Trail Running calendar near Shepherdsville 2026-2027

Experience a scenic trail run through the hills of Kentucky at the historic Bill Monroe Homeplace. This event features 5K, 10K, and 25K distances accompanied by live bluegrass music and on site camping.

A 5K trail run on wooded, hilly camp trails in Bedford, Indiana on 10/10/2026; proceeds fund scholarships to send children to camp. All finishers receive a medal and top male and female receive awards.

A weekend of races at the Gallatin County Fairgrounds in Glencoe, Kentucky featuring an 800 m kids run, a 5K trail with a two hour cut off, and a last runner standing ultra run on repeated 2.083 mile laps. Headlamps required for the ultra.

A second-annual fall 5K hosted by Gleaning Housing at Coldstream Park / Legacy Trail in Lexington, KY, with pumpkins for donors and snacks and drinks for all participants. Participants may bring or wear a pumpkin costume.

On October 24, 2026, the New Hope Wesleyan Ultra Trail Run offers four trail distances at O'Bannon Woods State Park, featuring single-track forest trails, rocky sections, notable elevation changes, aid stations, timing, and awards for top f..

Two trail races, 50K and 25K, take place at Mammoth Cave National Park on October 24, 2026 starting from Bell's Tavern Pavilion. The crushed gravel out and back course has ascents and descents, cupless aid stations, and limited entries.

A community Turkey Trot in Wendell Moore Park offering a 5 mile run and a 4K walk with chip timing, finish medals, and awards including overall male and female prizes.

A Thanksgiving-themed chip-timed 5k at Turtle Run Winery in Corydon, IN, on November 7, 2026, featuring wine pours and event items including a t-shirt, collapsible wine glass, and a finisher medal that doubles as a wine stopper.

Trail races at General Butler State Resort Park on 11/07/2026 include 5K, 10K, 13.1 mile, 20K relay and a 6 Hours of Power loop event with park facilities and river overlook.

Trail endurance event at Deam Lake SRA featuring repeated laps of a 4.167 mile trail loop with 6 and 12 hour formats plus a one-lap fun run.

Deam Lake Winter Warrior is the Deam Lake stop in a winter series with 6-mile, 12-mile, 4-hour endurance and virtual options on the Yellow Trail. The event uses Buzzards Roost Shelter, is cupless, and has limited parking.

A *4 miles* trail run and walk at Veterans Park in Lexington on November 14, 2026, over mostly hard-packed dirt trails with grassy and short paved sections. The race is chip timed, offers awards, hydration stops, and a virtual option with m..

Trail ultramarathon weekend near Brownstown IN on Dec 5, 2026 with 10M, 50k, 100k and 100k relay, GPX files, live tracking, cabin packages and camping.

Experience an exclusive trail event at the Harry S. Frazier Scout Reservation featuring looping courses through Kentucky forest and a runner's village by John Barr Lake with distances from 5K up to 100 miles.

Trail races at Waverly Park in Louisville offering a 6.6-mile loop and a half marathon plus virtual options. The event is cupless, has an aid station about halfway, on-site restrooms, limited parking, and overall male and female awards.

Experience an endurance challenge at Elizabethtown Nature Park featuring an 8 hour race and a 5K trail run. Navigate a scenic loop of lakeside trails and rolling woodland terrain with full aid station support.

A point-to-point 50 Mile trail race along Indiana's Knobstone Trail with about 10,000 ft of elevation gain, organized by Trailblazer Running on April 10, 2027.

Timed ultraloop races and ruck events on a 5.4 mile loop in Parksville, Kentucky, with individual, relay, and ruck divisions. Full-service aid station, cup free policy, chip timing, and on site primitive camping.

Team based two hour 10K on the 575 acre Versailles farm with 18 checkpoints including biking, zipline, archery and canoeing; proceeds fund scholarships.