Trail Running calendar near Simpsonville 2025-2026

Run Otter Creek singletrack in Brandenburg, KY on Dec 20 with marathon, 16 and 8 mile trail runs along a creek with rolling hills and pine needles underfoot. Expect carved wooden medals, a chili cook off and a team marathon.

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.

Louisville Lovin' the Hills in Fairdale, KY on February 7, 2026 offers 50K, 15 Miler and 6 Miler options on scenic single track forest trails. Enjoy pasta at packet pickup, a wooden finisher medal and post race soup with fellow trail runner..

Tackle the Knobstone 50, a rugged 50 mile ultramarathon through southern Indiana's forested Knobstone Trail with roughly 10,000 feet of climbing. Enjoy scenic single track, shuttle service, and a recycled performance hat for all starters.

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.

Enjoy 3.6 miles of winding trails at Ault Park, with a railroad trestle and a stretch of pioneer road providing a scenic, historic backdrop. Chip timing, refreshments, and a friendly vibe make this series stop a great spring outing.

Scenic single track awaits at the Backside Trail Marathon and Half in Louisville's Seneca and Cherokee Parks. The marathon is two loops on gently rolling trails, so wear trail shoes and expect slower times than on roads.

Run The Wildcat at General Butler State Resort Park, a scenic trail race day with options from a 5K to the 6 Hours of Power. Enjoy river overlook views, aid station support and friendly vibes with leashed dogs welcome.

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.

Tackle scenic, hilly trails at Muscatatuck County Park with 15K and 5K options along a river valley. Come for the race and stay for festival camping, mountain bike events and guided kayak trips for a weekend of outdoor fun.

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.

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.

Join the Raven 10K on Sunday, September 27, 2026 for a scenic trail run through Raven Run Nature Sanctuary near Lexington, KY. Choose in person or virtual entry and tackle a challenging 10K in a beautiful park setting with limited field.