One thing I love about my Facebook group “Florida Keys History with Brad Bertelli” is the comments. The group has attracted thousands of members, many of whom would be considered “old-timers” who were either born in the Keys or moved here as children. 

The group allows me to share my knowledge of Monroe County and the Keys and an amazing array of images (thanks mostly to the Key West Library’s Florida Keys History Center).

I started the group in December 2021 as an outlet where I could share a taste of the local history every morning. The response has been overwhelming, and it has blossomed into a group that inspires the exchange of memories, insights and stories of the old days told by those who lived through them. I love it because everyone in the group learns new and fascinating tidbits of history about the Florida Keys — myself included. 

Because of the group, and my role as a local historian, I receive many history questions through social media, emails, texts and phone calls, and I try to respond to all of them. Sometimes I have the answers at the tip of my fingers, and sometimes I need to phone a friend or dig into some research, and sometimes time gets away from me, and I forget to follow through, which is why I like to tell people that if they don’t hear back from me in a week or two to reach back out. 

Every query affords me the opportunity to learn more about this island chain. While I have acquired a pretty solid foundation of knowledge and will continue to learn about the Keys, there is just way too much out there for anyone to know everything. While I consider my specialties to include Indian Key (once upon a time the most important island in the Keys not named Key West) and Black Caesar (the legendary pirate of the Keys), one of the areas of local history I like to play around with is how the islands, communities and their roads came upon their names.

Some of the names have more obvious origin stories than others. For instance, Bahia Honda is the Spanish phrase for deep bay, and the island does boast one of the island chain’s deepest bays. Because of the island’s bahia honda, its iconic bridge was the most challenging of Henry Flagler’s railroad bridges to build. 

Key Largo is another obvious choice as the island’s early Spanish name was Cayo Largo, which is fitting as largo means long, and Key Largo is the longest and largest of all the Keys. On the other hand, Crawl Key, in the Middle Keys, was named for a less apparent reason. Back in the days when the local waters were still filled with turtles and people fishing commercially for them, the island was home to turtle crawls where their catch could be corralled before being brought to market.

For those driving up and down the Overseas Highway, one of Crawl Key’s significant features is a road sign identifying Banana Boulevard. Every time I drive between Grassy Key and Curry Hammock State Park and see the Banana Boulevard sign, I smile and don’t know why. I just do. There are scores of other unusually named roads on the islands. However, one of the wildest names and a personal favorite is a narrow road on Key Largo near MM 103 called Transylvania Avenue.

Recently, someone from my group asked if I knew how Transylvania Avenue got its name. The strikingly different identifier is found in an Oceanside community filled with obvious sub-tropical island names like Jewfish Avenue, Snapper Avenue, Kingfish Street and Blue Runner Street. Why the weird name? I will posit three theories addressing the more obvious connotations. Likely, all of them are wildly off base.

First, the person who decided on the name had a familial connection to Romania, Transylvania’s home. Second, they graduated from Transylvania University, which, interestingly enough, is located in Lexington, Kentucky. Transy, as the university is known, is home to the Pioneers. The symbol on their baseball caps is a flying bat, and the university’s podcast is “Flying with the Pioneers.” I’m not sure about the connection between pioneers and bats, but the connection between the little flying mammals and Transylvania is crystal clear.

Of course, there is always the possibility that the avenue was named by a fan of Bram Stoker’s 1897 novel “Dracula,” whose castle was located in Transylvania. The third reason is probably a reach, but is worth noting because there is a kernel of truth in it, whether it was intentional or not. 

The rough translation of transylvania is “other side of the woods.” At MM 103, where the avenue is located, a hammock (or woods) separates two residential neighborhoods. The hammock is bordered on one side by Transylvania Avenue, so, technically, it is the first road on the other side of the woods.

Somewhere out there is also what is probably the real reason why that road was given that particular name, and I hope it turns out to be a story with a bit of flair because a choice like that deserves an origin story with a little razzle-dazzle.

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.