Trail Running calendar near Shelbyville 2025-2026

The Indian Trails 5K is a fundraising running and walking event held in Milan, Indiana, supporting the Milan cross country team. Scheduled for August 2, 2025, it offers multiple participation options including 5K runs and walks, with or without a commemorative t-shirt. The race is part of the Southe..

The Talon's Trail to Triumph 5K is a charity running event held in Brandenburg, Kentucky, at River Front Park. Scheduled for August 2, 2025, the event features a 5K run/walk, a free kids' run for ages 12 and under, and a virtual 5K option. The race supports the family of Talon Lopez, a 10-year-old b..

The Blackacre Barnstormer is a trail running event held at Blackacre Nature Preserve in Louisville, Kentucky. Scheduled for August 24, 2025, it features two race distances: a 4-mile and an 8-mile course. The scenic route starts near the historic Tyler Homestead and barn, winding through fields and t..

The Cabernet Canter Cross Country 5K/10K is an annual running event held at Talon Winery in Lexington, Kentucky. Participants can choose between a 5K or 10K cross-country race through the scenic winery grounds. Each runner receives a race shirt and a Cabernet Canter wine glass, with a complimentary..

The Sorta Mountain Stage Race, held in Borden, Indiana, offers multiple trail running distances including a 5-mile, half marathon, 18-mile "Ultimate 18," and a new 50K option combining the half and Ultimate 18 courses. The race takes place on the rugged, single-track Knobstone Trail featuring rocky,..

The Heartland Harvest Festival 5K is a scenic autumn running event held at Elizabethtown Nature Park in Elizabethtown, Kentucky. Scheduled for September 27, 2025, this light trail 5K race offers a welcoming atmosphere for both seasoned runners and newcomers. Participants can enjoy the natural beauty..

The Raven 10K is an annual trail running event held at Raven Run Nature Sanctuary near Lexington, Kentucky. This scenic 10K race takes place on the sanctuary's 734-acre grounds, featuring trails through meadows, woodlands, and streams, with historic early 19th-century settler remnants along the rout..

The General Butler Trail Race, held at General Butler State Resort Park in Carrollton, Kentucky, offers a variety of trail running events including a half marathon, 10K, 5K, 20K relay, and a unique 6 Hours of Power endurance challenge. The courses start and finish at the park's Recreation Center, fe..

The Deam Lake Loop Trail Run is an inaugural event held at Deam Lake State Recreation Area in Borden, Indiana. Scheduled for October 4, 2025, it features 10K and 5K trail races as well as 10K and 5K trail walk/hike options. The 10K course follows the scenic Deam Lake Loop trail, offering a moderatel..

The Forkland Festival Fox and Hound 4K is a unique trail running event held in Gravel Switch, Kentucky, within the scenic Forkland Community. This challenging 4-kilometer course features a steep quarter-mile uphill start, followed by open meadows and woodland trails, finishing with a downhill stretc..

The West Side, Best Side 5K Trail Run is part of the Dirt Days Trail Series held at Shawnee Lookout Hamilton County Park in North Bend, Ohio. This scenic trail run covers approximately 3.44 miles (5.54 km) combining the Blue Jacket and Little Turtle nature trails, offering breathtaking views of the..

The Camp Challenge 5k Trail Run takes place in Bedford, Indiana, set amidst the scenic woods of Southern Indiana. This challenging 5-kilometer race features a rugged course with steep inclines and thrilling descents through wooded trails, offering a true test of endurance. Beyond the physical challe..

The Stone Steps 50K and 27K Trail Run is a long-standing ultra marathon event held in Mt. Airy Forest, just outside downtown Cincinnati, Ohio. Celebrating over 20 years, it offers two distances: a challenging 50K ultra marathon and a 27K fun run.The course features rugged single-track trails through..

The New Hope Wesleyan Ultra Trail Run, held at O'Bannon Woods State Park in Harrison County, Indiana, is the area's first ultra marathon trail event. Scheduled for November 1, 2025, it offers four race distances: a rugged 50K ultra featuring two 13.5-mile loops plus a 4-mile loop with about 3,500 fe..

The Lake Vista Lunatics Run is an endurance trail running event held at Deam Lake State Recreation Area in Borden, Indiana. Participants can choose between 6-hour and 12-hour runs, or a single-lap fun run of 4.167 miles. The course features a challenging loop with a steep summit climb of 25-30% grad..

The Deam Lake Winter Warrior is a running event held at Deam Lake in Borden, Indiana. It features three race options: a 6-mile run, a 12-mile run, and a 4-hour endurance run around the scenic Deam Lake Loop. This event is part of the Winter Warrior Series, designed to keep runners motivated through..

The Run Empowered Series, held in Cincinnati, Ohio, is a dynamic running event series organized by Empower Ultras. Participants can choose from a variety of race distances, including 10K, 15 miles, marathons, and ultra-distance events like 48-hour and backyard ultras. The series encourages runners t..

The Crooked Creek Ultra Trail Race takes place at Camp Crooked Creek within the Harry S. Frazier Scout Reservation in Shepherdsville, Kentucky, set in scenic Bourbon Country. The event features a challenging 12.7-mile loop with over 2,300 feet of elevation gain per lap through 1,000 acres of hardwoo..

The Jackson County 50-50 Ultramarathon, held in Brownstown, Indiana at the Pyoca Camp and Retreat Center, offers challenging trail races including 10-mile, 50k, 100k, and a 100k relay. The course features rugged terrain with steep topography, rewarding runners with scenic vistas around two lakes and..

The Crooked Creek 5K Trail Challenge is a unique running event held at the Harry S. Frazier Scout Reservation in Shepherdsville, Kentucky. Taking place over two days in early December 2025, this 5K trail race offers participants a chance to experience a challenging course winding through over 1,000..