Pirate Ghosts of the Emerald Coast

Headless Pirates haunt Santa Rosa Sound

by Dale Cox

Santa Rosa Sound at Fort Walton Beach, Florida.

Editor's Note: October is Monster & Mystery Month on Two Egg TV! Check back daily for new stories of monsters, mysteries, and more from Florida, Alabama, and Georgia.

Santa Rosa Sound is a beautiful natural waterway that extends east from Pensacola Bay past Mary Esther and Fort Walton Beach to Choctawhatchee Bay. It separates the sparkling white sand beaches of Santa Rosa Island and the rising condominiums and hotels of Okaloosa Island from the prehistoric Native American mounds and waterfront of Fort Walton Beach.

This stretch of water is a popular playground today, but is it also the haunt of a band of headless pirates? Legend holds that just such a crew is condemned to perpetually sail its surface on moonlit nights. The following report of an encounter with these seafaring specters appeared in Florida and Alabama newspapers in 1921:

One night Mr. Lee Jernigan’s vessel was sailing up the sound, just drifting along. As they passed Pirates’ Cove a yawl came out of the cove and was rowed alongside. Mr. Jernigan was below. There were three men on deck, and they declared that every man in the yawl was headless that they watched the boat several minutes, when all at once—just like a flash—boat and men disappeared. The three men took oath, kissed the Bible, and swore that they saw this. [1]

Santa Rosa Sound on a "ghost story" perfect winter's day.

Pirates' Cove is a shallow body of water within the limits of today's Gulf Islands National Seashore. It is directly across Santa Rosa Sound from the City of Mary Esther, Florida. Entirely surrounded by the dunes of Santa Rosa Island, it is connected to the sound by a shallow inlet. 

The vicinity achieved note in 1906 after a significant storm exposed a cache of lost treasure:

...Spanish coins have been found in the sands of Santa Rosa Island, and only a few years ago, 1906, after a great storm twenty were found on the island in the sand. This find was on Santa Rosa Island, opposite Mary Esther. They were stuck together, showing that they had been buried for a long time aggregated in value several hundred dollars. Not far away is Pirates’ Cove, a little bay in Santa Rosa Island, so named because a pirate ship was sunk there.[2]

The Face of a Real Pirate
William Augustus Bowles as painted
in London in 1790.

The ghosts of the lost pirate and his crew, of course, are said to be searching for their lost cache of coins. They are presumed to also be protecting other treasures that remain hidden on Santa Rosa Island and along the shores of Choctawhatchee Bay. 

Anyone familiar with food and fun on the Emerald Coast is familiar with Fort Walton Beach's legendary Billy Bowlegs Pirate Festival. This fun escapade has been part of the local cultural scene since 1953 and celebrates the "life" and lore of a supposed pirate named Billy Bowlegs. The founders of the festival associated their event with the adventurer and pirate William Augustus Bowles, who prowled the waters of the Gulf of Mexico in 1799-1803. (Note: The real Billy Bowlegs was an important Seminole Indian chief. William Bowles never used the name).

So far as is known, Bowles never sailed from Choctawhatchee Bay, but the best pirate stories are not always the most authentic! The festival is fun and does exactly what its founders intended by bringing tens of thousands of visitors to enjoy a weekend in Fort Walton Beach.

Long before the pirate festival came into being, though, the ghost pirates were a force to be reckoned with for those sailing in Santa Rosa Sound. Strange lights were seen on the island at night in the vicinity of Pirates' Cove, and many fishermen swore to their own encounters with the spirits:

"You may ask any sailor who has passed Pirates’ Cove at night," continued the newspaper accounts, "and he will tell you of the lights and boat and headless men and if he has not seen them his ship mates have."

One man was so frightened by his encounter with the ghosts that local residents swore and began to tremble so badly that "he became bowlegged." 

If you want to see the pirate ghosts for yourself, just enjoy a midnight boat ride west from Fort Walton Beach down Santa Rosa Sound in the direction of the Navarre Bridge. The red pin on the map below points out Pirates' Cove.

Editor's Note: The lands surrounding Pirates' Cove are part of Gulf Islands National Seashore. Treasure digging is strictly prohibited and can lead to a lengthy prison term!

#84 The Pirate Billy Bowlegs in Jackson County (100 Great Things about Jackson County, Florida)

William Augustus Bowles

The pirate Billy Bowlegs is #84 on my list of 100 Great Things about Jackson County, Florida.

Please click here to see the entire list as it is unveiled.

Jackson County, of course, is inland from the Gulf of Mexico, yet it has the strongest connection of any place in Florida to the infamous pirate and adventurer William Augustus Bowles. He is the man celebrated in Fort Walton Beach today as the pirate Billy Bowlegs and is often confused with the Seminole chiefs of the same name.

How Bowles came to be called "Billy Bowlegs" is a mystery to me as there is no evidence he ever used the name during his lifetime. That point aside, however, he most definitely was a pirate.

