Trail Running calendar near Oakwood 2026-2027

Enjoy a three race series along Plainfield's scenic paved trail system from February to April, featuring bridges, ponds, waterfalls and live chip timing. Complete all three for a custom finisher medal and enjoy awards, hot cocoa and fire pi..

Join the Frozen Cock's Crow 5K at Willenborg Woods, a spirited trail run on technical singletrack with steep climbs and a stream crossing. Enjoy a family friendly, grassroots vibe and a fun post race celebration.

Run the festive Fat Tuesday 5K or 10K at Keg Grove in Bloomington along the Constitution Trail. Grab Mardi Gras beads, enter a King Cake raffle and enjoy post race drinks while supporting St Vincent De Paul.

Join the Plainfield Race Series from Feb 7 to Apr 11, 2026 for 5k, 10k and 10 mile races on scenic paved trails with bridges, ponds and parks. Enjoy chip timing, custom shirts and a series finisher medal plus post race hot cocoa and fire pi..

Run scenic singletrack and rolling hills at Owen Putnam State Forest on March 21, 2026, with distances from 10K to 50 miles. This cupless event requires you to carry hydration and includes swag, medals and age awards.

Run scenic single track loops around Clinton Lake with 30 mile and 10 mile options on March 28, 2026. Expect rolling terrain, fully stocked aid stations, finisher swag and a community focused event supporting local trail maintenance.

Allerton Races on April 11 and 12, 2026 features trail and road routes, a glowing nighttime Trail Glo 5K and virtual options for every pace. Proceeds support Robert Allerton Park and Make A Wish Illinois with Wish Warrior recognition.

Join the Plainfield Race Series from Feb 7 to Apr 11, 2026 for 5k, 10k and 10 mile races on scenic paved trails with bridges, ponds and parks. Enjoy chip timing, custom shirts and a series finisher medal plus post race hot cocoa and fire pi..

Join the 28th annual Lake Mingo Trail Run on June 13, 2026 at Kennekuk Cove County Park, a scenic 7.1 mile loop mostly on natural trails with rolling hills and nine bridges. Celebrate afterward with food, beer, and great trail camaraderie.

Join the Madder Than A Wet Hen 5K in Charleston IL for a rugged forest trail run featuring a knee deep river crossing and a fierce climb up Billy Goat Hill. Reward yourself after the finish with pancakes and ice cream.

Run a scenic 10k around Stryker Lake at Griffin Bike Park with rolling hills, wide trails and two friendly laps that make passing easy. Camping at Fowler Park and the concurrent DINO Gravel Triathlon create a lively event atmosphere.

Hit the Wild Wild Wilderness at Kickapoo State Recreation Area on September 12, 2026 with 5K or a rugged 7.45 mile trail through woods, steep climbs and creek crossings. Celebrate finishes with food, drinks and awards.

Run fast rolling trails at Sand Creek in Decatur on Sept 12 and choose 4.4 or 7.6 miles for a lively trail challenge. Get a tech shirt and finisher medal while supporting the Special Operations Warrior Foundation.

Hit the trails at Run The Woods on October 3, 2026 in Hudson IL with 5K and 8K races, youth divisions, and a one mile trail walk for all ages. Proceeds support Easterseals Central Illinois and Timber Pointe Outdoor Center.

Shake Your Trail Feather is a two day trail race at Willenborg Woods that winds single track trails, creek crossings and rolling climbs. Distances from 5K to 100K, full course support and a lively post race celebration.

Enjoy a scenic and challenging 5.7 mile trail run along the Sangamon River at Robert Allerton Park in Monticello IL, finishing in a meadow. Proceeds support park trail care and there is a 2 mile nature walk plus a virtual option.