Q: Which was first? St. Augustine or Pensacola? A: Neither!

San Miguel de Gualdape was the first European/African settlement in North America.

by Dale Cox

Was the first settlement of Europeans and Africans in
the continental United States somewhere near Sapelo Island,
home to the beautiful old Sapelo Island Lighthouse?
Joanne Dale / stock.adobe.com

The Florida cities of St. Augustine and Pensacola engage in a (mostly) good-natured debate over which is the oldest European community in the continental United States.

Pensacola stakes its claim on a settlement established there in 1559 by the explorer Tristan de Luna. The colony failed, however, and was abandoned until the return of the Spanish to Pensacola Bay in 1698.

St. Augustine, in turn, is the oldest continuously occupied European settlement in North America. Pedro Menendez de Aviles founded the ancient Spanish city in 1565, six years after Luna's attempt at Pensacola.

Both cities are beautiful, and both defend their claims with exceptional community pride. Pensacola was the site of the first settlement in today's Florida, even if it did not last. St. Augustine, on the other hand, has been there for 355 years.

Spanish settlers first built the city of San Miguel de Gualdape
somewhere on the Georgia coast in 1526.

Each city has a basis for its claim. Neither, however, was the first European settlement in the continental United States. That title belongs to San Miguel de Gualdape, a town settled somewhere on the Georgia coast in 1526.

It is worth noting, of course, that Native Americans were here for thousands of years before the first Spanish explorers. It should also be remembered that Juan Ponce de Leon - who later "discovered" Florida - founded Caparra, Puerto Rico, in 1508.

All but forgotten in United States history, Lucas Vazquez de Ayllon brought the first large scale colonization attempt ashore in what is now South Carolina on August 9, 1526.

It was a disaster from the start. Ayllon's flagship, El Capitana, wrecked on a sandbar, and the vital supplies aboard were lost. The colonists cut timber and built a replacement vessel. Christened La Gavarra, she was the first tall ship built in the continental United States. The provisions and other supplies, however, could not be replaced.

Lucas Vazquez de Ayllon 

Ayllon brought 600-700 men, women, and children with him, and they began to sicken and die almost immediately. Food supplies evaporated, and the site of the initial landing did not look promising for long-term occupation. Exploring parties were sent out, bringing back intelligence of a more-suitable location on a mighty river some 200 miles to the south.

Ordering his ships to carry the women, children, and sick down the coast to the new location, Ayllon mounted the able-bodied men on his remaining horses and started overland to meet the ships at the river described by his scouts.

The new site was somewhere on the coast of the modern state of Georgia. Most historians identify Ayllon's river with today's Sapello Sound, but the mouth of the Altamaha River and St. Simons Sound are also possibilities.

The new city was christened San Miguel de Gualdape on September 29, 1526, the day of the Festival of St. Michael. Archaeologists are searching for its site, but have yet to find it.

The Altamaha River flows past Darien, Georgia. The town of
San Miguel was somewhere in the area.

Things did not go well for the settlers of San Miguel. Starvation stalked the settlement, and the death rate soared as the colonists suffered from disease and exposure. They also made matters worse by forcibly taking food from local Native American communities.

Lucas Vazquez de Ayllon died at San Miguel de Gualdape on October 18, 1526. Hundreds of the other colonists went to the grave with him.

San Miguel was abandoned in November 1526 after a series of mutinies and North America's first-recorded slave uprising. Only 150 of the settlers survived to make it back to the Spanish settlements in the Caribbean.

The attempt to found a settlement on the Georgia coast ended in death and failure more than 30 years before Spanish soldiers set foot at Pensacola or St. Augustine.

The map below shows Sapello Sound, where many scholars believe the colony was located:

African slaves in Florida before St. Augustine?

"Africans of unrecorded countries."

by Dale Cox

Fort Caroline National Memorial commemorates the ill-fated
French attempt to settle on Florida's St. Johns River.

Did France bring African slaves to Florida more than fifty years before the "first" slaves reached Virginia in 1619?

An enigmatic passage in the deposition of a settler who arrived in 1564 - one year before the founding of St. Augustine - suggests that slaves helped build a short-lived French settlement on the St. Johns River. The colony was called Fort Caroline, and it stood in present-day Jacksonville.

