Trail Running calendar near Prospect 2025-2026

Join the inaugural Operation Freedom Run: Wilmore 5K Run & Ruck on Nov 1 for a spirited run or walk across mixed asphalt and cross country terrain. Hosted with Thomson Hood Veterans Center, proceeds benefit the Wounded Warrior Project.

Experience the county's first ultra trail run at O'Bannon Woods State Park on November 1, 2025, with rugged single track, rocky sections and forested hills. Choose distances from a 5K to a 50K and enjoy marked trails, aid station support an..

Push your limits on a rugged trail loop at Deam Lake SRA on November 2, 2025, with 6 and 12 hour endurance options or a single lap fun run. Spots are limited to under 50; entrants get a Lake Vista cap and finishers earn a medal and prizes.

Run the Dirty Dog Trail 4 Miler on November 8, 2025 at Veterans Park in Lexington. Scenic and technical 4 mile trails with roots, rocks and creek crossings, offered in person or virtual. Proceeds support Hickman Creek Conservancy.

Challenge yourself on scenic trails around Deam Lake with choices from a 6 mile or 12 mile run to a 4 hour endurance option. All finishers earn awards and the race is part of the Winter Warrior series for extra bragging rights.

Join Turkey Trails at Sawyer Point Park in Cincinnati on November 16 for fun runs for the whole family, from Kids Dash to 10k plus a virtual option. Enjoy race shirts, medals, and scenic riverfront routes with awards for 5k and 10k finisher..

Southern Lights Stroll 5K is a festive evening event at the Kentucky Horse Park in Lexington, Kentucky. The lineup includes a 5K chip-timed Run and an untimed 5K Stroll, open to participants aged 7 and up. A newly redesigned route guides wa..

Tackle rugged singletrack at the JMF Trails Hillbilly Half, a scenic trail half marathon through Louisville's Jefferson Memorial Forest on November 22. Expect challenging climbs, forest views, and friendly aid stations to keep you moving.

Hit the trails at the Harrods Creek Trail Bash with scenic 5K and 10K loop options through meadow and single track. Enjoy a community run that supports park upkeep and snag a long sleeve tee with early registration.

The Run Empowered Series will take place in Cincinnati on Monday 1 December 2025.

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.

Jackson County Ultras in Brownstown, Indiana is a rugged trail through Jackson Washington State Forest with steep climbs, ridgetop views and laps past two lakes. Options from 10 mile to 100K and relays with custom buckle and medal finishes.

Run the Crooked Creek 5K Trail Challenge on December 6 and 7 at Camp Crooked Creek, a scenic 5K through rolling woods and around John Barr Lake. Top finishers earn awards and every finisher claims a custom Crooked Creek medal.

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.

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.

Run the Etown Trail Classic on March 7, 2026 at Buffalo Lake in Elizabethtown, Kentucky. Choose a 5K, 8 hour solo challenge or team relay on scenic lakeshore and woodland trails with aid stations, chip timing and finisher swag.

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.