Born in Maryland, he first came to what is now Jackson County during the American Revolution after he was thrown out of the British military. East and West Florida, divided by the Apalachicola and Chattahoochee Rivers, were then colonies of Great Britain. Spain's more than 250 year rule had ended in 1763 when it lost control of Florida in the treaty that ended the Seven Years' War (known in America as the French & Indian War).

Parramore Landing Park

Making his way east from Pensacola, Bowles likely was trying to walk home to Maryland when he became hopelessly lost in the vast wilderness of the Florida Panhandle. Rescued by Creek Indian warriors from the Perryman towns, he was brought to the Chattahoochee River.

The Perryman towns stood on opposite sides of the river near present-day Parramore Landing Park. Thomas Perryman, the half-Creek son of trader Theophilus Perryman, lived on the Georgia side of the river at what later became Fairchild State Park. His son, William, lived in what later became Jackson County at Tellmochesses, a Creek Indian town that stood on high ground back from the river just north of Parramore Landing.

Creek Indian village in Jackson County, Florida

Bowles became closely associated with both Thomas and William Perryman, both of whom had taken up arms along with their people on the side of the British in the American Revolution. By the time the future pirate reached their villages, they had fought against American Patriots in Georgia.

Bowles married into the Perryman family, becoming a son-in-law of Thomas Perryman and brother-in-law of William Perryman. He frequented their towns and was a regular fixture in the Creek Indian villages along the Chattahoochee and Apalachicola Rivers.

Flag flown by Bowles' pirate ships

In the years that followed, Bowles declared himself the "Director General" of the "State of Muskogee." In this capacity, he declared war on Spain and commissioned the "Muskogee Navy," really a flotilla of well-armed pirate ships that attacked merchant shipping in the Gulf of Mexico.

The Spanish Coast Guard sent armed ships to destroy Bowles and his nest of pirates, but the "Muskogee Navy" was too strong for them and proved victorious in a pitched battle at Apalachicola Bay. The Spanish retreated and the pirates continued their depredations.

Uniquely, the crews of the pirate vessels commissioned by William Augustus Bowles included not only white and African American sailors, but Creek and Seminole Indian sailors as well. While his "State of Muskogee" existed only on paper and in his mind, his ships sailed with diverse crews.

Bowles eventually was taken prisoner and died at El Morro Castle in Cuba. What became of his ships - except for one seized by the English in the Bahamas - is not known. His legend lives on at the Billy Bowlegs Festival in Fort Walton Beach and may soon be celebrated in a Pirate Festival being considered for Parramore Landing Park!

The little known fact that the Pirate "Billy Bowlegs" once lived in Jackson County is #84 on our list of 100 Great Things about Jackson County, Florida.

If you missed the earlier post about Bowles' lost pirate treasure, please visit Lost Treasure of the Money Pond.

#95 Lost Treasure of the Money Pond (100 Great Things about Jackson County, Florida)

The Money Pond in Jackson County, Florida

The lost treasure of the Money Pond is #95 on our list of 100 Great Things about Jackson County, Florida. Click here to see previous items on the list.

In the northeast corner of Jackson County, legend holds that a pirate treasure waits to be found deep beneath the mud and muck of a swampy body of water. Locals call the place the "Money Pond" and many believe there is enough gold and silver at its bottom to make the person who finds it an instant millionaire.

Spanish treasure on display
Museum of Florida History in Tallahassee

That is likely even more true today thanks to the astronomical price of gold, which at the close of the markets today was selling for $1,339.50 per ounce.  Silver closed at $20.89 per once. Legend holds that the pond contains 7 horse loads of gold and silver, each said to weigh over 100 pounds.

If true, that means there is somewhere around 11,200 ounces of gold and silver at the bottom of the Money Pond. If half of it is in gold, then the value for the weight of the metal alone would be nearly $8 million!

More Spanish Treasure at the Museum of Florida History

And that's just the beginning of the story. The actual value of the treasure could be much, much higher because each of the coins would be worth far more to collectors than the value of its weight alone. A much smaller hoard of three cans containing gold coins from the 19th century was recently found in California and is already thought to be worth more than $10 million.

So is the story true?  Is an unbelievable treasure waiting to be found at the bottom of a swampy Florida pond?

The answer to those questions may be... yes.

William Augustus Bowles
Self Portrait of the Pirate "Billy Bowlegs"

The story has its roots in the real life of the famed pirate and adventurer, William Augustus Bowles. He is celebrated in Fort Walton Beach today as the Pirate Billy Bowlegs, which often causes him to be confused with the later Seminole Indian chiefs of the same name.

Born in Maryland in around 1763, Bowles joined the British military service in 1776 when he was thirteen years old. That was the year, of course, that the United States declared its independence from Great Britain. Bowles was from a family of Tories, however, and his loyalty was to King George III.

According to an early History of the Bowles Family, he fought at the Battle of Monmouth, New Jersey, before traveling with his regiment from New York to Jamaica and from there to Pensacola. Spain had lost Florida to Great Britain at the end of the French & Indian War and it is a little known fact that East and West Florida remained loyal British colonies during the American Revolution.

