Treasure of Choctawhatchee Bay

Do millions in gold and silver await discovery?

Choctawhatchee Bay in Northwest Florida.

by Dale Cox

Editor's Note: This article continues "Monstery and Mystery Month" on Two Egg TV! To read the first article in the series, please see Pirate Ghosts of the Emerald Coast!

Long before real gold rose from the sands of Destin and South Walton, Choctawhatchee Bay was the focal point of a series of searches for buried treasure. In fact, many would-be millionaires still believe that a fortune in Spanish gold and silver remains to be found somewhere in the bay.

The frenzy surrounding the purported treasure reached its height in 1921-1925 after a man named W.S. Teachout claimed to know its precise location:

Mr. Teachout, who is about seventy years of age, said he could go and put his hands on three of the ships--one that was under only a few feet of sand, that he found it several years ago, and was only waiting for someone with enough money to tackle the job. He was told that men and boats were at his disposal, and that dredges, pumps, and divers would be gotten if necessary. [1]

Rocky Bayou as seen from the shoreline at Fred Gannon
Rocky Bayou State Park in Niceville, Florida. The park is
one of the prettiest spots on Choctawhatchee Bay's north shore.

The legend, as told by Teachout, was that a flotilla of pirate ships was cornered in Choctawhatchee Bay by Spanish warships. East Pass was too shallow for the vessels to escape, and the Spanish had blocked the channel leading from the Choctawhatchee through Santa Rosa Sound to Pensacola. Instead of surrendering to face not just the loss of his treasure but his execution on the gallows at Pensacola, the pirate leader scuttled his gold-laden ships and escaped into the woods with his crew.

No documentation that the legend is true has ever been found, and there is a good reason for skepticism. Evidence, however, has never been a barrier to true believers!

Mr. Teachout found ready investors, and they met him at Valparaiso, ready to begin the search. That's when things got very strange:

...Wednesday night there was a dance in Valparaiso and several strangers were present, two of whom attempted to draw Mr. Teachout into conversation about the treasure. Thursday morning when a boat went out with Teachout and others an airplane soon appeared and hovered over the boat. The boat remained out all morning, and so did the plane. It hovered over the treasure seekers’ boat until noon, when the boat returned to Valparaiso, and the plane flew away. [2]

Did a flotilla of treasure-laden pirate ships meet its end
in Northwest Florida's Choctawhatchee Bay?

The 1921 search focused on areas along the north side of the bay between Valparaiso and Freeport. Newspaper writers reported seeing "mysterious figures," including one of a ship carved into large trees along the shore.

To his own chagrin, Teachout was not able to lead the searchers to the treasure, and the hunt came up empty. The effort to find gold and silver in the bay, however, was far from over. Things got hot again in 1925 when a mysterious dredge left Pensacola and made its way through Santa Rosa Sound to Choctawhatchee Bay:

…Movement of the big barge through the narrows of the sound is a costly process but it was accomplished, the first stop of the barge being at the south shore in Hogtown Bayou. In the past days the dredge has been working off Camp Walton [i.e. Fort Walton Beach]. 

     Lands on the north shore of Choctawhatchee bay, where old timers say treasure is really cached, are owned by the Dixie Town and Land company, and its officials have announced that they will permit no trespass of their properties or riparian rights. The barge crew has been warned not to come within 1,000 feet of this shore line or injunctions will be obtained against them. [3]

The north shore of Choctawhatchee Bay is said by some to be
the location of a mysterious buried treasure.

Part of the north shore of the bay - then as now - was the property of the U.S. Government. Military officials were so concerned about the treasure seekers that they launched planes to shadow their movements. This might also explain the mysterious aircraft that followed the 1921 expedition.

The expense and determination expended on the 1925 expedition failed to bring treasure up from the bottom of Choctawhatchee Bay. The search came up empty, and legends of buried treasure continue to this day.

Is there really a buried treasure? And if so, who could have left it there? The only real answer to the first question is that anything is possible. No documentation of Spanish ships cornering a pirate flotilla in Choctawhatchee Bay has ever been found, but it is challenging to prove a negative. As to who could have left it there, legend current in 1925 credited the famed Louisiana pirate Jean Lafitte.

Editor's Note: Watch for another mystery tomorrow right here on our web channel at www.twoeggflorida.com. 

REFERENCES

[1] Wiregrass Farmer quoting the Valparaiso Herald, September 8, 1921.

[2] Ibid.

[3] The Tampa Times, September 12, 1925.

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.