Trail Running calendar near Orland Park 2025-2026

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.

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 Bigfoot Half Trail Run at Stoney Run County Park for a scenic two loop half marathon that benefits the park. Runners get a Bigfoot trucker hat and gloves and finishers earn a homemade wooden medal plus a raffle ticket.

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.

Take on the 50K MASHUP SLAM, a Midwest trail series that spans eight scenic events and rewards runners who finish five races with a special finisher buckle. Top series placers earn awards at the final G.O.A.T.z or Miner 49'er event.

Challenge winter single track trails at Veteran Acres and Sterne's Woods in Crystal Lake on a triple black diamond course offering 50K, 10K and relays. The 50K is five laps of a 10K loop with a warm Gnome Depot serving hot food and coffee.

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.

Lace up for the Foot Pursuit 5K at Sunset Hill County Park in Valparaiso on March 7 and tackle a scenic, wooded course with rolling hills. Finishers enjoy awards, plenty of postrace food, and a welcoming community vibe.

Muddy Shamrock at The Forge in Lemont is a scenic but technical trail race with half and quarter options over wooded single and double track, rocks, roots and mud. Chip timing, a race shirt, age group awards and a festive post race party aw..