KEYS HISTORY: RAILWAY PAVES WAY FOR A DRIVE ON THE STRETCH

a black and white photo of a train track
Freshwater pumping station at Manatee Creek. JERRY WILKINSON COLLECTION/Contributed

When driving in and out of the Florida Keys, most people take the 18-Mile Stretch. It is usually the fastest route. Card Sound Road is the other option. It offers a classic dive bar with historically amazing conch fritters, but it takes a little longer. 

While the Stretch does not have a Panther Crossing road sign or Alabama Jack’s waiting on the side of the road, it does have a few stories to tell. 

For starters, the 18-Mile Stretch follows the original right-of-way of the Key West Extension of Henry Flagler’s East Coast Railway. William J. Krome, an engineer working for Flagler, plotted it and the rest of the railway line to its Key West terminus. Homestead’s Krome Avenue is named for him.

Much of the stretch was created with fill scooped out from under the water and piled up until a long stretch of land was created. It started in the spring of 1905 when 11 dredging barges left Miami for work sites throughout the Keys. Four were assigned to Key Largo, where two barges dredged their way south from the mainland, and two dredged north from Jewfish Creek until enough fill was created to support a railroad right-of-way connecting the mainland to Jewfish Creek.

One of the challenges of constructing the line was an adequate fresh water supply. It took a lot of water to quench the thirst of both the workers and the machinery that released all of that steam every day – about 5 million gallons per month. Three primary fresh water sources were used to satisfy the needs of the railroad. One was discovered at Manatee Creek. Initially identified as an entry point for dredges working to create fill on the east side of the right-of-way, it was only after survey teams arrived that they discovered the creek had fresh water. The two other primary fresh water sources were at Homestead and Big Pine Key.

Manatee Creek appears around MM 115; it is in the general area where the road crosses the county line, stops being the South Dixie Highway and becomes the Overseas Highway. During the construction years, there was a pumping station sucking water out of the creek and filling cypress holding tanks rolled atop flatbed rail cars. 

While tremendous effort was put into creating the Key West Extension, the Over-Sea Railroad was a relatively short-lived endeavor. Henry Flagler rolled into Key West on his private railcar for the first time on Jan. 22, 1912. Twenty-three years later, on Sept. 2, 1935, a Category 5 hurricane that still registers as the most powerful storm to make a North American landfall crashed over the Keys.

Not only did the hurricane take hundreds of lives, it destroyed 40 miles of railroad tracks and placed a period at the end of the run of Flagler’s train. The railroad right-of-way was sold to the state for $640,000. When the third version of the Overseas Highway opened in 1944 (the first two versions followed what is now Card Sound Road), the 18-Mile Stretch was incorporated into the route to shorten the drive into the Keys. 

When I first started driving in and out of the Keys, the Stretch didn’t have fences or a concrete median separating the southbound and northbound lanes. In those days, marsh rabbits were still nibbling tender grasses at the road’s edge. Sometimes, too, alligators and crocodiles occasionally crossed or didn’t quite make it and were run over time and time again until they looked like leather.

Once, when I was driving out of the Keys, at about MM 122, I saw a baby crocodilian in the middle of the road. Its pointed head was held up high, and its little jaws were wide open in a defensive stance; cars whistled past, one after another. I watched in the rearview mirror as it snapped its jaws and slowly faded from view.

I hate that I didn’t stop. On my way back to the Keys, I scanned the road but found no sign of it, squashed or alive. I don’t know if it was an alligator or a crocodile; it could have been either. South Florida and the Keys are the only places where that hesitation can be made. One thing that makes this bottleneck special is that it is the only place in the world where the two species co-exist.

I haven’t seen a marsh rabbit, crocodilian or even a carcass in more than a decade, not on the road. Sometimes, at the top of the stretch, where the road rises a bit, and you can see down into the Everglades, I’ll see the dark outline of an alligator out in the grassy shallows. Back in 2023, I saw on the news that a 10-foot gator crawled out onto the Stretch and caused a traffic jam. 

However, you will pass a golden-yellow road sign declaring Crocodile Crossing. Also, there is Lake Surprise. The body of water was given its name because finding it was unexpected. It appears on the Key Largo side of the Jewfish Creek Bridge. In his diary, Krome wrote about the lake: “This body of water which we call Lake Surprise is nearly 2 miles long by 1 mi wide and from 6’ to 8’ deep with rock bottom. It is entered from both Blackwater Sound and Barnes Sound by obscure hidden creeks and is not shown on any map or chart. We had no idea of its existence and it has played (indecipherable) with all my calculations.”

From there, it is about 104 miles to the Cow Key Channel Bridge and Key West.

There is a lot to talk about before we get there.

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.