Trail Running calendar near Yorkville 2026-2027

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

Take on the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K, 10M or relay teams as each loop serves as a 3 to 4 mile Hole. Enjoy golf style scoring for a playful twist on hilly singletrack.

Celebrate the 45th Annual Brickyard Run on June 27, 2026 in Hobart, IN with a family 2K fun run plus timed 5K and 5 mile races along scenic streets and the Oak Savannah Trail. Collect the famous brick awards for top finishers.

Join the CMAR Trail Races at Camp Wokanda July 17 to 19, 2026, offering 100 Mile, 50 Mile, 50K and Half Marathon on scenic, hilly loop and out and back courses. Big elevation and friendly aid stations make it a rewarding trail challenge.

Run scenic single track trails at Twin Creeks Farm in Valparaiso with 4, 9, and 18 mile options across wooded switchbacks, bridges and creek views. All finishers get on site awards and podium prizes await top runners.

Run the Rails in Elburn on August 22, 2026 is a community fundraiser at Prairie Park supporting the Elburn Parks Commission. Choose a 1 mile fun run, a 4 mile or 7 mile race, earn kid medals and age group awards and celebrate local parks.

GristMill Grind is a scenic yet rugged 5K and 10K trail run at Franklin Creek State Natural Area on September 5, 2026. Tackle hilly, technical trails with multiple creek crossings while supporting park conservation.

Experience scenic trails near Naperville at the Naperville Trails Half Marathon and 10K in Wheaton, Illinois on September 5, 2026. In person and virtual entries welcome for runners of every pace.

Experience a flat, fast 104 mile all trail ultramarathon along the historic Hennepin Canal from Sterling to Colona, running past locks, lift bridges and small Illinois towns. Choose 100 mile, 50 mile, 50K or team relay distances, with a nig..

Join Run The Woods on October 3, 2026 at Timber Pointe in Hudson IL for scenic trail races and a fun untimed one mile walk. Proceeds benefit Easterseals Central Illinois and Timber Pointe to help kids attend camp.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

Haunted Highlander Assault Trail Run offers a spooky 5k in McHenry, IL with haunted sets, animatronics and actors across timed heats. Stick around for a costume contest, bonfire, live music and food.

Run from a Half Marathon to 50K and 50 Mile on flat crushed gravel along the Des Plaines River Trail, including a Boston qualifying marathon. Friendly small race with aid stations and finisher medals, so bring your own cup.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

Join Fancy Nonsense for 25k, 50k, or 5 mile trail runs through Palos Trail System near Willow Springs. Mostly runnable single track on a looped course with friendly aid stations and an inclusive vibe from CUSS Running.

Light up the night at Witches in the Woods 5K/2K in Crown Point. Choose a timed 5K run or a fun 2K walk, enjoy costumes, live music, treats and a family friendly market among the fairground trees.

Join the Bigfoot Half Trail Run on November 14, 2026 at Stoney Run County Park in Hebron, IN for a scenic two-loop course across fields, trails and gravel. Enjoy on-course aid, raffle prizes and event merch in a friendly, relaxed race atmos..

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.