Slavery was not particularly new in North America when the French arrived on the Atlantic seaboard of today's United States. Hernando de Soto infamously enslaved hundreds of Native Americans during his brutal march through the Southeast, even using the weak as food for his dogs. Other Native Americans from the region were carried away as slaves by Spanish vessels that stopped along the coast to fish or trade. 

The first recorded European settlement in North America, in fact, was neither Pensacola nor St. Augustine and certainly not Jamestown or Plymouth. It was San Miguel de Guadalupe, a colony founded somewhere on the Georgia or South Carolina coast in 1526. Meager Spanish records verify that some African slaves accompanied the expedition and that its commander, Lucas Vasquez de Ayllon, intended to kidnap hundreds of Native Americans to send into slavery.

The St. Johns River, which the French called the River May.

San Miguel, like the first effort to settle Pensacola in 1559, failed, and the survivors sailed away.

The French came next, building Charlesfort at today's Marine Corps Training Base at Parris Island, South Carolina, in 1562. The colony lasted less than one year, but the French came back with a greater determination just two years later.

The site they selected this time was a low triangular island on what they called the River May. This early designation for the St. Johns River survives in today's community of Mayport and Naval Station Mayport, both located near the river's mouth. Led by Rene de Goulaine de Laudonniere, the settlers formed an alliance with local Timucua Indians and started building Fort Caroline.

Among the early French settlers was a man named Robert Melenche. He later gave a deposition about the founding of the colony:

A modern ship passes beneath the guns of Fort Caroline. A
recreation of the fort stands near the original site.

…In this armada they brought three ships; the General's ship was a galleon of over 200 tons, although it was not a vessel for mercantile traffic because it had been built for war. Another was a 120-ton ship, and still another, an 80-ton ship. Three hundred men went out in this armada, 110 sailors, 120 experienced soldiers, and the rest of them, officers of various rank. Besides these, there were many Africans of unrecorded countries. [1]

The last line of this excerpt is of particular note. Who were the "many Africans of unrecorded countries" put ashore in Florida by France in 1564? Not even one of their names is known, and Melenche says nothing more about them. France was engaged in the African slave trade by the time, and Melenche's failure to include the "many Africans" in his enumeration of the 300 men sent to America suggests they were slaves.

A gruesome fate awaited the colonists of Fort Caroline - and undoubtedly many of the Africans as well.

Many of the settlers died of sickness and malnutrition during the winter of 1564-1565. Others mutinied and sailed away. The survivors were about to give up when a relief expedition arrived in August 1565.

The earth and timber walls of the fort proved no match for
the Spanish soldiers that attacked on September 20, 1565.

At roughly the same time, however, the Spanish arrived just down the coast and founded St. Augustine. Determined to wipe out the French, who he regarded not only as interlopers but as heretics because they were Protestants, Spain's commander Pedro Menedez de Aviles led 500 men overland to Fort Caroline.

The Spanish soldiers advanced through rough terrain and torrents of rain, reaching a pond near the fort on September 19, 1565. They stormed Fort Caroline on the next morning, slaughtering virtually every man they found. Some forty or fifty of the French escaped over the walls and into the surrounding wilderness. Laudonniere was among them.

The only other survivors were in a group of 60 women and children spared by Menendez. Everyone else died, and Fort Caroline was no more.

The fate of the slaves of Fort Caroline is unknown. Most probably died in the massacre or in two subsequent slaughters carried out by Menendez against French shipwreck victims. A handful may have been among the survivors.

The site of the ill-fated French settlement has never been found, and many believe that it has been washed away by erosion. The story, however, is commemorated at Fort Caroline National Memorial in Jacksonville. It is a unit of the Timucuan Ecological & Historic Preserve and is open to the public daily.

For more information, please visit the park's website:   https://www.nps.gov/timu/learn/historyculture/foca.htm.

How Ocheesee almost replaced Tallahassee as capital of Florida

The wooden frame capitol building in Tallahassee as it
appeared in 1831 when Ocheesee almost became state capital.
State Archives of Florida

Tallahassee had been capital of Florida for fewer than ten years when it almost lost the title to the Apalachicola River valley.

