Kenansville: Henry Flagler's Divorce

by Mike Miller
(Mount Dora, Florida)

Heartbreak Hotel

Heartbreak Hotel

Kenansville is a spot on US-441 about halfway between Yeehaw Junction and Holopaw. Most travelers whiz through without knowing anything about the history of the place. It's name ties into the history of one of Florida's iconic developers, Henry Morrison Flagler.


Henry is the man who really opened up Florida to tourism. After making a fortune as John D. Rockefeller's partner in Standard Oil, he retired and focused his business skills on ventures in the Sunshine State. His projects and invested capital in the 1880's through 1912 transformed Florida forever.

He started with big hotels in St. Augustine, bought a railroad, and then extended his railroad and hotel empire down the east coast of Florida until he finally made it all the way to Key West. The Overseas Highway follows the roadbed of Flagler's Florida East Coast Railway.

Flagler's first wife had died, and his second wife had been institutionalized for mental illness for many years. You might say he had been unlucky in love. At last, however, he fell in love with a lovely young lady named Mary Lily Kenan, and wanted to marry her.

In those days, it was almost impossible to get a divorce in Florida. Flagler convinced the Florida Legislature to pass a bill allowing a spouse to get a divorce if their mate was mentally ill. It was considered a scandal at the time, but Henry Flagler got divorced. He and Mary Lily got married and lived happily ever after in Whitehall, their Palm Beach mansion.

One of Flagler's railroad spurs headed south close to the route of what is now US-441. One of the little communities along the way offered to name the town after him if he ran the railroad through it. Flagler declined the name offer, but asked them to name it after his wife instead. And thus was born Kenansville.

Most Floridians know the town as the home of the Heartbreak Hotel. Rumor has it that Elvis stayed there and named his song after the place. The truth is the owner of the hotel liked the song and named his hotel after it.

The picture above is of Heartbreak Hotel in 2003. I believe one can still rent a nice clean room there and be surrounded by the quiet of the old Florida prairie.

Comments for Kenansville: Henry Flagler's Divorce

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Mar 27, 2017
Cow Palace
by: Anonymous

My hunting companions and I would eat dinner regularly at the Cow Palace and drink Heineken beers for $2 a piece. We would call ahead during the week just to make sure they stocked up so they wouldn't run out. Best Steaks east of Bern's. Fond memories.

Jun 14, 2016
Kebabs like School
by: Anonymous

I was lucky enough to have gone to school while it was still open. I have nothing but fond memories and had the best Teachers (:

Jun 14, 2016
Childhood memories
by: Michelle Little (Campbell)

I remember passing this place everyday to go to school in St.Cloud from Yeehaw. There was a man named Mr.Webb that wrote a book many years ago and he has written about this place as well. He was crippled but had a van customized that he could drive and he would pick us up and take us to church. I have a lot of family buried in Kenansville as well. Thanks for the article!

Jun 14, 2016
The Sale
by: K Marquette

Passed by there just last week, June 2016 and the building and land is for sale. Looks like it would be a nice B&B with some great fishing on the lakes that are around that area.

Nov 01, 2015
The view out my window.
by: Marla Hughes

That picture basically mirrors the view out my side windows. I grew up across the street and down a lot from the Heartbreak. It's had it's ups and downs through the years, as has Kenansville.
Thanks for the nicely done article. :-)

FLORIDA BACKROADS TRAVEL SAYS

Thanks for the kind words, Marla. You probably know how rare a person you are: someone who grew up in Kenansville, Florida. Not many people in the world can say that.

Sep 07, 2014
Hotel is for sale
by: Anonymous

The building has been For Sale for several years and recently the gift shop has closed.

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