Trail Running Calendar Kentucky 2026-2027

Shelby Trails in Simpsonville KY on January 17 offers scenic 4 mile and 8 mile looped courses with creek crossings, rows of cedars, single track and rolling hills. Varied trail and open pasture sections make for a rewarding challenge.

Louisville Lovin' the Hills invites trail lovers to Fairdale KY on February 7, 2026 with 50K, 15 mile and 6 mile options across scenic single track forest trails. Enjoy pre race pasta, wooden medals, post race soup and a friendly race vibe.

The Warbird 100 is a 103 mile mountain ultra through Daniel Boone National Forest featuring rugged ridgelines, technical singletrack and creek crossings. Expect remote trails, big climbs, exposed views and a 35 hour cutoff.

Run scenic single track along Kentucky Lake and Lake Barkley at the Land Between the Lakes Great American Trail Race in Grand Rivers, KY on March 14, 2026. Choose from 23 km to 50 miles across rolling looped trails with a 12 hour limit.

Hit the trails at Lucky O'possum on March 21, 2026 in Nancy, Kentucky. Choose a half marathon, 10K or 5K trail run for a fun day of challenge and community.

Bourbon Country offers 25k, 50k and trail 5k on March 28 in Shepherdsville Kentucky, set on 1,000 acres of rolling, hilly terrain. Pick a challenging loop or a shorter trail test and finish with a race shirt and medal.

Hit the 99% singletrack at Saunders Springs for a day of trail running and mountain biking on scenic preserve trails. With distances and team formats for all ages, plus kids races, the event benefits local trail groups.

Run the inaugural Howlin' Wolfe 25k and 50k through scenic Red River Gorge on April 11, 2026, starting and finishing at Natural Bridge State Resort Park. Trails mix road, single track and fire road with staffed aid stations.

Run the Dirt Days Trail Series at Ault Park on April 19, 2026 a scenic 3.6 mile rolling trail that winds past an old railroad trestle and along an old pioneer road. Chip timing, refreshments and age graded awards make this a fun community r..

Run the Backside Trail Marathon and Half in Louisville on April 26, 2026, on gently rolling single track through Seneca and Cherokee Parks. Finishers get medals and a rewarding wooded trail experience.

Run the trails at General Butler State Park on May 2, 2026 for The Wildcat, a scenic trail race offering 5K, 10K, 1/2 marathon, 20K relay and a 6 Hours of Power event. Enjoy river overlook views, custom medals and on course aid.

The Laurel Lake 10k will take place in London on Saturday 9 May 2026. You can run 45 miles.

Run the scenic Mt. Airy Forest trails on May 17, 2026 with 5.4 Mile and 10.6 Mile loop options through hills, ridges, streams and meadows. A casual Trekker entry gives recorded time and extra finish time for a relaxed trail experience.

Join Gavin's Gallop, a scenic 5K at Freeman Lake Park in Elizabethtown that follows a lakeside out and back trail with a water stop at the turnaround. All finishers earn a medal and proceeds support Gavin’s Gifts for families affected by Ba..

Hit the trails at French Park for a scenic 3.6 mile dirt trail run featuring creek crossings, meadow views and log bridges. Enjoy age graded awards, random Altra shoe giveaways and season pass options for the full Dirt Days series.

Enjoy a scenic 5K trail run at Natural Bridge Campground in Red River Gorge on Saturday, June 27, 2026. Celebrate with shirts, music, food and finish line photos while tackling this beautiful wooded course.

Run through scenic trails at Talon Winery with 5K and 10K cross country courses, then celebrate with live music and a tasting. All finishers get an award and adults receive a drink ticket for one glass of Talon wine.

Join the Spoonbread Festival 5K in Berea, Kentucky on September 20 for a friendly flat and fast run or a relaxed 1 mile fun walk along the scenic Berea City Trail. Enjoy chip timing, commemorative shirts, music, food and a water stop while..

Run Baby Run 5K returns to Lexington's Coldstream Park and Legacy Trail with a flat, fast course and a Kid's Dash for young runners. All proceeds support the Snow Bunny Baby Project to buy diapers and wipes for NICU families.

Hit the trails at the Yeti Trail Run in Mount Airy Forest Cincinnati with 5K, 10K, half marathon and 30K options through meadows, woods and along a fossil creek. Finishers get medals, costumes are encouraged and walkers are welcome.