Trail Running calendar near Oakwood 2025-2026

Hit the trails at Timber Pointe for a scenic cross country style 8K, 4K or multi lap challenge with possible deer and eagle sightings. Partial proceeds benefit the nature center and finishers enjoy post race food and warm company.

Start 2026 at the Siberian Express, a 7.45 mile winter trail run at Kickapoo State Recreation Area on January 3. Expect steep climbs and creek crossings, carry your own hydration, and warm up at a friendly post race gathering.

Run the Frozen Cock's Crow 5K in Willenborg Woods on Feb 14, 2026, a rugged winter trail with steep climbs, a stream crossing and scenic singletrack. Join the trail community afterward for food, fun and warmth.

OPSF5050 in Owen Putnam State Forest near Poland IN offers 50 mile, 50K, 14 mile and 10K trail races. Enjoy mostly singletrack, rolling hills and technical terrain on a scenic lollipop loop and remember this cupless event requires carrying..

Run scenic trails and roads at the Allerton Races in Monticello on April 11 and 12 with in person and virtual half marathon, 10K and 5K options. Proceeds benefit Robert Allerton Park and Make A Wish Illinois.

Join the 28th annual Lake Mingo Trail Run on June 6, 2026 in Danville, IL for a scenic 7.1 mile loop of trails, hills and marshes where mud and wildlife add to the fun. Celebrate with food and beer at the post race party.

Take on Madder Than A Wet Hen, a rugged 5K trail race at Willenborg Woods in Charleston on July 25, 2026, with river crossings, steep climbs and roughly 1,100 feet of gain. Field limited to 125, with post race pancakes and ice cream.

Run the rugged Wild Wild Wilderness at Kickapoo State Recreation Area with a scenic 7.45 mile trail or 5K option. Expect steep climbs, creek crossings, awards at the finish and the chance to complete the Grand Slam.

Hit the fast rolling Sand Creek trails near Decatur with 4.4 or 7.6 mile options, in person or virtual. Enjoy a technical long sleeve shirt, finisher medal and snacks while supporting the Special Operations Warrior Foundation.

Run The Woods in Hudson IL offers scenic trail 5K and 8K races plus untimed family walks, welcoming youth and adult participants. Proceeds benefit Easterseals Central Illinois and Timber Pointe to help kids of all abilities attend camp.

Shake Your Trail Feather runs October 16 and 17, 2026 at Willenborg Woods in Charleston, IL, with distances from 100K to 5K on winding single track, creek crossings and riverside paths. Friendly trail support and a post race celebration awa..

Run or walk through Robert Allerton Park on October 25, 2026 with a scenic and challenging 5.7 mile trail run, a relaxed 2 mile nature walk, or a virtual option. A portion of proceeds helps maintain trails and park amenities.