The Ultimate Kentucky Road Trip Playlist

    Taking a trip through Bluegrass Country? This playlist will have you loving the hills and hollers of Kentucky…

    Ok, so obviously, this playlist is a little on the country side… How could it not be? Like all our state-specific playlists, we have a mix of both songs from Kentucky natives and songs featuring Kentucky or Kentucky towns and cities to make the ultimate Kentucky road trip playlist. Here are a few of our favorites from the list:

    Paradise – John Prine

    If there’s a song that makes a body long for a country home more than John Prine’s Paradise, we haven’t heard it. His folksy voice coupled with the picture he paints of Kentucky make it perfect for anyone making a homecoming to Kentucky or just passing through. In fact, we argue you could just listen to this song on repeat for the whole road trip and be perfectly happy. (The version above features Johnny Cash, Vince Gill, Marty Stuart, and a very young John Prine. It’s fantastic.)

    My Old Kentucky Home – Johnny Cash

    He may have been born in Arkansas, but Johnny Cash’s My Old Kentucky Home would make you think otherwise. It’s a simple little toe-tappin’ song with a country flavor for your drive through the backroads of Kentucky.

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    Kentucky Gambler – Merle Haggard (and Dolly Parton)

    A cautionary tale to say the least, this song will give you a few reasons not to bail on your Kentucky hometown in favor of the casinos. So just keep in mind, if your road trip is actually more of a “leaving your family and gambling away all your money,” you should probably turn around.

    Kentucky Woman – Neil Diamond

    Perfect for rocking with the windows down, Neil Diamond makes any man want to take a road trip through Kentucky. Without a doubt, it’s the anthem of every female in the state.

    Kentucky Rain – Elvis Presley

    You can only hope and pray a thunderstorm rolls in during your road trip. Singing this song while the storm clouds start to release a rain shower sounds like a pretty epic day on the road.

    Blue Moon of Kentucky – Bill Monroe

    When it comes to bluegrass, it doesn’t get much better than Bill Monroe. When it comes to classic bluegrass songs, his Blue Moon of Kentucky also reigns pretty supreme. It would be downright criminal and insulting to the fine folks of Bluegrass country to not include this song. Oh, by the way, this was also Elvis’s first recorded song. (Monroe wrote it way back in the 1940s)

    Kentucky – The Everly Brothers (and Billie Joe Armstrong & Norah Jones)

    The Everly Brothers are legendary and their smooth voice lends itself perfectly to this homage to their home. We also threw the Billie Joe Armstrong/Norah Jones version from their Everly Brothers tribute album. Of course, the Kentucky natives also show up on the playlist with some of their other hits and Bowling Green, an ode to their beloved Kentucky hometown.

    Coal Miner’s Daughter – Loretta Lynn

    Capturing her home like only Loretta can, Coal Miner’s Daughter was a big hit for her but also paints the story of Appalachian life in a way even us Yankees can understand.

    The rest of the playlist features other Kentucky greats like Dwight Yoakam, Montgomery Gentry, the Kentucky Headhunters, and more.

    Click here to grab the playlist on Spotify.


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