Trail Running calendar near Shepherdsville 2026-2027

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.

The Kentucky Cryptid Series - Wolfman is a trail run through Iroquois Park, offering 7-mile and 4-mile options. It's part of a four-race series where completing three earns a special survivor medal and shirt. This cupless event encourages p..

Experience a women only 5K obstacle mud run at Pop's Landing at Haddix Farms. Join a community focused on unity and empowerment while tackling a fun mud course to support breast cancer awareness.

Run for 12 hours on a scenic loop course through Saunder Springs Nature Preserve. Choose to tackle the trails solo or as part of a two or four-person team. The challenge is to cover as much distance as possible on terrain featuring forests,..

Experience a cross country race through the scenic grounds of Talon Winery in Lexington. Enjoy a finisher award plus a glass of wine and live music at the post race celebration.

Experience a unique trail race through the historic Blackacre Nature Preserve featuring wooded paths and farm animal sightings. Choose between 4 or 8 mile distances and enjoy post race ice cream at the historic homestead.

A stage trail race on the Knobstone Trail near Borden, Indiana offering 5 mile, half marathon, 18 mile and 50K options with rugged single track, aid stations and proceeds to the SAM'S Foundation.

Explore Lincoln State Park on trails and gravel roads. Choose from a marathon, 14K, or 5K distance, all starting together. The event features a scenic loop course with aid stations and a focus on environmental responsibility.

Run, walk, or volunteer at the Run Baby Run 5K to support NICU babies. This flat course on Lexington's scenic Legacy Trail includes a kids' dash and virtual options. All proceeds purchase supplies for families in neonatal intensive care uni..

Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.

Enjoy scenic 5K and 10K trail runs or walk and hike options at Deam Lake in Borden Indiana on October 3, 2026. Expect rolling climbs, creek crossings, multi use trails and reusable cupless aid stations for a sustainable race.

Honor history at the Mogadishu Mile, a four person team obstacle course and one mile ruck run in Georgetown. Work together to complete 500 total reps and a weighted run without leaving any team member behind.

Run through the scenic trails of Jefferson Memorial Forest in this cupless trail event featuring 5 mile and 8 mile distances. Earn special series awards while exploring the beautiful Horine Reservation landscape.

Experience a unique trail run through the hills and woodlands of Gravel Switch. Enjoy a route featuring meadows and steep climbs followed by a pancake breakfast and handmade awards at the local heritage festival.

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.

The Little Rooster Run offers a weekend of trail events in Glencoe, Kentucky, from a kids' fun run to a 5K and the unique Mini Barnyard Ultra. This "last runner standing" format challenges participants on a 2-mile loop every half hour. Proc..

Join the second annual Running Pumpkin 5K in Lexington's Coldstream Park. This fall event supports Gleaning Housing, a local nonprofit building affordable rental homes. Participants are welcome to bring a pumpkin or wear a costume, with sna..

An endurance trail event at Deam Lake SRA with 6 hour, 12 hour and a one-lap fun run on a 4.167 mile loop featuring a steep summit and technical sections. Limited entry, finisher medal and a baseball cap included with registration.

The Deam Lake Winter Warrior kicks off a trail running series at Deam Lake in Indiana. Choose from a 6-mile, 12-mile, or 4-hour endurance run on the scenic Yellow Trail loop. It's a cupless event where all finishers get an award.

Jackson County Ultras in Brownstown, Indiana on Dec 5, 2026 offers trail races from a 10 mile to a 100k of about 62 miles on a rugged, clockwise course, with weekend lodging, well stocked aid stations and live tracking for the 100k and rela..