KEYS HISTORY: BRIDGE CONSTRUCTION CONNECTED A SERIES OF ISLANDS

Channel 5 Bridge after it was transformed into an automobile bridge. SCOTT DeWOLFE COLLECTION, FLORIDA KEYS HISTORY CENTER/Monroe County Library

When the first version of the Overseas Highway opened in 1928, it stopped at the end of Lower Matecumbe Key. It didn’t stop for good but for 40 miles or so. 

It picked up again at No Name Key and, from there, traveled the rest of the way to Key West – though not along the same path as it does today.

Automobile ferries were used to bridge the gap between the Upper and Lower Keys. Two ferries were in operation and departed the terminals daily at 8 a.m. and 1 p.m. However, the ferry system was not the most reliable mode of transportation as it was challenging to stick to a business schedule while navigating the ebb and flow of the tides, weather and all the things that go wrong with boats.

The plan to eliminate the ferry system was to build a series of automobile bridges between Lower Matecumbe Key and Big Pine Key that would have roughly paralleled Flagler’s railroad bridges. The first workers for the bridge projects began arriving in November 1934. Most of them were World War I veterans who were brought in and housed in three work camps, one on Windley Key and two on Lower Matecumbe Key.

The first task at hand was to build a bridge connecting Lower Matecumbe to the next island in the chain, Jewfish Bush Key. Today, that island is called Fiesta Key. The work halted on Sept. 2, 1935, when a Category 5 hurricane devastated the area and took hundreds of lives, many of them those veterans. Remembered as the Labor Day Hurricane, it still registers as the most powerful storm to make a North American landfall.

Driving away from Lower Matecumbe in the direction of Key West, the remains of two of the veteran’s projects are still visible. One is more concrete than the other.

Back in 1935, before the storm, there were dredges out in the water scooping the bottom from one area and dumping it into another until a stretch of land began to appear. On that land, a causeway was to be built that reached out from the edge of Lower Matecumbe to what would have been the first new automobile bridge in the chain. (Today, driving from Lower Matecumbe Key to the Channel 2 Bridge is across the fill, too.)

The remnants of the 1935 causeway have since become hidden in plain sight. Left to its own devices, the fill was slowly taken over by trees until it became disguised as an island. Driving between Lower Matecumbe and the bridge, it is there on the right. The manufactured island was named Veterans Key to honor the men who worked to build it, many of whom perished in that horrible hurricane.

Between Veterans Key and the modern Channel 2 Bridge, out in the shallows of Florida Bay, are eight bridge piers that have been haunting the shallows ever since. Had the hurricane not struck and the job been completed, the piers would have supported the bridge linking Lower Matecumbe to Fiesta Key. Once or twice, people have asked if some of the veterans were buried in them because that is a story that is occasionally passed around. Of course they weren’t, though locals often refer to them as the Coffins, which they represent in a metaphorical sense.

The first bridge after Lower Matecumbe is the Channel 2 Bridge. There are two Channel 2 bridges. The modern one was built in 1981. The former bridge, originally a railroad bridge, can be seen on the bayside. Usually, there are people standing on it and fishing. 

When Henry Flagler traveled in his private railcar between the mainland and Key West on Jan. 22, 1912, the Channel 2 Bridge wasn’t finished. Because of Flagler’s failing health, there was a push to finish enough of the railroad for the train to make the trip. In 1912, at Channel 2, Flagler crossed a temporary wooden trestle bridge. The railroad viaduct from which people fish today was not operational until 1913. The entire railroad project wasn’t officially completed until 1916. Henry Flagler passed away at the age of 83, on May 20, 1913.

After driving over the Channel 2 Bridge, the highway crosses more railroad fill that has since become known as Craig Key. In the early 1930s, Roland Craig, a Miami-based charter fishing captain, leased the stretch of roughly J-shaped railroad fill from the Florida East Coast Railway and established Camp Panama. That camp grew into the town site of Craig, named for Roland. In addition to a hotel, gas station and docks, a post office was established. Craig survived the 1935 Labor Day Hurricane by clinging for dear life to the railroad tracks.

The small town of Craig moved on after Hurricane Donna, a destructive Category 4 hurricane, blew through the Keys in 1960. It was the most powerful storm to strike the Keys since 1935. The post office was moved to Layton, a small community on nearby Long Key. Before arriving at Long Key and passing through Layton, there is the modern, high-arching Channel 5 Bridge that was built in 1982. Like the Channel 2 Bridge, when Flagler rocked and rolled across Channel 5, the railroad tracks traveled over a temporary wooden trestle bridge.

People like to ask about Channels 1, 3, and 4. Because there are Channels 2 and 5, the others

should be around, too, right? I have never come across an answer to the question. A similar question arises when talking about the work camps created to house the World War I veterans. Three of them were created, one on Windley Key and two on Lower Matecumbe Key. Camp 1 was on Windley Key. Camps 3 and 5 were on Lower Matecumbe. For whatever reason, Camps 2 and 4 were located in Florida, but in St. Petersburg and Clearwater. 

As for the highway, before we get to Long Key, there is still more railroad fill to cross.

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.