KEYS HISTORY: THESE ISLANDS PRESENT SOME NAMING MYSTERIES

a black and white photo of an airplane wing

Conch is more than a five-letter word in the Florida Keys. It is a marine gastropod, a musical horn, a treasured souvenir, a culture and the symbol emblazoned on the national flag of the Conch Republic. 

It’s not surprising that at least one of the islands making up the archipelago would be called Conch Key. 

There are two of them, Conch Key and Little Conch Key; they have different stories to tell. Though the name’s origin is unclear, it dates back to at least 1849 when Gerdes wrote in his “Reconnaissance of the Florida Reef and all the Keys”: “The first islands between Duck Key and Long Island are named the Conch Keys.” On some of the old charts, Long Key is called Long Island. As a side note, there are maps that identify Plantation Key as Long Island, too.

Rolling over the Long Key Bridge as it parallels the old Long Key Viaduct, Henry Flagler’s favorite of the railroad bridges (people love to fish off the old bridge), is Conch Key. It is the larger of the two Conch Keys and is home to a close-knit, and tightly-packed, residential community.

The island does not look like it did when Flagler’s men dredged up the railroad fill. Since those days, it has put on a little weight. The original Conch Key existed only on the Gulf of Mexico side of the highway. The part of the island that has since spilled over to the other side of the highway, the Atlantic side, is the result of some hearty dredge work back in the 1950s.

As the highway rolls on, it connects Conch Key to Little Conch Key atop the work done by the men who built the Key West Extension of the East Coast Railway. When they were done, a line of railroad fill, topped with ties and rails, allowed a mighty steam locomotive to roar and whistle between the two islands. While historically known as Little Conch Key, it was called Walker’s Island in the 1930s, and used as a family fishing camp. One of the families was named Walker. It has remained a privately owned island and, while not much of it is visible while driving past, for those looking to escape to a private island for a few days it offers a handful of vacation rentals and a little slice of secluded island paradise.   

Passing over more railroad fill and the bridge across Tom’s Harbor Cut, the road travels past a resort island on the left called Duck Key. There is more to say about Tom, and we will get back to his story on the other side of Duck Key, where the subject makes more sense. In the meantime, at MM 61, Duck Key was only connected to the highway by a short causeway and bridge in the early 1950s.

As is typically the case, Duck was not the first name attached to the island. One of its early Spanish names was Chinche. Also, one of the slang Spanish words for bed bugs is chinche. Thankfully for future visitors to the island, Chinche was not the last name given to it. In 1772, it was labeled Reynolds Island. George Gauld noted it as Duck Key in 1775. 

In 1828, J.W. Norie wrote: “Duck Key, some two miles long, low, rocky, & covered with mangroves; some small patches of good land with a little timber. This island formerly held saltworks, but they were transferred latterly to Key West, owned by Mr. Howe, who is also possessor of this Key.” 

I cannot state why the island was called Duck Key with any degree of absolute certainty. However, if you go back to a time before the canals were dredged and the big resort and the homes were built, it is easier to see that the island is shaped a bit like a duck’s head.

Leaving Duck Key in the rearview mirror, Tom and the islands, cut, harbor and bridges named in his honor come back into the picture. Obviously, he is a big name along this little section of the road; the really big question is, who was he? I don’t have a satisfactory answer to what is an excellent question. However, documents make it clear that his name has been around since the 1800s.

One early account referencing his name was published in the Jan. 19, 1858, edition of the Charleston Daily Courier: “…chartered a beautiful little yacht schooner, called the Foary [spelling might be off because the newspaper print is blurry], and we having added to the stores, as well as a first-rate cook and steward, sailed to visit the Keys we were interested in, on the morning of the 12th of December. … Next day we sailed down between the Reef and the front of our Islands, as far as Thomas’ Harbor…”

While one aspect of the name has been debated, another has not. The names used to identify these markers have fluctuated between Thomas and Tom. No matter the version of the name, what has always been true is that it has been possessive. In an 1849 pamphlet about sailing directions in the Keys, “The island W. of Duck Key is Tom’s Island.” The name Thomas’ Harbor Keys was used in an 1855 document.

Whoever Thomas or Tom was, his name has stuck around and is now used to identify the two islands on the Atlantic side of the highway that become visible after passing Duck Key. It is also used to identify the harbor and Tom’s Harbor Bridge. Straight ahead is Grassy Key. When we get there, the island will offer an introduction to, among other interesting tidbits, the birth of the movie and television star Flipper.

In 2025, I’ll be exploring the Overseas Highway, its history, attractions, and points I find interesting.  

Brad Bertelli
Brad Bertelli is an author, speaker, Florida Keys historian, and Honorary Conch who has been writing about the local history for two decades. Brad has called the Florida Keys home since 2001. He is the author of eight books, including The Florida Keys Skunk Ape Files, a book of historical fiction that blends two of his favorite subjects, the local history and Florida’s Bigfoot, the Skunk Ape. His latest book, Florida Keys History with Brad Bertelli, Volume 1, shares fascinating glimpses into the rich and sometimes surprising histories of the Florida Keys. To satisfy your daily history fix, join his Facebook group Florida Keys History with Brad Bertelli.