Trail Running calendar near Orland Park 2025-2026

Run or walk the Howl o'ween 5k at Busse Woods for a festive Halloween celebration that supports animal charities. Costumes and dogs are welcome on the flat paved course, with shirts, medals and finish treats for humans and pups.

Join the Fancy Nonsense 25k or 50k for a whimsical trail ultra through Palos Trail System near Chicago, featuring runnable single track loops and full aid stations. Expect mischief, laughs, and a joyful return to the love of running.

Join the ERC John Hennelly Public Cross Country Races at Lovelace Park in Evanston on October 26 2025. Community, open and masters races run a three lap 3.5 mile course across hills and fields. Teams and all ages welcome rain or shine.

The Grand Mere Challenge 5K is a 5K trail race in Stevensville, Michigan, starting and finishing inside Grand Mere State Park. The course blends rolling sand dunes, shaded forest singletrack, and scenic stretches along Lake Michigan, delive..

Join the Bristol Woods Trail Run at Pringle Nature Center for a scenic 5K and a 2 mile hike through beautiful wooded trails. Held the first Saturday in November, proceeds support environmental education at Pringle Nature Center.

Turkey Trails - Greater Chicago is a Thanksgiving-themed running event in Shorewood, Illinois, held at Hammel Woods Route 59 Access (554 Brook Forest Ave). It offers in-person distances of 1 mile, 5k, 10k, a Kid’s Dash, plus a Virtual Race..

Event details The Big Timber XC Challenge takes place Sunday, November 9, 2025 at Camp Big Timber, Big Timber Road at Tyrrell Road, Elgin, Illinois. Distances offered: 3 miles - one loop of the perimeter trail 5 miles - two loops of the pe..

Run the Fast Track Cross Country Open in Schaumburg on Sunday November 9 with separate men and women races on a scenic 3.05 mile looped grass course. Open to all ages and abilities, teams are welcome.

Take on two scenic loops at Stoney Run County Park for the Bigfoot Half Trail Run on November 15, with proceeds supporting the park. All finishers get a Bigfoot trucker hat, gloves and a handmade wooden medal plus a raffle chance.

The Forge Trail Run Festival takes place at The Forge: Lemont Quarries in Lemont, Illinois, a late‑fall Midwest trail event set among woods, gravel paths, and the historic Lemont Quarries and I&M Canal. Runners may choose from 10K, 20K (Hal..

Join the Abominable Trail Race at LG Ziplines near Lake Geneva on November 15, 2025 for scenic 5K, 15K and 30K trail courses with individual and relay team options. Finishers get a medal, tee and a craft beer or hot cider.

Join the Orland Park Turkey Trot on Thanksgiving morning for a chip timed 2.5 mile run through scenic roads, paths and woods near Village Hall. Finishers get a long sleeve dri fit shirt, raffle entry and a chance to win a prize turkey.

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Chicago Gaelic Park Carraig Challenge The event is a cross country running and walking event at Chicago Gaelic Park / Carraig Irish Pub in Oak Forest, Illinois, on Sunday, November 30, 2025. Two course options are offered: 5K run 1.5 mile..

Kick off the year with the Frozen Feet 5k Trail Run at Creek Ridge Park, a two loop winter trail with a couple of hills and natural footing. Finishers get a winter hat and gloves plus snacks and medals.

Conquer winter trails at the Frozen Gnome in Crystal Lake on January 10, 2026, a technical single track 10K loop repeated for the 50K or tackled in relays. Expect triple black diamond terrain, a Gnome Depot aid station, and a finisher medal..

Event overview The 50K MASHUP SLAM is a series of trail races in the Midwest based on the 50K distance. The series includes multiple events across the year, begins with the Frozen Gnome 50K in January and concludes in November with the Mine..

Tackle winter trails in the Fox Valley with a three part Challenge Series featuring a 5K in Batavia, 8K in Aurora and 10K in St Charles across Jan to Mar. Register single or as a bundle and earn upgraded swag for multiple races.

Run the Cereal Killer 15k at Red Mill County Park for a friendly four loop trail challenge hosted by the Crazy Legs Race Series. Finishers get swag and a cozy post race cereal buffet with milk options and coffee.

The Yeti Trail Half Marathon will take place in Westville on Saturday 21 February 2026.