Trail Running calendar near Portage 2026-2027

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.

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.

Camp Tecumseh’s tenth annual Running with Raccoons 5K takes place April 26, 2026 in Brookston, Indiana. This chip timed run/walk raises funds for the campership fund and follows a scenic route through camp grounds.

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.

A trail marathon and a 10 mile race at Teason's Woods on May 9, 2026, run on the Sag Valley Trail. Wide horse trails, notable elevation, multiple aid stations, sunflower-themed shirts and wooden finisher sunflowers.

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.

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..

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.