Several months ago, I was driving home from the Fort Lauderdale airport. It was late afternoon when I exited the turnpike and rolled into Florida City. The light at Palm Avenue flashed yellow and turned red. I stopped and stared out through the windshield. The sky out over the Everglades was beginning to soften and change colors.
The stoplight turned green, and I put the Jeep into gear. The road through Florida City is called South Dixie Highway. As you drive down it, between Palm Avenue and the Last Chance Saloon, the mainland begins to slip away and the Everglades takes over. The saloon appears on the right. On the left, just before you get there, is a turn lane. Take the left, and you’ll travel along the original path of the Overseas Highway.
Once upon a time, it was the only way to drive in and out of the Keys. Building the road, even agreeing to develop it, was a gradual process. The rumbles from island residents grew louder after Henry Flagler showed up. For many pioneer families who arrived in the county’s adolescence and continued to arrive in the early years of the 20th century, farming was a way of life. In the latter half of the 1800s, there was a time when the pineapple was king in the Florida Keys. Most of the pineapples shipped around the country were grown here.
It wasn’t just about pineapples but coconuts, tomatoes, melons, limes, onions and grapefruits. Before Flagler decided to build his railroad, all of that produce was shipped out of the Keys aboard boats. The islands were boat cultures. Life in the Keys relied on the water, not just for exporting goods but to bring mail, ice, coffee, sugar, friends, family, news and information.
The introduction of the Key West Extension of Henry Flagler’s Florida East Coast Railway transformed life along the island chain. His train moved its lifeline from the coastline and away from a reliance on ships, weather patterns and the successful navigation of the Straits of Florida. It was moved, for the most part, to the interior of the islands.
While the Over-Sea Railroad did not arrive in Key West until 1912, daily rail service was established between Miami and Knights Key in 1908. Knights Key is part of the collection of islands recognized as Marathon in the Middle Keys and is the last island crossed before driving over the Seven Mile Bridge. Twice a day, the train was rocking and rolling with a full head of steam up and down the Upper and Middle Keys.
It was also 1908 when farmers in the Upper Keys began voicing to the county their need for roads to help them adapt to the change. The packing houses boxing up the fruits of their labor for shipping were moving closer to the efficient new option offered by Flagler’s train. Local farmers needed better ways to reach them. While communities did what they could to pave some better way to transport their produce, it was not until 1917 that the county began responding to the need of better roads up and down the island chain. The county issued $100,000 in bonds to build roads on Key Largo and Big Pine, and a bridge linking Stock Island to Key West.
It was not just farmers asking for roads. The Miami Motor Club wanted to offer their members a “suburban” fishing ground in the Keys. In 1919, people lobbying on their behalf worked to allocate funds to develop roads and a bridge that linked the mainland to Key Largo. In 1922, $300,000 was set aside for roadwork in Key West, the Lower Keys and projects that benefited Upper Keys farmers, though not for a bridge between Key Largo and the mainland.
The big infrastructure investment came in 1926. Monroe County issued a $2.5 million bond for projects that connected (more or less) mainland Florida to Key West. Included in the budget was a wooden bridge connecting Key Largo to the mainland. On the Dade County side, commissioners agreed to finance 11 miles of road from Florida City to what became the Card Sound Bridge at Little Card Point.
Officially, the new conduit was called State Road 4A; it was also touted as the Overseas Highway. The celebrated grand opening was on Jan. 25, 1928. The highway looked nothing like it does today. In 1928, the road was incomplete and had a 40-mile gap between Lower Matecumbe and No Name keys that was bridged by automobile ferries. When the second version of the highway opened in 1938, the ferries were eliminated by a series of automobile bridges linking the Upper and Lower Keys.
It wasn’t until the third version of the Overseas Highway opened in 1944 that it began to resemble the road we drive along today. Should you choose to forgo the left turn near the Last Chance Saloon and continue straight, you will arrive at the 18-Mile Stretch. The top of the stretch, around MM 126, is still the South Dixie Highway. The green and white signs posted along the side of the road count down the miles it takes to reach the heart of Key West. Appropriately, they are called mile markers, and you have to pass more than a few of them before your tires start slapping the asphalt on the Overseas Highway.
It happens at about MM 115, at the county line, where Miami-Dade and the South Dixie Highway end and Monroe County and the Overseas Highway begin. Whichever version of the Overseas Highway you choose to take, the original or the modern route, you will come to a bridge leading to Key Largo, the automobile gateway to the Florida Keys. Welcome.
In 2025, I’ll be exploring the Overseas Highway, its history, attractions and points I find interesting.
