At various points during the 19th century, gentlemen from Tennessee would travel to the north - to property just across the Kentucky border­­­ - to settle their differences in a pistol duel. At that time, dueling to resolve arguments or conflicts was illegal in Tennessee, but was a lawful activity in Kentucky. According to historical accounts, famous figures such as Andrew Jackson and Sam Houston were said to have visited the "dueling grounds" site as witnesses to such duels.

When dueling was no longer legal in Kentucky, the 260-acre "dueling grounds" had more conventional agricultural uses until a group of investors acquired the property in the 1980s to develop a unique "turf only" race track to host Steeplechase races.

That vision came to life when a 1 and 5/16 mile race course and a colonial-style clubhouse opened for business on April 22, 1990. The race track was named Dueling Grounds in recognition of the colorful history associated with the property.

The race track operated as Dueling Grounds until 1998, when new owners renamed the track Kentucky Downs. In 2007, a group of investors led by Nashville businessman Ray Reid and former Lone Star Park president Corey Johnsen purchased a majority interest in Kentucky Downs with a vision for expanding the scope of its operations in the future.

Today, Kentucky Downs conducts its live turf racing meet each September on the only "European-style" race course in North America. The meet is staged in an informal festival setting and features the annual running of the Grade III Kentucky Turf Cup race. Additionally, Kentucky Downs offers year-round simulcasting, serves as the site for numerous special and entertainment events and hosts charity Bingo for a number of community-based organizations in Franklin and Simpson County.

And in 2011, Kentucky Downs added Historical Horse Racing to its "menu" as the next step in the transformation of what was once the site of "pistols at dawn" to a year-round entertainment destination.