Trail Running calendar near Parksville 2026-2027

Run through the fields of Masterson Station Park in this cross country race featuring 5k and 10k distances. Enjoy a festive afterparty with bourbon tastings, music, and food trucks.

This charity 5K run and walk supports Talon Lopez, a 10-year-old with an anoxic brain injury. The event offers in-person and virtual options, plus a free run for kids 12 and under. It takes place at River Front Park in Brandenburg, Kentucky..

The Kentucky Cryptid Series - Wolfman is a trail run through Iroquois Park, offering 7-mile and 4-mile options. It's part of a four-race series where completing three earns a special survivor medal and shirt. This cupless event encourages p..

Experience a women only 5K obstacle mud run at Pop's Landing at Haddix Farms. Join a community focused on unity and empowerment while tackling a fun mud course to support breast cancer awareness.

Run for 12 hours on a scenic loop course through Saunder Springs Nature Preserve. Choose to tackle the trails solo or as part of a two or four-person team. The challenge is to cover as much distance as possible on terrain featuring forests,..

Experience a cross country race through the scenic grounds of Talon Winery in Lexington. Enjoy a finisher award plus a glass of wine and live music at the post race celebration.

Experience a unique trail race through the historic Blackacre Nature Preserve featuring wooded paths and farm animal sightings. Choose between 4 or 8 mile distances and enjoy post race ice cream at the historic homestead.

Join the 30th annual Spoonbread Festival 5K in historic Berea. Run or walk a flat, paved course on the city trail, with festivities supporting the local chamber of commerce. Enjoy chip timing, a race shirt, and the vibrant atmosphere of the..

Run, walk, or volunteer at the Run Baby Run 5K to support NICU babies. This flat course on Lexington's scenic Legacy Trail includes a kids' dash and virtual options. All proceeds purchase supplies for families in neonatal intensive care uni..

Experience the natural beauty of the Big South Fork National River and Recreation Area with a loop trail race featuring 17.5 mile and 10K options primarily on single track terrain.

Experience the natural beauty of Lexington at the Raven 10K Trail Run. Run or walk through grassy fields and primitive trails at the Raven Run Nature Sanctuary or join the event virtually from any location.

Experience a scenic trail run through the Red River Gorge on a private looping course. This cup less half marathon supports local search and rescue teams while offering a festive atmosphere with medals and post race meals.

Run through the scenic trails of Jefferson Memorial Forest in this cupless trail event featuring 5 mile and 8 mile distances. Earn special series awards while exploring the beautiful Horine Reservation landscape.

Experience a unique trail run through the hills and woodlands of Gravel Switch. Enjoy a route featuring meadows and steep climbs followed by a pancake breakfast and handmade awards at the local heritage festival.

The Little Rooster Run offers a weekend of trail events in Glencoe, Kentucky, from a kids' fun run to a 5K and the unique Mini Barnyard Ultra. This "last runner standing" format challenges participants on a 2-mile loop every half hour. Proc..

Join the second annual Running Pumpkin 5K in Lexington's Coldstream Park. This fall event supports Gleaning Housing, a local nonprofit building affordable rental homes. Participants are welcome to bring a pumpkin or wear a costume, with sna..

Celebrate Thanksgiving at Pulaski Park with a scenic trail run overlooking Lake Cumberland. Choose between a 5K or a Fun Run while supporting the American Cancer Society and enjoying views of the water.

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 from December 13 to December 27, 2026 offering 6.5 Mile and Half Marathon distances plus virtual options. Part of a Winter Warrior Series with course markings, on-course aid, awards, and a series medal for multip..

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.