choose 100 mile, 50 mile, 50K or team relay distances, with a nig..

Join the Fall into Fall Trail 5k in Janesville on October 3 for a scenic run or walk along tree lined dirt trails. Stick around for the Fall Into Fall Heritage celebration with live music, food trucks and tastings.

Haunted Highlander Assault Trail Run offers a spooky 5k in McHenry, IL with haunted sets, animatronics and actors across timed heats. Stick around for a costume contest, bonfire, live music and food.