Trail Running calendar near Louisville 2026-2027

Event Overview The Indian Trails 5K is a 5K running and walking event scheduled for Saturday, August 1, 2026, in Milan, Indiana. The event is the fourth race in the Southeastern Indiana Racing Circuit (SIRC), a summer series of five 5K race..

This charity 5K run and walk supports Talon Lopez, a 10-year-old with an anoxic brain injury. The event offers in-person and virtual options, plus a free run for kids 12 and under. It takes place at River Front Park in Brandenburg, Kentucky..

A community event in Velpen, IN on August 8, 2026 featuring a 5K, a 10K trail and ruck run, plus a virtual option. Proceeds support local police and the event honors veterans, emergency personnel and those lost on 9/11 and after.

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..

The Cabernet Canter Cross Country 10K is held at Talon Winery in Lexington. Participants run a cross-country course and receive a finisher's award with a glass of wine. An after-party with live music follows the race.

The Sorta Mountain Stage Race offers three distances on September 13, 2026. Choose from the Ultimate 18, a Half Marathon, or a Five Miler course. All registration is managed through Ultrasignup.

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..

A trail 10K at Raven Run Nature Sanctuary in Lexington on September 27, 2026, offering an in person field limited race and a virtual 10K with mailed shirts and no results submission.

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.

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.

A trail run on October 10, 2026 in Gravel Switch, Kentucky. The 4K course winds through hills, meadows and woodland and includes a pancake breakfast plus handmade awards presented at the community shelter.

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..

Celebrate the 24th annual Tecumseh Trail Challenge Festival in the autumn colors of Yellowwood State Forest. Choose from five classic trail distances, from 8 miles to 50k, and enjoy a festival atmosphere with camping, live music, and a comm..

Test your endurance at this 6 hour trail challenge where you must complete a 5 km lap every hour to stay in the race. Finish all six rounds to earn your medal at CERA Sports Park.

Run through the autumn landscapes of Fowler Pumpkin Patch on a scenic trail course. Choose from a 5K trail run or shorter family-friendly distances. Your participation supports local childhood education and food security initiatives.

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.

Experience a rugged trail race in Brownstown featuring 100k, 50k, and 10 mile distances with a 24 hour cutoff and full retreat center amenities.

A two day trail weekend at Camp Crooked Creek near Shepherdsville, KY, using a 12.7 mile loop with over 2,300 ft elevation gain per lap and race options from 5K up to 100 miles on December 5 and 6, 2026.

Trail races at Waverly Park from December 13 to December 27, 2026 offering 6.5 Mile and Half Marathon distances plus virtual options. Part of a Winter Warrior Series with course markings, on-course aid, awards, and a series medal for multip..