Florida 500: The Tamiami Trail



A Tangential History of the Tamiami Trail


By Ross Hancock


Kartik’s recent series on the history of the Florida Turnpike got me thinking about a road project from an earlier time that also had a great impact on the state. On so many beautiful days like today, I have crossed the peninsula via the Tamiami Trail to paddle in my favorite places — the “Shadow Country” backcountry rivers and bays of the Ten Thousand Islands.

There is so much Florida history in the Lostman’s River country south of Chokoloskee, much of it told in Peter Matthiessen’s trilogy that incorporates the Killing Mr. Watson novel. The Tamiami Trail itself takes me past mile markers of Florida history, from its eastern terminus on Brickell Avenue, down Little Havana’s Calle Ocho, past Miccosukee villages and their casino, the ValuJet Flight 592 crash site memorial, tourist traps like Safari Park and the Swamp Ape Research Center, the abandoned Everglades Jetport, and America’s tiniest post office. Near the Miami-Dade/Collier border, the otherwise laser-straight Trail takes a mysterious jog north, called the “Forty-Mile Bend.”

Ironically, the road itself threatens my fragile destination. But that is another story.

By 1911, various Florida counties were issuing bonds to build hard-surfaced roads to accommodate the hundreds of automobiles in the state’s larger cities. Inter-city car travel had been made imaginable by a 1909 auto endurance race between Tampa and Jacksonville. The race took four days. There was statewide enthusiasm for road projects to bring winter tourists down the east and west coasts.

Boosters from Florida attended the Dixie Highway Association convention in Chattanooga in 1915, lobbying to extend Dixie Highway through central Florida. Though their persuasion failed, the Florida delegates quickly reassembled in Orlando as the newly formed Florida Highway Association, and backed several projects, including a road from Tampa to Miami. That same year, the state legislature created the Florida State Road Department, and in 1916, Congress passed the Bankhead Act to provide federal highway aid to a car-crazy nation.

Sections at each end of the Tamiami Trail were gradually patched together, including, by 1918, 35 miles from Brickell nearly to Dade County’s western boundary. But the real challenge would be completing work on the final cross-state segment from Naples to Dade, which crawled along at one-and-a-quarter miles per month, despite having a steam-powered “walking dredge” and an average of 150 men working at any given time. The Tamiami Trail would take 13 years, two-and-a-half million dynamite sticks, and $8 million before opening to traffic. Workers would drown and be crushed in accidents. A world war, a land bust, and a devastating hurricane would be endured first.

It would take an encyclopedia to tell the story of the Trail and the politics and technical challenges involved. I will tell a slice of a chapter of it, starting with my perspective at water level, in a handmade kayak in Mr. Watson’s shadow country.

We are in a mangrove creek at the entrance to Sweetwater Bay, a 15-mile paddle south out of Chokoloskee. The Everglades once fed pure water into the foliage bordering this quiet bay, and pirates replenished their water stores here. The flow comes from Sweetwater Strand, and while the sheet flow is a trickle and the water is tainted by agricultural runoff, the strand is home to otters that feast on oysters as far north as the Tamiami Trail, just a few miles inland. It is not unusual to see sawfish and porpoises hunting in the shallows here.

An osprey overhead watches flamingo-colored spoonbills work the mud flats. The Park Service has provided a wooden platform for camping. If you tie up to it on a moonless night, you can see the Andromeda Galaxy above, and the whole Milky Way is reflected in the water below along with bioluminescent fireworks in the wake of shrimp and trout.

The creek behind us leads to Chevelier Bay, named after a French poacher who lived on it a hundred years ago. Jean Chevelier used his cabin as a base to shoot tropical birds for European collectors, and to dig for gold among the 2,000-year-old Calusa mounds in the area. Chevelier’s friend Edgar Watson lived just downriver toward the Gulf until he was gunned down by his neighbors in 1910. Mr. Watson virtually invented sugar farming in Florida, which is yet another history story for another day.

It was on pristine Chevelier Bay, Sweetwater Bay, and 200,000 acres of precious wilderness extending all the way east to the Dade County line that Capt. J.F. Jaudon, an ambitious developer who served as Dade’s tax assessor, wished to erect the city of Chevelier, along with development of sugar and rubber farming, logging, oil drilling, and the distillation of rum. For that dream to be fulfilled, the Tamiami Trail would have to be completed.

By 1921, Lee County, which bordered Dade at the time, was not making progress extending the Trail from Naples toward Miami. Capt. Jaudon took matters in his own hands and started working westward from the Dade side, extending the road for 16 miles through property he owned. This stretch comprises most of what is now the unpaved Loop Road from the east end of the Forty Mile Bend toward Monroe Station.

Jaudon also built his first development on that road, called Pinecrest, which he marketed as “The Next Miami.” While Jaudon was engaged in that project, Southwest Florida advertising magnate Barron Collier obtained state approval to complete the Tamiami Trail from the west, rerouting it through his own land to circumvent his rival’s landholdings.

In appreciation for taking over work on the Trail, which was finally opened in 1928, the state named a new county for Collier. Bypassed by the highway, Jaudon’s development plans were dashed until gangster Al Capone financed a hunting lodge, casino, and airstrip in Pinecrest, where he could do business with minimal scrutiny. The remote community survived the depression, but the burning, possibly by arson, of Capone’s Pinecrest Lodge in the mid 1930s and the depletion of logging in the area turned Pinecrest into a ghost town by the early 1940s.

Today the Forty Mile Bend of the Tamiami Trail, 40 miles west of Miami, looks like bad surveying, as if the eastbound and westbound crews almost missed each other. But it is really just a monument to the competing ambitions of Collier and Jaudon.

Where the road bends back from northwest to due west, if you turn onto the unpaved Loop Road at Monroe Station and drive south a few miles, you will come to a small bridge over a creek of Sweetwater Strand. This is a cypress-shaded spot immortalized in Clyde Butcher photos, one of the prettiest spots on the planet. You can observe the otters and alligators and wood storks, and watch the water flow Gulfward toward Sweetwater Bay, Chevelier Bay, and Lostman’s River — all now under protection of the National Park system — safe from poachers and developers, but thirsty for water that is unblocked by roads and untainted by runoff.


This arch stood over the Tamiami Trail at the Dade-Collier line until it was demolished in 1958 when the road was widened.



Ross Hancock (www.voterosshancock.com) was the 2012 Democratic nominee for State House District 114. He is currently a candidate for Coral Gables city commissioner in the upcoming April election.


One thought on “Florida 500: The Tamiami Trail

  1. Worth the visit is a restored Walking Dredge used to build the Tamiami Trail is on exhibit at the Collier-Seminole State Park and is a National Historic Mechanical Engineering Landmark.

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