Trail Running calendar near Owensboro 2026-2027

A charity 5K and virtual 5K at River Front Park in Brandenburg supporting an 11 year old boy with a serious brain injury; proceeds will help cover medical and out of pocket treatment expenses.

An obstacle and trail running event at Diamond Lake Resort in Owensboro, Kentucky, featuring 5K and 10K options, 28 obstacles, and youth races for ages 4 to 13. Proceeds benefit MentorKids Kentucky.

Participate in a 5K or 10K trail and ruck run in Velpen to honor veterans and emergency personnel. Enjoy a professionally timed race at Cool Springs that supports local community safety and veteran awareness.

A two-day trail running and mountain bike weekend at McDougal Lake in Hodgenville, KY, featuring distances from 4 to 32 miles, junior and e-bike divisions, looped courses, and a Double Down multi-event option.

A 12 hour trail event at Saunder Springs Nature Preserve in Radcliff, Kentucky, offering solo, two person, and four person team options on a loop course that mixes technical and runnable trail with waterfalls and creekside sections.

A muddy 3 mile obstacle run at Phil Moore Park on August 29, 2026, with 20 or more obstacles and a free kids play area.

Set on the Adventure Trail at O'Bannon Woods State Park on Sept 19, 2026, this event offers 50-mile (solo or relay), 50K and 25K options on rolling technical singletrack. Camping and on-site lodging are available, with aid stations and fini..

Honest Abe Trail Run at Lincoln State Park offers marathon, 14K and 5K courses on trails and roads with aid stations, drop bag support for marathoners, tiered entry fees, and no participant cap.

A running event in Iroquois Park with an approximately 7.5 mile Lookout course and a 3.4 mile Short Loop option. Finishers receive medals and shirts are available by preorder with limited race day sales.

A 24-hour endurance event at Bowling Green Hot Rods Baseball Park on September 26, 2026, run on a 0.31-mile concourse loop. Solo and four-person relay formats, full overnight aid station, finishers' medals, shirts and awards including a 100..

Experience a scenic trail run through the hills of Kentucky at the historic Bill Monroe Homeplace. This event features 5K, 10K, and 25K distances accompanied by live bluegrass music and on site camping.

A community 5K run and walk at the Warrick Humane Society with timed and untimed options, awards, pet bandanas and donation rewards.

On October 24, 2026, the New Hope Wesleyan Ultra Trail Run offers four trail distances at O'Bannon Woods State Park, featuring single-track forest trails, rocky sections, notable elevation changes, aid stations, timing, and awards for top f..

Two trail races, 50K and 25K, take place at Mammoth Cave National Park on October 24, 2026 starting from Bell's Tavern Pavilion. The crushed gravel out and back course has ascents and descents, cupless aid stations, and limited entries.

A Thanksgiving-themed chip-timed 5k at Turtle Run Winery in Corydon, IN, on November 7, 2026, featuring wine pours and event items including a t-shirt, collapsible wine glass, and a finisher medal that doubles as a wine stopper.

Experience an exclusive trail event at the Harry S. Frazier Scout Reservation featuring looping courses through Kentucky forest and a runner's village by John Barr Lake with distances from 5K up to 100 miles.

A winter event in Bowling Green on January 2, 2027 offering a 4 mile run (two laps on a gravel perimeter track) and a 2 mile walk with walking only rules. Entry fee is $40 and each paid participant receives a sweatshirt or hoodie.

Experience an endurance challenge at Elizabethtown Nature Park featuring an 8 hour race and a 5K trail run. Navigate a scenic loop of lakeside trails and rolling woodland terrain with full aid station support.