CONTACT US  |  email icon

The best source for everything Deep South USA


Kentucky Fly Drives and Trails

Country Music Highway

Fire up a Ricky Skaggs tune and your car’s engine and hit this winding ribbon of mountain road for a one-of-a-kind Kentucky adventure. Highway 23, the ‘Country Music Highway’, is 144 miles along the state’s eastern part. It stretches from Greenup County in the north to Letcher County in the south. This National Scenic Byway provides an introduction to many musical legends who have emerged from these ancient Appalachian hills and hollows, such as Skaggs, Patty Loveless, The Judds, Billy Ray Cyrus, Crystal Gayle, Hylo Brown, Gary Stewart, Rebecca Lynn Howard, Dwight Yoakam and many more.

You should allow two days for a leisurely drive, which connects the towns of Greenup and Whitesburg. At the midway point, near Paintsville, you will find legendary Butcher Hollow, where a dusty gravel road leads to the humble log cabin in which the Queen of Country Music, America’s beloved ‘Coal Miner’s Daughter’, Loretta Lynn, was born on April 14, 1935. Today, her brother, Herman Webb, still gives tours of the family home.

In Prestonsburg, visit the Mountain Arts Centre, a performance hall home to the Kentucky Opry, a musical variety show modelled on the one in Nashville, Tennessee.


What to do

  • Family Fun in Deep South USA


    From the great outdoors, to fantastic shows and parks...
    Artists performing at Grand Ole Opry


    For American music, all roads lead to the Deep South...
    History of Deep South USA


    Travelling through the Deep South is a history lesson in itself!
  • Deep South USA Cuisine


    Sample a taste of the real Deep South…
    Heritage of Deep South USA


    Discover our colourful cultural beginnings…
    Man playing gold in Deep South USA


    Perfect your Southern swing in stunning settings…


Alabama Tourism Logo  Kentucky Tourism  Louisiana Tourism  Visit Mississippi Tourism Tennessee Tourism

Ask an expert who's been to Kentucky

Start planning your Deep South USA road trip by contacting one of our Southern specialists.