Celebrating 98 Years of the Tamiami Trail

“There isn’t enough fill in the face of the earth to build a railroad across the Everglades,” is a quote often attributed to one of Henry Flagler’s employees, after his attempts at constructing a rail line through the Everglades failed.

Sixteen years later, that all changed when the world’s “greatest highway” was finished on the leftover track Flagler had laid. And now, 98 years later, it means a chance for outdoor fun, which is exactly what transpired on Saturday, April 25.

“I love that Everglades City always comes together to celebrate these things throughout their history,” said Regina Bowden, a local volunteer. “They have a very rich history and culture, so anytime they plan to relish those events from the past, I find it invaluable.”

Tamiami Trail was completed on April 26, 1928. Barron G. Collier called it “the greatest highway that this splendid peninsula has ever possessed” in his opening day speech. Collier bankrolled the Trail’s completion in exchange for having a county named after him. The highway connecting Miami and Tampa radically altered South Florida’s economy, people, and trade, and gave us the name of the county we live in.

For the 98th anniversary celebration, the occasion was opened by the Caloosa Country band, the delightful duo of Joseph and Jane Winebrenner. Their collection of classics and improvised numbers lifted everyone’s spirits. People jumped in and sang songs side-by-side, including Sheriff Boylan, who vocalized a lovely version of “Daddy Sang Bass.”

Dozens of visitors and residents also bore witness to Everglades City’s most famous tradition: Laundry Cart Racing. Parents packed their children into laundry carts, and if they pushed more vigorously than the opposing family, they would see the checkered flag waved in their honor. The prize: more sullied clothes to clean.

Throughout the festivities, visitors would hear the roar of engines as multiple car clubs arrived on scene, showing off some beautiful and rare cars, like a new Morgan Plus-four, a Porsche 981, an ‘08 Bentley, and the star of the show: an anniversary edition of Toyota’s first car, the Model AA.

The party also served as a commemoration for event host Museum of the Everglades’ 28th anniversary. For arrivals lucky enough to be early, the Museum of the Everglades hosted a private tour guided by historian Thomas Lockyear. Guests described the tour as “insightful” and a “fascinating” way to relive Everglade City’s glory days as the seat of Collier County. This historically preserved site was once a commercial laundry room and features a new orchid exhibit: “Growing Obsession – The Enchanting Story of Orchids in the Everglades,” which runs through June 20.