Trail Running calendar near Wilmore 2025-2026

The Shelby Trails event in Simpsonville, KY, features two trail running races: a 4-mile and an 8-mile course. Scheduled for January 25, 2025, the event is designed to accommodate both beginners and experienced runners, offering a mix of technical terrain, hills, and scenic landscapes. The 4-mile rac..

Louisville Lovin' the Hills is a challenging running event held in Fairdale, KY, featuring a 50K, 15-mile, and 6-mile race. Established in 2004, the race takes participants through scenic single-track trails divided into three parts, making it one of the toughest 50Ks in the region. The event includ..

The Etown Trail Classic is a running event scheduled for March 1, 2025, in Elizabethtown, Kentucky. This exciting event features multiple race options, including an 8 Hour Endurance Race, an 8 Hour Endurance Race Relay, and a 5K Trail Run, catering to various levels of runners. Participants can enjo..

The Wildhorse Ultra is an exciting running event taking place in Georgetown, Kentucky, at Scott County Park. Participants can choose from various race durations, including 12, 8, 6, 4, and 2-hour options, as well as a free Kids Dash. The course features a 1-mile loop, encouraging runners to complete..

The Lucky O'possum is an exciting running event taking place in Nancy, Kentucky, featuring a variety of trail races. Participants can choose from a 5K Trail Run, a 10K Trail Run, a Half Marathon Trail Run, and a 5K Trail Walk, catering to different fitness levels and preferences. This event promotes..

The Bourbon Country 25K/50K is an exciting trail-running event scheduled for March 29, 2025, at the Harry S. Frazier Scout Reservation in Shepherdsville, Kentucky. This race offers participants the choice between two distances: a 25K and a 50K, both set against the picturesque backdrop of Bourbon Co..

The Red River Gorge Ultra is a premier trail running event held in the scenic Red River Gorge of Kentucky. Scheduled for April 5-6, 2025, it features a challenging 50K race on Saturday and a 25K race on Sunday, attracting runners from across the region. Since its inception in 2015, the event has bec..

The Red River Gorge Ultra is an exciting running event taking place in Pine Ridge, Kentucky, featuring two main race distances: a 25K and a 50K. Scheduled for April 5-6, 2025, this event invites runners of all levels to experience the stunning natural beauty of the Red River Gorge area. Participants..

The Big Turtle 50 Miler is an exciting trail running event taking place in Morehead, Kentucky, featuring three race distances: a challenging 50-mile race, a 50K for those looking for a shorter ultra experience, and a 10-mile option for beginners. The 2025 edition introduces a new start and finish li..

The Backside Trail Marathon, held in Louisville, KY, offers both a full marathon and a half marathon, taking place in the scenic Cherokee and Seneca Parks. Established in 2012, this event encourages participants to enjoy the trails following nearby road races, making it a unique "Double Down" opport..

The Many Miles 4 Malakai 4x4x48 Challenge is a unique running event taking place in Lexington, KY, designed to raise awareness and funds for children affected by gun violence. Participants can join individually or as teams, running 4 miles every 4 hours for a total of 48 hours, culminating in 48 mil..

The Blackacre Barnstormer is a trail running event taking place at the Blackacre Nature Preserve in Louisville, KY. Participants can choose between two distances: a 4-mile and an 8-mile race, both designed to showcase the scenic trails and wildlife of the area, including goats and cows. The event su..

The Cabernet Canter 5k & 10k is a running event taking place at Talon Winery in Lexington, Kentucky. Participants can choose between a 5k or 10k race, both set against the scenic backdrop of the vineyard. This event is designed to provide a fun and engaging experience for runners of all levels, allo..

The Raven 10K is an annual trail running event held at the Raven Run Nature Sanctuary in Lexington, Kentucky. Scheduled for September 28, 2025, this race features both an in-person 10K and a virtual option for participants who prefer to run on their own schedule. The in-person race has a registratio..

The Heartland Harvest Festival 5K is an exciting running event set in the picturesque Elizabethtown Nature Park. Scheduled for September 30, 2025, this trail race welcomes participants of all skill levels, from seasoned runners to newcomers. The event features recognition for the top three overall m..

The Rugged Red Trail Half Marathon is an annual running event held in Slade, Kentucky, featuring a scenic 13.1-mile looping trail course in the picturesque Red River Gorge. Scheduled for October 4, 2025, this race not only celebrates the beauty of trail running but also supports local search and res..

The Crooked Creek Ultra Trail Race is an exciting trail running event held at Camp Crooked Creek in Shepherdsville, Kentucky. Set against the backdrop of Bourbon Country, the race features a challenging 12.7-mile loop with over 2,300 feet of elevation gain per lap, offering participants stunning vie..