The barrier islands of Franklin County harbor mysteries from times gone by, as the two ship’s hulls unearthed on Dog Island by Hurricane Michael remind us.

However, neither hull belongs to the two oldest known shipwrecks, namely the 1766 wreck of Le Tigre that stranded Pierre Viaud, and the 1799 wreck of H.M.S. Fox that left privateer William Augustus Bowles, Captain James Wooldridge, and at least 50 crewmen to fend for themselves on St. George Island.

Luckily for the Fox’s crew, President Thomas Jefferson had sent the Southern Boundary Commission, headed by surveyor Andrew Ellicott, to mark the boundary between U.S. and Spanish territory along the 31st parallel and the Florida border. Accompanied by Spanish troops and Creek Indians, Ellicott’s party had reached the Apalachicola River just before the Fox went aground. Owing to hostilities with the Lower Creeks and Seminoles, Ellicott headed downriver and came to Bowles’ aid.

At age 13, Bowles had joined the British Army to fight in the American Revolution, and was stationed in Pensacola at the end of the war. Apparently, he rebelled against military authority and deserted, walking alone into Creek territory. After the Creeks rescued him, he stayed with them and married the daughter of Chief Samuel Perryman. Always brash, Bowles became a chief and conceived the idea of founding an independent Nation of Muscogee, naming himself Director General.

When Britain was forced to return Florida to Spain, Bowles determined to help the Creeks regain their territory from the Spanish and defend it against the encroaching Americans. At the time, the Creeks preferred English trade goods over Spanish ones, and obtained their supplies from Panton, Leslie and Company’s store in Pensacola. Bowles viewed Panton, Leslie and their young partner, John Forbes, as rivals, and promised the Creeks that he could supply them with comparable goods.

By 1799, Bowles had obtained some backing for his plan from the British crown and business partners in Nassau in the Bahamas. In early September, he loaded arms and rum for the Creek nation onto the HMS Fox. The ship was a 150-ton schooner armed with 16 cannons that was commanded by British Lieutenant James Wooldridge. Under way to the Apalachicola River, the ship encountered a violent storm. The captain reduced the rigging and attempted to steer through the channel at East Pass, but the ship foundered on a shoal at night.

In an attempt to refloat the ship, Wooldridge ordered the crew to jettison most supplies and armaments. Bowles was outraged, but when the storm let up, the crew of at least 50 men managed to reach shore and salvage several barrels of gunpowder, lead ball, and rum intended for the Creeks.

By September, Ellicott’s survey crew had reached the western bank of the Apalachicola River, and encountered hostile bands of Creeks. Fearing for their lives and loss of their instruments and records, they decided to rejoin their survey ship at St. Marks. In a small Spanish schooner that could navigate the Apalachicola River, the surveyors headed to the river mouth, where they stopped to repair the rigging.

Fortunately for Bowles and the crew of the Fox, Ellicott had sent his supply ship, the Sally, ahead to St. Marks. When its captain did not hear from the surveyor, he sent a small boat looking for them, and the sailors noticed the Fox’s crew on St. George. Bowles and Wooldridge wrote letters to Ellicott explaining their predicament. The American sailors found Ellicott at the mouth of the Apalachicola River and delivered the letters, which read in part:

“I am at present on a small island… which is well known to the bearers of this letter… his Britannic Majesty’s schooner Fox, late under my command, was unfortunately wrecked five days since, on this coast. As there is no possibility of saving the schooner, I trust sir, your humanity will induce you to stop here and devise with me some means of removing these unfortunate men, who have nothing more than some provisions from the wreck to exist on.” (James Wooldridge, Lieutenant in the Royal Navy)

“Sir, I am now at the mouth of this river on my return from Spain… in order once more to rejoin my nation the Creeks… having saved all my effects, with my boat, should have proceeded into the country, until hearing of your being near… wish much to see you. Although we may differ in politics, yet as gentlemen we may associate… at least we may be civil to each other, I pledge my honour to be so to you and rely on yours.” (Wm. A. Bowles)

Ellicott supplied the camp with a barrel of pork and other provisions, but a gale arose that forced him to remain on St. George Island for eight days. Being a surveyor, he recorded the latitude and longitude of the camp in his journal. The latitude places the camp near Marsh Island, which was then at the eastern tip of St. George.

In 1799, Britain was at war with Spain and the United States was neutral. Therefore, Ellicott told Wooldridge and Bowles that the best he could do was to offer some of his food and supplies, and he notified them that he expected his supply ship to arrive soon. He requested that the men leave the second ship alone and find other means to return to their home ports. Ironically, Ellicott had obtained a supply ship named the Shark from Bowles’ rivals, Panton, Leslie and Company.

Accounts of what happened next differ. Ellicott rejoined the crew of the Sally at St. Marks. When his supply ship did not arrive, the crew loaded salted beef and wheat flour for the trip south. The beef spoiled, and by the time the ship reached the Matecumbe Keys, the crew was subsisting on bread, fish and small deer they were able to shoot.

On Nov. 8, Ellicott reported that he saw his expected supply schooner, the Shark, “late the property of Messrs. Panton, Leslie and Company, of Pensacola… being a prize to Lieut. Wooldridge and crew… who had captured her near St. George’s Island on her way to Apalachy (St. Marks). The schooner was loaded with provisions, and as we had no meat, our commissary made application to the prize master for a barrel of pork; but the prize master Mr. Barnes made no direct answer, but said he would see about it the next day.”

Early the next morning, Wooldridge and the Shark sailed away without aiding the men who had helped them when they were stranded on St. George Island. “Thus we were requited for our favors,” Ellicott wrote. Fortunately for his men, the next day he encountered a privateer who sent over a barrel of pork, and the ship turned north and made it safely to St. Mary’s, where he completed his survey of the U.S. boundary without further trouble.

Bowles was not on board the Shark during the second encounter. He had obtained a pirogue from his followers along the Apalachicola and Wakulla rivers, and they distributed the barrels of rum, ball and powder among the Creeks. John Forbes, then a partner with Panton, Leslie and Company, conspired with friendly Creeks and the Spanish authorities to capture Bowles. The adventurer was delivered to Morro Castle in Havana, where he died in 1805.

In the years since 1799, the end of St. George Island has extended eastward about a mile towards Dog Island, closing the pass to about two miles. Bowles’ camp on Fox Point has never been located, and it is unknown whether the campsite and the Fox are buried by sand on the island or along the shore in the Bay or the Gulf. Surveys conducted by a Florida State University underwater archeology team from 1999 to 2001 located a number of artifacts that turned out to be World War II debris and a winch from a modern fishing boat.