Trail Running calendar near Terre Haute 2025-2026

The Wild Wild Wilderness is an annual running event held at Kickapoo State Recreation Area in Oakwood, Illinois. Established in 1981, the race features multiple distances including a 5K and a challenging 7.45-mile trail run that covers steep hills, creek crossings, and scenic woodland terrain. The c..

Ellettsville 5K is a community running and walking event in Ellettsville, Indiana, offering a 5K Run, 5K Walk, and a free 1 Mile Fun Run for kids. The flat, out-and-back course begins at the Karst Trail Head at Route 46 and Hartstrait Roads and runs along the Karst Park Greenway Trail, providing a f..

Hope on the Trail is a running and walking event held in Thorntown, Indiana, featuring 5K and 10K distances along with a "Fun Run" and a "Run your own race!" option for 5K or 10K. Participants enjoy the scenic Farm Heritage Trail, providing a beautiful outdoor course experience. The event supports a..

Oktoberfest 5K Presented by Big Lug Brewing takes place in Indianapolis, Indiana, along the Monon Trail, starting from Big Lug Canteen. It's a 5K run/walk on a fast, flat, shaded route that offers a PR-friendly course. Runners finish with a cold Oktoberfest Festbier and are treated to a post-race Ok..

The Apple Mash Dash Cider 5k Run/Walk is held at Avon Town Hall Park in Avon, Indiana. This 5k course winds through scenic park trails, with portions on unpaved or grassy surfaces. The event is family-friendly and invites participants to dress in costume, offering a trophy for the most creative look..

Tecumseh Trail Challenge is a trail-running festival in Nashville, Indiana, at Yellowwood State Forest, with start/finish at the Jackson Creek Trailhead. Distances include 50K solo and a 50K relay (2-4 runners), plus 26.2, 13.1, and 8-mile options. The festival atmosphere features on-site tent campi..

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,..

Camp Challenge 5k Trail Run unfolds in the wooded hills of southern Indiana near Bedford. The 5-kilometer course traverses rugged, forested terrain with steep inclines and thrilling descents, testing endurance amid natural beauty. The event blends challenge with a mission: all proceeds fund scholars..

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..

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 FroMoMoFo 20 Miler & 10 Mile Fun Run is a winter trail running event held at Morgan Monroe State Forest in Martinsville, Indiana. Participants can choose between a 20-mile race, consisting of two loops, or a 10-mile run, both on the scenic Three Lakes loop trail featuring single-track paths and..

The OPSF 50/50 Trail Race is a well-established event held in Owen-Putnam State Forest near Poland, Indiana, about an hour from Indianapolis. Organized by the Indiana Trail Running Association, it offers multiple distances: a 50-mile ultra, a 50K, a 14-mile run, and a 10K trail race. The course feat..

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..

MoMoFo 100k and 20 mile Fun Run with Virtual Options is held in Martinsville, Indiana, at Morgan Monroe State Forest. The event offers 100-kilometer and 20-mile distances, plus virtual options. The course is 85% single-track, 11% forest service road, and 4% paved road, featuring old-growth forests,..