Trail Running calendar near Simpsonville 2025-2026

Run through hardwood forest and around John Barr Lake at the Crooked Creek Ultra Trail Race in Shepherdsville Kentucky. Distances range from a 5K to a 100 mile ultra with looped courses, support access and heated facilities.

Tackle steep winter trails at Jackson County Ultras, December 6 and 7 at Pyoca Camp in Brownstown Indiana, with 100k, 50k, 10 mile and team relays. The 100k is a Western States qualifier and the venue offers showers, hot meals and optional..

Run a scenic 5K through Camp Crooked Creek’s rolling hills and hardwood forest by John Barr Lake at the Crooked Creek 5K Trail Challenge on Dec 6 and 7, 2025 in Shepherdsville, KY. Enjoy natural trails, a custom finisher medal, and friendly..

Run the Waverly Winter Warrior at Waverly Park in Louisville on December 14, choosing a 6.5 mile trail loop or a half marathon. Part of the Winter Warrior Series, the event rewards every finisher and offers bundle discounts for multiple rac..

Tackle scenic singletrack along Otter Creek in Brandenburg, KY on Dec 20, 2025, with marathon, 16 mile and 8 mile options. Rolling hills, creekside trails, hot food and carved wooden medals make this a cozy winter trail challenge.

Shelby Trails in Simpsonville KY on January 17, 2026 showcases scenic trails through pastures, rows of cedars and wooded creek bottoms. Choose a 4 mile loop or tackle two laps for an 8 mile challenge on mixed grass, dirt and single track.

Run single track forest trails in Fairdale near Louisville on Feb 7, 2026 with 50K, 15 mile, and 6 mile options. Finish with soup and a wooden medal, and enjoy a packet pickup pasta dinner the night before.

Knobstone 50 on April 11, 2026 is a point to point 50 mile trail race through rugged southern Indiana with roughly 10,000 feet of climbing along the Knobstone Trail. Registration closes April 3 and pacers are allowed for the 50 mile field.

Enjoy singletrack trail runs and mountain bike endurance races at Saunders Springs Nature Preserve with solo, duo and team classes plus kids races. Proceeds benefit local trail stewardship and KyMBA programs, so you can race and give back.

Join the Backside Trail Marathon in Louisville's Cherokee and Seneca Parks on April 26, 2026, with marathon or half on scenic single track. Medals for all finishers and a Double Down award for back to back weekend runners.

Hit the trails at General Butler State Resort Park for The Wildcat, with 5K, 10K, half marathon, 20K relay and a 6 Hours of Power. Enjoy lake and river overlook views, custom swag and fully supported aid stations.

Take on the Mt. Airy Ridge Run in Mt. Airy Forest, Cincinnati on Sunday, May 17, 2026, as part of the Dirt Days Trail Series. Choose a 5.4 or 10.6 mile loop through scenic trails, meadows and ridgelines, with on site pickup and Altra shoe p..

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..

Celebrate Father's Day at French Park with the Dirt Days Trail Series. Run a spirited 3.6 mile course of meadows, creek crossings and log bridges with chip timing, prizes and a festive postrace vibe.

Run the rolling grounds of Talon Winery at the eighth annual Cabernet Canter, with scenic 5K and 10K cross country courses. Enjoy finisher awards, a wine ticket and live music while celebrating among the vines.

Celebrate the 30th annual Spoonbread Festival 5K on Sunday, September 20, 2026 in Berea, Kentucky on the flat Berea City Trail. Chip timing, commemorative shirts, music, food and free race photos make this a fun community run.

Join the Run Baby Run 5K in Lexington for a flat, family friendly course through Coldstream Park that supports NICU families. Enjoy a kids dash, commemorative tee and virtual option while helping provide essentials for babies in need.

Experience the Raven 10K through scenic trails at Raven Run Nature Sanctuary in Lexington on Sunday, September 27, 2026. Limited to 170 runners, this 12th annual trail race features performance shirts and custom age group medals.