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Surf, Sun, and a Long History of Fun at Pensacola's Fiesta of Five Flags

By David Boegaard

Many people know Pensacola, Florida as home to beautiful, white-sand beaches, temperate winters, and the broad Pensacola Bay. Few people know that Pensacola is the first settlement established by Europeans in the US. But the Spanish failed to hold onto the territory for long, and over the years the area was ruled variously by the British, French, Confederate States and United States governments. It should be no surprise, then, that Pensacola has long called itself the City of Five Flags. And each year the people of Pensacola get together to put on the Fiesta of Five Flags, a festival celebrating the long and rich history of the region. With dancing, food, a parade and a Fiesta Court, the Fiesta of Five Flags has something for everyone.

The first settlement by Europeans was led by a Spaniard traveling from Mexico with thirteen ships and more than 1,500 soldiers and colonists. "In 1559, Spanish Conquistador, Don Tristan de Luna, established Pensacola as the first European settlement in the United States," says Margaret-Anne Dyson, Marketing Coordinator for the Fiesta. The name Pensacola comes from the name given to the region by the Muskogean-speaking indigenous peoples living in the area at the time.

Unfortunately for the Spanish, Don de Luna ran into trouble early. The indigenous people resisted the settlers, and they suffered the loss of almost half their ships and hundreds of men in a hurricane. After a rough winter, famine, continued attacks by the locals, and even a mutiny, Don de Luna and his remaining men left the region for other adventures.

It wasn't until 1698, almost 150 years later, that Europeans again tried to settle Pensacola. By that point, the Spanish colonial aims were under severe pressure from French colonists in the Gulf of Mexico coastal region. The Spanish set out to establish a new fort and colony in the broad Pensacola bay, and this time they were successful. The vast majority of Spanish settlers were men, so they sensibly created a creole culture permissive of relationships with the local indigenous people, called the "Pensacola" people, and with African slaves, some of whom were given refuge in Florida in exchange for conversion to Catholicism and military service. This mix created a rich blend of race and culture.

The French briefly took the Pensacola region, however, in 1719, attacking from French Louisiana. Their control was weak, however, and they retreated by 1721.

By 1763, the French had lost the French and Indian war, and the Spanish ceded Pensacola to the British, who now controlled the regions previously held by the French. The British so valued Pensacola that they established it as the capital of their new West Florida colony.

But with the Revolutionary War beginning in 1776, the Spanish joined the American side and retook Pensacola in 1781, and kept it until the United States bought Florida from the Spanish for $5 Million in 1819. IN 1821, Pensacola became a territory of the United States, governed by future president Andrew Jackson.

At the time, Pensacola was still a heavily mixed-race region, but tensions increased between the increasingly white immigrants and the more mixed-race long-time inhabitants. Finally, an 1853 bill prohibited Indians from living in Florida.

By the time Florida joined the Confederacy in revolt against a proposal to cap the number of slave states, Pensacola had truly become a part of the South. After the brutal fight to preserve slavery, the Confederates resigned and Pensacola became what it still is today, a beautiful sunny city in the United States.

Today, Pensacola is not only a place of beautiful, white-sand beaches, but the proud location of the first Naval Air Station, where John Glenn and Neil Armstrong trained and where the Blue Angels call their home.

This incredible history is the backdrop to Fiesta of Five Flags each year. The festival remembers Pensacola's long history, but especially the initial founding settlement by Don de Luna. "In 1949," says Dyson, "Calvin Todd, President of the Pensacola Chamber of Commerce, proposed the concept of combining a historical theme with tourism promotion."

Since then, the Fiesta increased its scope, says Dyson. "The Pensacola Crawfish Festival in the spring and the Pensacola Seafood Festival in the fall are both three-day events held in the historic district of downtown Pensacola." These events are not only great fun and wonderful for the community, but they help raise fund for the Fiesta of Five Flags, notes Dyson. "The success of these weekend events has enabled Fiesta to invest in local organizations that research and promote Pensacola's history."

A big part of the fun of the Fiesta of Five Flags is the Fiesta Court. Each year, the Fiesta elects a court with king and queen and other court members. As is appropriate for royalty, the court is not democratically elected. Rather it is selected by a committee of past court members. "Any past member of the Fiesta court may nominate new members," says Dyson. "Depending on the number of nominations, a selection committee decides who will become court members based on their participation at Fiesta events, ranging from volunteerism to sponsorships."

This helps ensure that the people who represent the Fiesta Court are genuinely engaged in Pensacola and the activities surrounding the Fiesta. "Volunteerism is the cornerstone of Fiesta," notes Executive Director Adelene Lovelace, "therefore the tradition of court membership helps sustain the perpetual success of our organization." Naturally, the Fiesta of Five Flags honors the old traditions.

The Fiesta is a ten-day celebration, with events ranging from the historically minded to the pure fun. But the best part comes at the end -- the DeLuna Coronation Ball. "Each year, court members represent important members of Pensacola history," says Bridget Middleton, Event Coordinator for the Fiesta. "During the historical presentation, their contributions to our city are highlighted."

This mix of tradition, fun and sun is the reason people have come to love Pensacola. And the Fiesta of Five Flags works to keep those traditions alive for many years to come.

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