Trail Running calendar near Gravel Switch 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.

Take on the Dirty Dog Trail 4 Miler at Veterans Park in Lexington for a scenic creekside trail run with rooted and rocky sections. Virtual entries include a long sleeve shirt and proceeds benefit the 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.

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.

Join the Pilgrimage in the Park 5K on November 27, 2025 at Pulaski Park in Nancy KY for scenic new trail terrain and views of Lake Cumberland. A family friendly fun run rounds out the day and proceeds benefit the American Cancer Society.

Celebrate the season at Christmas at the Camp at Laurel Lake Baptist Camp with a 5K road run or walk, 10K trail race and kids fun run. Enjoy festive decorations, hot cocoa and cookies while supporting the camp and honoring its legacy.

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.

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.

Hit the trails on January 3, 2026 in Nancy, Kentucky for the Frozen Nuts Trail Run, with a half marathon, 10K, 5K and a competitive 5K walk. Enjoy scenic trails, friendly competition and post race camaraderie.

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 scenic Buffalo Lake loop in Elizabethtown at the Etown Trail Classic, with mixed trails and options from a 5K to 8 hour endurance races. Expect aid stations, chip timing, medals, swag and post race snacks.

Join Lucky O'possum in Nancy, Kentucky on March 21, 2026 for scenic trail races and a competitive 5K walk. Choose from a half marathon, 10K or 5K and enjoy great trails and community spirit.

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.