Trail Running calendar near Chicago 2026-2027

Experience an illuminated night obstacle race in Mchenry featuring torch lit trails and technical rigs. Participants can enjoy live entertainment and bonfires after completing their 5k or unlimited lap challenge.

Join this trail event at Potato Creek State Park offering a 10k loop course for multiple distances including a 50k and marathon. Enjoy chip timed races and clearly marked trails in a relaxed park setting.

Experience the Three Ravines Course at Wolf Road Woods with distance options of 3.1 or 5.4 miles. This family friendly trail event features a mix of single track terrain and a post race celebration with craft brews.

Test your discipline in this 6 hour trail challenge where you must complete a 5K every hour to stay in the race. Earn unique patches and medals while navigating the natural terrain of Deer Grove East.

Run a flat, out-and-back course on the historic Great Western Trail. Choose from a half-marathon or 10K distance. Your registration supports local mental health charities.

Trail marathon and 10 mile on the Sag Valley Trail at Teason's Woods featuring substantial elevation, multiple aid stations, sunflower shirts and wooden finisher sunflowers, plus post race chili, beer and awards.

A timed endurance trail event near Willow Springs on a 4 mile loop with single and double track, rolling hills, a signature aid station offering snacks and drinks, and a mandatory reusable cup policy.

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

Navigate the single track routes and wooded hills of the Outback Trail at Imagination Glen. This event features a 12K race and a 3K kids run through shaded terrain with mud and water crossings.

A chip timed 10K through mostly crushed limestone trails and wooded scenery at The Forge Lemont Quarries near Lemont, IL. Part of the Chicago Racing Circuit with overall and age group awards and a 450 runner capacity.

A five-mile trail run at Stoney Run County Park on May 25, 2026, with marked trails, an aid station near mile three, possible mud and a pond crossing, manual timing, and post-race refreshments.

Join the free Dirt Circus community running festival in Crystal Lake on May 30, 2026. Choose between a 4.3-mile or 6.8-mile social group run, then enjoy a festival with food, an expo of local brands, and a raffle. Meet race directors and co..

Backyard Nonsense is a timed trail event with 24, 12, 6, and 3 hour options in the Richard Bong State Recreation Area. Run as far as you want on rolling hills near Vern Wolf Lake. The event is organized by CUSS Running, which has specific p..

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

This 5K run/walk takes place on the Rock Run Greenway Trail in Joliet, starting and ending at Cemeno's Pizza. All proceeds support local cancer patients through the Pat Clark Cancer Foundation. Registration includes a T-shirt and finisher m..

Trail race at Hickory Knolls Nature Area in St Charles with 5K, 10K, and a 2 person 10K relay on June 7 2026. The course runs on dirt, grass and gravel paths with marked loops and limited on course water.

Experience an authentic cross country race on a purpose built grass course in Geneva Illinois. Run as an individual or part of a team on this wide professional grade venue featuring rolling terrain and a classic atmosphere.

A 7 km lollipop loop at Potato Creek State Park with wide, stable paths and two notable hills. The race is part of the DINO Trail Run Series and awards bonus points plus medals for overall and age group placings.

A one day trail stage race using golf style scoring where runners start each hourly hole together and aim for the lowest cumulative stroke total. Options include a 50K (nine holes) and a 10 mile course (three holes) in Valparaiso, IN.

Celebrating its 45th year, the YMCA Brickyard Run features a 5 Mile Gold Cup race, a 5K for younger runners, and a new 2K Family Fun Run/Walk. The event is known for its unique brick awards and supports a local YMCA scholarship fund.