Trail Running calendar near Freeport 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.

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..

Test your endurance at this 24 hour track event in Davenport where you can run or walk at your own pace. With a limited field of 60 participants, every runner receives a shirt and personal lap counting support.

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.

Trail run in Dubuque on May 2, 2026 offering 5K, 10K and half marathon distances. The event features marked trails, basic timing, a custom bib, a rotating race item, and post-race food; series entry includes a series gift.

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 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.

Trail races at Sunderbruch Park in Davenport on May 16 2026 with 5K and 10K routes on mostly single track dirt trails. Online registration and a waitlist are used and no refunds are offered.

Big Climb Wisconsin on May 16, 2026 in Madison is a team-based stadium climb that features stairs, ramps, and concourses. The event honors patients and survivors and awards participants a finisher medal while supporting efforts against bloo..

Rail-trail event in Belleville, WI using the Badger State Trail and Sugar River State Trail. Distances include 50 miles, 50K and a half marathon on flat, soft surfaces with trestle bridges and a quarter mile tunnel.

Test your grit at Byron Motosports Park with tactical obstacle courses ranging from 5K to 10K endurance laps. Choose from elite vest challenges, weighted rucking, or open waves designed to honor the resilience of first responders.

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.

Blue Mound Trail Run on June 6, 2026 in Blue Mound State Park features 10K and 18K trail races on single-track and ski trails, and serves as a fundraiser for Friends of Blue Mound State Park.