Trail Running Calendar Illinois 2026-2027

Join the Miles for Marshall 5K trail run and walk on Saturday, September 26, 2026 at Patriot's Park in Greenville to support childhood cancer research and families. Run or walk scenic trails with community spirit and purpose.

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.

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.

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.

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.

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.

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.

Run the scenic Tunnel Hill Trail from Vienna City Park in a multi distance ultrarunning event from marathon to 100 mile, including the USATF 50 mile championship. This USATF sanctioned UTMB index race is a Western States qualifier with aid..