Trail Running calendar near Winchester 2026-2027

Experience the inaugural Howlin' Wolfe 25k or 50k at Natural Bridge State Resort Park. Run through Red River Gorge on a mix of single track trails and fire roads while supporting local search and rescue teams.

Test your endurance at this 4 mile Kentucky obstacle course featuring over 25 challenges like the Warped Wall and Mud Pit. Your participation helps fund scholarships for children to attend summer camp.

Test your limits in the scenic Kentucky Knobs with timed running and rucking challenges ranging from 3 to 24 hours. Enjoy a supportive community atmosphere with loop-based courses featuring waterfalls and historic landmarks.

Experience a historical trail run through Ault Park in Cincinnati. Navigate three miles of winding paths and old pioneer roads with snacks and age graded awards waiting at the finish.

Experience the trails of Cincinnati at the Big Foot Trail Run in Mt. Airy Forest. Choose from four distances including an ITRA indexed 30K and enjoy a community atmosphere with themed medals and costume awards.

Event Details The Wildcat @ General Butler is a trail running event taking place at General Butler State Resort Park in Carrollton, Kentucky. It offers several distance options on a single day. Distances The available trail races are: Half..

Test your strategy and endurance on a 10 km course featuring 18 checkpoints including ziplining and canoeing. Join a team for this unique multi sport challenge on a scenic 575 acre farm in Versailles.

Experience the ridges and meadows of Mt. Airy Forest in this multi distance trail race. Choose between 5.4 or 10.6 miles with early start options for those needing extra time on the scenic counter clockwise loop.

Experience a technical trail race in eastern Kentucky featuring a 10K or a Half Marathon. Navigate wooded terrain with significant elevation gains and fast descents at the scenic Perry County Park in Hazard.

Test your limits at East Fork State Park with a 5K mud run featuring over 15 natural and man-made obstacles. This adventure race offers a challenging course for solo athletes and a dedicated version for families.

Experience the wooded trails and meadows of Cincinnati at French Park. Choose from 5K, 10K, or Half Marathon distances featuring significant elevation and themed costumes in a community trail race atmosphere.

Experience the natural beauty of Green River Lake State Park with several trail distances ranging from a kids run to a half marathon. Join this off road event in Campbellsville for a day of technical climbs and scenic park trails.

Explore Kentucky's trails at the Big Turtle Trail Runs. This untimed event in Morehead offers a 50K and a 10 Miler route on the scenic Sheltowee Trace. Finish by the cutoff to earn your finisher medal.

Explore the scenic grounds of the Loretto Motherhouse on a trail run or walk. The course winds through woodlands, past lakes, and along gravel paths on the property. This event supports the local community and welcomes participants of all p..

Experience a 3.6 mile trail run at French Park featuring meadows and multiple creek crossings. This fourth leg of the Dirt Days Trail Series offers age graded awards and random door prizes in a picturesque Cincinnati park.

Experience a unique trail run on private property in the Red River Gorge with 5K and 10K options featuring significant climbs and views of natural arches.

A trail event at Mount Airy Forest offering 5K, 10K, a 13.1 mile half-marathon and a 30K course of three 10K loops. Walkers are welcome, all finishers receive a themed medal, and series points and youth discounts apply.

Evening cross country races of 5k and 10k at Masterson Station Park on July 24, 2026, with music, food trucks and bourbon tastings. The 5k allows walkers and the 10k has a 16 minutes per mile cutoff.

Experience the natural beauty of French Park in Cincinnati with this trail race featuring wooded paths and creek crossings. Finishers receive themed medals and can compete for points in a season-long trail running series.

Experience the original event of the Dirt Days Trail Series at East Fork State Park. Run through densely wooded trails on a 5.6 mile or 10.8 mile course with options for early starts and various participation categories.