Heartbreak Hotel

“We drove 25 minutes out of our way to see a place called the Heartbreak Hotel, and Elvis never even stayed here?” he asked.

Well… yes. [1]I cannot begin to describe how much this place was in the middle of nowhere.

The famous 1956 Elvis song was inspired by a newspaper story about a man who left a suicide note that read, “I walk a lonely street.” Kenansville, Florida’s Heartbreak Hotel got its name in 1955, when a preacher named James W. Webb bought the decaying Piney Woods Inn, which some locals had started calling “the Heartbreak” because of its sad condition.[2]I think he was a landlord of mine at one point. Webb took the nickname and ran with it, even painting the hotel red. 

Never miss a post! Sign up here to get an email when we post something new! (Don’t worry: We’re talking one—maybe two—posts a week. And we’ll never share your address!):

It’s Not Easy Being Green

The hotel’s current owners painted it green, added shamrocks, and stenciled the words “Heartbreak” and “Hotel” in faux stained glass above its two front windows.

A Town Named for a Millionaire’s Wife

The original inn opened in 1915, when Kenansville was a cattle town on a railroad line. The Central Florida town more or less died when the railroad pulled out. (Kenansville, by the way, is named for Standard Oil multimillionaire Henry Flagler’s third wife. If you want to go down a rabbit hole about his scandalous divorce from Wife No. 2, and Wife No. 3’s likely murder by her next husband, this is a good place to start.)

A Lonely Street

Today, the town has just a few homes, a gas station with an attached restaurant, and a couple of historic buildings, including a charming little bank that sits right across what is now a lonely street in front of the Heartbreak Hotel.[3]Seriously, it’s nowhere near anything.

Featured Post: Cassadaga, Florida’s Kooky, Spooky Little Town

Please follow and like us:


Leave a comment