Pensacola and St. Augustine had never been thrilled that the new town being carved from the wilderness had taken their ancient titles as the twin capital cities of Florida. The population boom taking place in in Tallahassee, however, was rapidly solidifying its status.

The 1830 census revealed that Leon County, of which Tallahassee was the county seat, had become Florida's most populous county with 6,494 residents. Gadsden County was next with 4,895 while Jackson County was third with 3,907. 

Pensacola and St. Augustine had had lost their centuries old positions as the population centers of Florida in just nine years.

Florida as it appeared in 1832.
(Click to enlarge)

Anti-Tallahassee delegates to the Florida Territorial Legislative Council knew that 1831 might be their last chance to wrest the title of capital away from the growing town in the hills of Middle Florida. When the Council members convened that year, they took their best shot.

The delegates met at the tiny frame capitol building in Tallahassee in 1831 and voted for the appointment of a commission to review other potential sites for the establishment of a permanent capital city. 

The members of this commission began their work and three places quickly emerged as the leading candidates to replace Tallahassee. They were Ocheesee Bluff in Calhoun County, Mt. Vernon (Chattahoochee) in Gadsden County and an unidentified point on the Suwannee River. 

Mt. Vernon, which was soon renamed Chattahoochee due to mail confusion with the Alabama community of the same name, was the only one of these places that had become an actual town by 1831. It had been picked to become the site for Florida's new U.S. Arsenal and the arrival of steamboat traffic on the Apalachicola River spurred its growing development as an important river port.

The red clay of Ocheesee Bluff in Calhoun County, Florida.

Ocheesee Bluff, until recently the site of the Creek Indian village of Ocheesee Talofa, was also located on the Apalachicola River. The Federal Road crossed the river at Ocheesee, which was soon to be named the seat of government for short-lived Fayette County. 

Interests from the East Coast of Florida favored a location somewhere on the Suwannee River. A city there would have to be built from scratch, but unlike Tallahassee would be closer to St. Augustine, Jacksonville and Fernandina while also offering the advantage of river transportation.

It was a close decision:

SEAT OF GOVERNMENT. - The Commissioners appointed under the Resolution of the last Council have made separate reports - one infavor of Mount Vernon - two infavor of Ocheesee and one infavor of a point on the Suwanee as the seat of Government. - (Tallahassee Floridian, January 10, 1832).

This historic live oak tree at Ocheesee Bluff survives from
the days of the town of Ocheesee, Florida.

Three of the four commissioners favored a location on the Apalachicola River, but split between Mt. Vernon and Ocheesee. The latter place received a plurality of the total vote, but since the commission included four members it ended in a tie with Mt. Vernon and a site on the Suwanee.

Unable to break this deadlock, the Council delegates themselves decided to wait another year or two and see what might happen:

...The public buildings at Tallahassee will answer, until the progressive improvement of the Country shall show what point is likely to continue central, as regards the population of the Territory. - There are immense bodies of unexplored land of good quality in East Florida, and the Suwanee will probably be the center of population within ten years. - (Tallahassee Floridian, January 10, 1832).

The restored gunpowder magazine of the U.S. Arsenal at
Chattahoochee is now the Apalachicola Arsenal Museum.

It was not to be. The next ten years saw Leon County's dramatic growth continue while neighboring Jefferson County surged past Jackson to become the third most populous of Florida's counties. The St. Joseph Convention approved a proposed constitution for Florida and the territory was admitted to the Union as a state in 1845.

Ocheesee lost its chance to become capital of Florida by a single vote. Had the Apalachicola River supports on the commission unified their votes, the state capitol building would likely be there today. Instead, it is a ghost town. An old oak tree at Ocheesee Landing and the historic Gregory House across the river in Torreya State Park are virtually all that remain to prove it ever existed. 

Columbus, the town that soon grew on the Suwannee River, is also a ghost town today. Its cemetery and a few other traces can be seen at Suwannee River State Park.

Chattahoochee still survives as a small but charming city of just under 4,000 people. Its trail system has been named one of the finest of any small town in America and the Apalachicola River is both a Florida Blueway and a National Scenic Trail.

Tallahassee remains the state capital of Florida.

