Trail Running calendar near Urbana 2025-2026

Limestone Rocks! 8-Hour or 4-Hour Race takes place at Limestone Park in Kankakee, Illinois. Runners choose an endurance 8-Hour or a 4-Hour option, competing on a 1.65-mile loop course. The surface is mostly crushed limestone with sections of asphalt; the course is roughly half flat and half hilly, f..

Run The Woods is a charity running event held in Hudson, Illinois at Timber Pointe Outdoor Center (20 Timber Pointe Lane). The series includes 5K, 5K for Youth, 8K, 8K for Youth, and a 1 Mile Trail Walk – Untimed. While the site doesn’t describe a specific course layout, the venue suggests a family-..

Shake Your Trail Feather Trail Run takes place at Willenborg Woods in Charleston, Illinois, offering four distances: 50K, 16-mile, 8-mile, and 5K to suit a range of trail runners. The course uses true trail terrain with single-track paths through timber, grassy riverside segments, creeks, and hills,..

Oktoberfest Rotary Run is an annual fundraiser in Bloomington, Illinois, held on the third Sunday each October. The event centers at GE Park / Union Park Clubhouse (1750 GE Road) and offers a chip-timed 5K on the Constitution Trail, looping through Tipton Trails and returning on blacktop paths. A 1‑..

The Allerton Park Trail Run, hosted by Second Wind Running Club, takes place at Robert Allerton Park and Retreat Center in Monticello, Illinois. The event features a challenging 5.7-mile trail run along the Sangamon River, known for its hidden roots, ruts, and sharp turns, as well as a 2-mile nature..

Rattlesnake Master Run for the Prairie is a community running event in Urbana, Illinois, at Meadowbrook Park. The 27th annual edition features a 10K Run, a 5K Run, and a 5K Walk, plus 5K and 10K Virtual Races for remote participants. The course circles Meadowbrook Park’s 130-acre prairie and include..

On the Move for Men's Health 4-Hour Endurance Challenge takes place at Ballard Nature Center in Altamont, Illinois, on a 5K wooded trail loop with rolling hills. Runners aim to complete as many laps as possible in four hours, with breaks in the Trail Village. The race offers special divisions for we..

Da Deer Run Run is an 8K cross-country trail race at Timber Pointe Nature Center in Hudson, Illinois. In its fifth year, the course features two loops through Timber Pointe, using wide double-track trails with some gravel, and nods to sections of the Run the Wood Race in October with twists. The eve..

Set in Kickapoo State Recreation Area, Oakwood, Illinois, the Siberian Express Trail Race is a 7.45-mile, 95% trail course that winds east from the park into woodlands, featuring steep hills, creek crossings, and wildlife sightings. The event emphasizes a wintry Midwest experience, with a time limit..

The Hawthorn Half Day Relay & Ultra, held in Terre Haute, Indiana, is a unique endurance event established in 2006, celebrating its 20th anniversary in 2026. Participants can choose between 6-hour or 12-hour races on a scenic 5K loop combining trail and road, with a shorter ½-mile course available n..

Elsa Chicken Plucker Backyard Ultra is a Bronze Ticket Event held at Willenborg Woods in Charleston, Illinois, on 149 acres of lovingly maintained trails. Runners tackle a 4.167-mile loop every hour, with the last athlete standing earning a Bronze Ticket toward Big Dog’s Backyard Ultra World Champio..