Trail Running calendar near Roscoe 2026-2027

A seven month trail series around Oconomowoc offering 5K, 10K, half marathon and ruck options, an All Access pass to skip packet pickup, a championship finale, and free Kiddo 1K races.

Experience a 4 mile trail run through the historic St James Farm in Warrenville. Enjoy a scenic single loop course featuring rolling terrain, limestone paths, and wooded trails with awards for multiple age categories.

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.

A trail race at Donald County Park in Mount Horeb on May 2, 2026, offering 5 km, 15 km and a Kids One Mile Fun Run; chip timing, aid stations, awards, and proceeds benefit Friends of Donald Park for trail maintenance.

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.

Rumble on the Ridge is a Last Person Standing loop race in Arena, Wisconsin on May 16, 2026 where runners repeat a roughly one mile loop with a twenty minute cutoff until one person completes every lap.

Timed 8 hour and 4 hour loop trail events at Chestnut Mountain Resort near Galena, Illinois, with 2.91 and 0.6 mile loops, timing-based mileage awards, a finisher medal, and an on-site meal and after party.

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.