You can learn more about the ghost town of Ocheesee and Chattahoochee's historic River Landing Park in these videos from TwoEgg.TV:

#82 The Pensacola-St. Augustine Road (100 Great Things about Jackson County, Florida)

A surviving section of the Pensacola-St. Augustine Road

The historic Pensacola-St. Augustine Road is #82 on our list of 100 Great Things about Jackson County, Florida.

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

In 1778 the American Revolution was underway and its outcome was far from certain. While most Americans of today have heard of the 13 Colonies and their fight for independence from Great Britain, few realize that there were other colonies in North America that did not join the war against King George III.

1776 map shows East and West Florida

East and West Florida were both British colonies when the Revolutionary War began and both remained loyal to King and Country throughout the conflict. Founded by the Spanish, the Florida colonies had passed to the control of Great Britain at the end of the French & Indian (or Seven Years) War in 1763.

The British administered Florida as two colonies. East Florida extended from the Atlantic Ocean to the Apalachicola and Chattahoochee Rivers, while West Florida extended from the Apalachicola and Chattahoochee all the way to the Mississippi. What is now Jackson County formed the northeastern corner of British West Florida.

Purcell-Stuart Map of 1778, showing the Pensacola-St. Augustine Road

The only two cities in all of present-day Florida were Pensacola and St. Augustine. To link them, the British connected a series of Indian trails and parts of the Old Spanish Trail to form a new road that they called the Pensacola-St. Augustine Road. This early "super highway" was the predecessor of today's U.S. 90 and I-10.

Heritage Village in Graceville
A stop on the Jackson County Spanish Heritage Trail

In Jackson County, the route of the Pensacola-St. Augustine road is roughly followed by today's State Highway 2. It crossed Holmes Creek into the county where Graceville stands today and crossed through the modern sites of Campbellton and Malone before reaching the Chattahoochee River at Neal's Landing, where the Creek Indian town of Ekanachatte ("Red Ground") stood at the time.

The road was mapped in 1778 when a British force marched across Florida from Pensacola to reinforce St. Augustine against an expected attack by American Patriots. Accompanying that expedition was cartographer Joseph Purcell and his map of the Pensacola-St. Augustine Road provides a fascinating look back through time.

In western Jackson County, using Purcell's map as a guide, it appears that the historic road generally followed modern State Highway 2 east from Graceville to Campbellton. What is now Holmes Creek was shown on the map as the "Weekaywee Hatchee." This Hitchiti Creek term means "Spring Creek" or "Spring River." If the name looks familiar, there is a reason. Today's term Weeki Wachi (as in Weeki Wachi Springs) is a corruption of the Creek term Weekaywee Hatchee.

Coosa Old Fields (today's Campbellton)
As shown on the Purcell-Stuart Map of 1778

The road between Holmes Creek and today's Campbellton was described by Purcell as "small and little trod." Where Campbellton stands today, the map shows that in 1778 was a place called the Coosa Old Fields.

These "old fields" had been the site of the Spanish conversion or part-time church of San Antonio. The Chacato inhabitants who lived there had fled the area in 1675 following a rebellion against the Spanish missionaries. Most of them wound up living on the Coosa River in Alabama. Living on the Coosa Old Fields when Purcell passed through was a small band of Creeks who had a village on the site of present-day Campbellton that they called Puckanawhitla ("Peach Tree").

Forks of the Creeks swamp

From Campbellton the road followed the approximate route of today's State Highway 2 east, but as it neared Marshal Creek it veered to the southeast. Today's St. Phillips Road is an actual part of the original Pensacola-St. Augustine Road.

The route by which the road crossed the Forks of the Creeks swamps is no longer in use today, but Purcell noted crossing what he called the "Chanpooly" (today's Chipola River). The creek that he called the "Chanpooly" was today's Cowarts Creek, a main tributary of the Chipola.

Trace of Pensacola-St. Augustine Road
Notice State Highway 2 through the trees at left.

From the Forks of the Creeks to the Chattahoochee River, the old road roughly followed the route of today's State Highway 2. A section of the original can be seen running along the north side of the modern highway in the vicinity of its intersection with Pleasant Ridge Road.

The road passed through the modern town of Malone and continued on to the Chattahoochee River. The section of Biscayne Road between Concord Road and the point where Biscayne intersects with State Highway 2 is a part of the original Pensacola-St. Augustine Road that is still in use today.