According to family historian Thomas M. Farquhar, Bowles was driven from the British service following a dispute with one of his commanding officers. The exact details remain murky and there are several different versions of what happened.

Lower Creek village in Jackson County, Florida

Only 15 years old at the time, he decided to walk home to Maryland and set off on his own through the vast wilderness of the Florida Panhandle. He quickly became completely lost, but was discovered by a party of Lower Creek Indians from the Perryman towns. These villages, located in today's Jackson County, Florida and neighboring Seminole County, Georgia, were headed by Thomas and William Perryman. The son and grandson of English trader Theophilus Perryman and his Creek wife, the two Perryman chiefs were wealthy mestizos (a term meaning they were of mixed Creek and European ancestry).

Since the Creeks were on good terms with the English, the warriors carried Bowles to their towns and he quickly ingratiated himself with the Perryman family. He later married Thomas Perryman's oldest daughter and led the Perryman warriors during the Battle of Pensacola in 1780.

Flag flown by William Augustus Bowles

In 1791, at the age of 22, he traveled to London where he negotiated docking rights at British ports in the West Indies for ships flying the flag of what he called the "Creek and Cherokee Nation." These rights in hand, he traveled to New Providence in the Bahamas where he purchased a small sloop and began trading voyages back and forth to the Lower Creek towns on the Chattahoochee River.

On a more ominous note, however, he armed his vessel with cannon and soon entered the life of a pirate, capturing merchant ships on the Gulf of Mexico. He was very good at being a pirate and his one ship soon turned into a flotilla of pirate vessels.

To give these ships at least a semblance of legitimacy, he declared the independence of what he called the "State of Muskogee" and declared war on Spain. Florida had returned to Spanish control at the end of the American Revolution, but the British trading firm of Panton, Leslie and Company had remained behind. Turning his flotilla of pirate ships into the "Muskogee Navy," Bowles became a major thorn in their side.

He and his pirate crews, which included white, black and Creek Indian men, raided merchant vessels traveling in the Gulf. On one occasion they defeated Spanish coast guard vessels in a fierce battle on Apalachicola Bay. Among the vessels of his fleet were the warships Mackisuky and Tostonoke.

Ekanachatte in 1778
From the Purcell-Stuart Map

In one of his letters, Bowles mentioned plans to bring a ship loaded with cargo up the Apalachicola River to either the trading post of James Burges (Burgess) at what is now Bainbridge, Georgia, or a place he called "The Bully's" on the Chattahoochee River.

The Bully, so named for his prowess as a trader, was the chief of the Lower Creek town of Ekanachatte ("Red Ground") which lay on the west bank of the river at what is now Neal's Landing Park in Jackson County. He was a supporter and business associate of Bowles and was fabulously wealthy for his time.

Bowles became such a threat to Spanish and merchant shipping that a reward of $6,000 (in 1790s currency) and 1,500 kegs of rum were offered for his capture. He eventually was captured and died while on a hunger strike at the fort of El Morro in Cuba.

Chattahoochee River at Neal's Landing (Ekanachatte)

According to legend, however, his treasure remained behind at Ekanachatte (Neal's Landing). It stayed safe there until 1818 when, during the First Seminole War, the Creek troops of Brigadier General William McIntosh drove south into Florida as part of Andrew Jackson's invasion. Fearful that the treasure would be captured, the chief and warriors of the town sank it into the Money Pond.

McIntosh defeated the Ekanachatte warriors at the Battle of the Upper Chipola near Bellamy Bridge in March 1818 and the treasure was forever lost. See Battle of the Upper Chipola.

The Money Pond

The story, however, does not end there. During the early 1900s, two major expeditions were launched by treasure hunters to find the lost gold and silver of William Augustus Bowles. The largest of these arrived in northeastern Jackson County in 1927, dug a ditch and drained the Money Pond.  Once the mud had dried somewhat, they started digging... and found Spanish silver coins in the muck at the bottom of the pond!

Before they could recover the main treasure, however, it began to rain. 1927 is remembered today as the year of the Great Flood. From Louisiana east and the Ohio River south, flood waters rose to unheard of levels. In Jackson County, the Chattahoochee surged from its banks and flowed as far inland as Malone. The treasure dig came to an end as raging flood waters flowed through the swamps and forced the men to flee for their lives.  They never came back.

The treasure, it is said, is still there today.

To read more of the story of William Augustus Bowles and the Money Pond, please consider my book, The History of Jackson County, Florida: The Early Years.  It is available at Chipola River Book & Tea in downtown Marianna or online from Amazon.com by clicking here: (Kindle)The History Of Jackson County, Florida: The Early Years.

The Kindle version is available for instant download by clicking here: The History of Jackson County, Florida: The Early Years.

Ekanachatte, near the legendary Money Pond, is one of the stops on the new Jackson County Spanish Heritage Trail. The 150 mile driving tour passes 11 key Spanish colonial sites in Jackson County. The new guide booklet is available at the historic Russ House and Visitor Center in Marianna. Learn more online at http://visitjacksoncountyfla.com/heritage/spanish-heritage-trail/.