Trail Running calendar near Shepherdsville 2025-2026

The 5th Annual Honor and Remember Run in Velpen, Indiana, is a family-friendly event held at Cool Springs, featuring a 5K Run/Walk, a 10K Trail and Ruck Run, and a Virtual Run option. This race honors military veterans, their families, emergency personnel, and those who died on 9/11 and subsequent w..

The OCHS XC Fundraiser 5K is a cross country running event held at Yellow Creek Park in Owensboro, Kentucky. It features two race distances: a 5K and a 3K cross country course, both run on the same course used by local high school teams. This event supports the Owensboro Catholic High School Cross C..

The Blackacre Barnstormer will take place in Louisville on Sunday 24 August 2025. You can run between 4 and 8 miles.

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 Honest Abe Trail Run is held at Lincoln State Park in Lincoln City, Indiana, offering marathon, 14K, and 5K distances. The marathon consists of three loops around the park, while the 14K is a single loop, primarily on double-track trails with some gravel and road crossings. The 5K course runs on..

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 Run The Ridge Trail Race, held in Beaver Dam, Kentucky, offers 5K, 10K, and 25K trail running events along scenic dirt roads and overlooks once traveled by bluegrass legend Bill Monroe and his Uncle Pen. The challenging course features steep inclines and declines as runners ascend and descend th..

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 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 Mammoth Cave 50K/25K is a trail running event held in Mammoth Cave National Park, Park City, Kentucky. Scheduled for October 25, 2025, it features two distances: a 50K and a 25K. The race takes place on the scenic Bike & Hike Trail, a crushed gravel out-and-back route named after a historic rail..

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 covering a 4.167-mile loop. The course features challenging terrain with a steep summit climb o..

The Deam Lake Winter Warrior will take place in Borden on Sunday 9 November 2025. You can run between 6 and 4 kilometers.

The JMF Trails Hillbilly Half is an annual challenging half marathon held at Jefferson Memorial Forest in Louisville, KY. The 10th edition features a rugged trail course starting at the Horine parking area, looping around a lake, descending Yost Ridge Trail to the Welcome Center, then following the..

The Crooked Creek Ultra Trail Race will take place in Shepherdsville from Saturday 6 December 2025 to Sunday 7 December 2025. You can run between 13 and 100 miles.

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..