Trail Running calendar near Libertyville 2026-2027

Trail races on a 5-mile loop at Veterans Acres in Crystal Lake, IL, offering 50K, 15-mile, and 5-mile options with a single major aid station, age-group awards, an 8-hour cutoff, and packet pickup the day before and race day.

Run through the scenic rolling trails of the Morton Arboretum on a USATF certified 10K course. Enjoy a lively post race party with live music and refreshments while supporting vital tree conservation and research.

A looped trail event at Deer Grove Forest Preserve in Palatine, IL offering 10K, 25K, 50K and 50 mile distances on mostly wide, non-technical trails with a single aid station at the start and finish.

Experience a bib timed run through the natural twists and turns of Saw Wee Kee Park. Join this spring event to earn a unique medal piece and enjoy the changing seasonal terrain in Yorkville.

Experience a flexible trail series in the Kettle Moraine Forest featuring seven races with open start times, live music, and handcrafted finisher medals.

Run or walk to support Anderson Humane at their largest fundraiser. Choose a timed 5K run or bring your dog for a 1.5-mile walk along the Batavia Riverwalk. The event includes awards, a lure course, and activities for animal lovers.

The Prickly Pine Jackpot 24 Hour offers timed running events in the scenic Kettle Moraine State Forest. Runners choose from three different loop distances to build their mileage, with cash jackpots for top solo and relay finishers. Amenitie..

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.

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.

Experience a scenic trail run through the Sag Valley Trail system with a marathon or 10 mile distance. Enjoy a non technical horse trail course followed by post race chili and beer at Teason’s Woods.

A classic Midwest ultra on varied glacial terrain offering 50-mile, 50K and half-marathon options with scheduled training runs, a strict no-transfer policy and on-site medical support.

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.

A low-impact trail event at Lapham Peak Park offering distances from a Kiddos 1K to a half marathon, with ruck and walk options, cupless aid stations, and proceeds benefiting Tall Pines Conservancy.

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.

Frontline OCR at Byron Motosports Park on May 23, 2026 offers 10K and 5K obstacle courses, a ruck division, a kids mile, Special Forces and Heroes waves, plus team entry packs, organized by a 501(c)(3) foundation.

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.