Trail Running calendar near Shepherdsville 2025-2026

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..

Sorta Mountain Stage Race, held in Borden, Indiana, offers several Knobstone Trail distances: 5-mile, trail half marathon, 18-mile Ultimate 18, and a new 50K option. The 5-mile course is a loop with a turnaround at mile 2.5; the half is out-and-back to the summit of Round Top Knob; the 18-mile cours..

Pride Run Lexington is a LGBTQ+-supporting running event produced by Frontrunners Lexington, held at Coldstream Park on the grounds of the Kentucky Horse Park in Lexington, Kentucky. The weekend event offers a 5K Run/Walk on scenic trails (chip-timed) and a 1 Mile Fun Walk, plus a volunteer option...

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..

Run Baby Run 5K Benefiting NICU Babies is Lexington, Kentucky’s race held at Coldstream Park/Legacy Trail. The in-person 5K Run/Walk, a Kid’s Dash (1/4 mile) for children 10 and under, and a 5K Virtual Participant option make up the events. The flat, fast course follows the Legacy Trail through Cold..

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..

6 Hours of Power at General Butler State Park (Recreation Center) in Carrollton, Kentucky, is a Wolf Pack Adventures endurance event. Runners complete as many 5K loops as possible within a 6-hour window, with a minimum four-loop finish to officially complete the race. The course is a single 5K loop..

Run The Ridge Trail Race in Beaver Dam, Kentucky offers three trail distances: 5K, 10K, and 25K. The course climbs high in the hills and winds along dirt roads and ridge overlooks, with steep ascents and descents to reach the ridge top and return. The race starts and finishes at the celebrated Bill..

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..

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 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..

New Hope Wesleyan Ultra Trail Run, Harrison County's first ultra marathon, is held at O'Bannon Woods State Park in Corydon, Indiana. The event offers four trail distances: a 50K ultramarathon (two 13.5-mile loops plus a 4-mile loop, about 3,500 ft of elevation), a half marathon (13.1 miles, ~1,500 f..

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 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 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..

Crooked Creek Ultra Trail Race unfolds at Camp Crooked Creek in the Harry S. Frazier Scout Reservation near Shepherdsville, Kentucky, in Bourbon Country. The centerpiece is a demanding 12.7-mile loop with about 2,300 feet of elevation gain, winding through 1,000 acres of hardwood forest and abundant..

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