Trail Running calendar near Kankakee 2025-2026

Join DBC Gifts of Love Community 5K in Flossmoor on June 20, 2026, for a scenic 5K at Vollmer Road Grove Forest Preserve or run the Virtual 5K. Help send backpacks, school supplies and gift cards to local homeless students.

Take on the Trail Golf Endurance Challenge in Valparaiso on June 27, 2026 at Trailyard Outpost. Choose 50K, 10 mile or relay teams and tackle looped timed holes with rolling climbs and golf style scoring that blends pace and strategy.

Tackle tree covered single track and creek crossings at Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 18 mile, 9 mile, and 4 mile options for all abilities. Custom finisher awards and youth pricing make this a fun family friendl..

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 scenic loops through Tryon Farm's grassy fields and single track trails while supporting the Tryon Farm Institute. Choose distances from a 2 mile fun run up to a challenging 50k in this inclusive Crazy Legs Race Series event.

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.

Fancy Nonsense is a looped trail race at Red Gate Woods near Willow Springs and Lemont, Illinois, with 50K, 25K and 5 mile options on runnable singletrack. Expect repeated 5.5 mile loops, plentiful aid and classic ultra snacks.

The Forge Trail Run Festival in Lemont Illinois offers 10K to 60K on scenic single and double track trails around the quarries and the I&M Canal. Field capped at 400 with lap courses that call for trail shoes and self supported hydration.