Chattahoochee River at Neal's Landing Park

The historic roadway reached the Chattahoochee River at today's Neal's Landing Park. There in 1778 stood the large Creek village of Ekanachatte and the trading post of its chief, an individual called "The Bully" for his prowess as a businessman. It is a little known fact that British troops camped at what is now Neal's Landing during the American Revolution.

The Pensacola-St. Augustine Road was replaced in the 1820s by the Old Federal Road and still later by U.S. Highway 90 and eventually Interstate 10, all of which followed more direct routes between Pensacola and St. Augustine. Its surviving portions, however, remain important historical landmarks in Jackson County that date from before the time of the American Revolution.

Jackson County Spanish Heritage Trail (in red)
Click to Enlarge

Today's Jackson County Spanish Heritage Trail commemorates in part the historic roadway. A 150-mile driving tour that connects eleven important historic sites from the Spanish era, part of its route follows State Highway 2 from Neal's Landing Park to Graceville.

An interpretive kiosk has been erected in Malone to tell the story of the Pensacola-St. Augustine Road. It stands in the city park facing Highway 71, one-half block south of Highway 2. Malone is a great place to stop for lunch while driving the Jackson County Spanish Heritage Trail.

If you are interested in learning more about the new Jackson County Spanish Heritage Trail, guide books are available for free at the historic Russ House and Visitor Center on West Lafayette Street in Marianna. You can also learn more by visiting the Spanish Heritage Trail section of the TDC website at:  http://visitjacksoncountyfla.com/heritage/spanish-heritage-trail.

#97 Daniel Boone's Long Walk (100 Great Things about Jackson County, Florida)

Daniel Boone
Painted in old age by Chester Harding

#97 on our list of 100 Great Things about Jackson County is Daniel Boone's Long Walk. Click here to read previous posts in this series.

It is a little known fact that in 1765 (250 years ago next year), the famed American explorer and pioneer Daniel Boone passed through Jackson County on his long walk across Florida. He later told the story of the journey to his son, Nathan Boone, who recorded it along with many of his father's other memories.

After 250 years of Spanish rule, Florida was surrendered to Great Britain at the end of the French & Indian War in 1763. Spain had sided with France in that conflict and lost Florida as a result.

As the British took over the colony, a steady flow of settlers began to move down from Georgia, the Carolinas and even Virginia. Pensacola and St. Augustine were the primary destinations of these settlers, but others spread out through the back country where they were welcomed by the Lower Creek and Seminole Indians. The British were on good terms with the American Indians who lived in Florida.

Daniel Boone and his dog
Drawing by Alonzo Chappel

Two years after Great Britain gained control of Florida, Daniel Boone joined a party of men headed south on a journey of exploration. He then lived in North Carolina, was 31 years old and had survived Braddock's Defeat, the bloody ambush and defeat of British troops portrayed in the book and movie, Last of the Mohicans. Boone, in fact, was the primary model for the hero of the story, Natty Bumpo (renamed Nathaniel Poe for the movie).

Contrary to legend, Daniel Boone did not wear a coonskin cap. He was from a Quaker family and wore a flat brimmed hat. He had blonde hair and blue eyes.

Boone and his fellow travelers came south through Georgia to St. Augustine. From there, with Boone leading the way, the men set out on a more than 400 mile journey to Pensacola through the vast Florida wilderness. They were following a trail called the Pensacola-St. Augustine Road.

The "road" was really little more than a footpath that wound its way west from St. Augustine to the Suwannee River and then on to Lake Miccosukee near present-day Tallahassee. From there, the trail split into two paths, both of which angled north into what is now Decatur County, Georgia, before reuniting just outside the city of Bainbridge.

Daniel Boone leading a party of settlers
Painting by George Caleb Bingham

A settler and trader named James Burges (or Burgess) had settled where Bainbridge stands today and the explorers crossed the Flint River at his settlement. They then followed the trail on past the present site of Donalsonville, Georgia, and crossed the Chattahoochee River into Jackson County and back into Florida at Ekanachatte ("Red Ground"), a Lower Creek village at what is now called Neal's Landing.

Assuming that Boone and the other men remained on the main trail, from Neal's Landing they passed west along the route of today's State Highway 2. Their journey would have taken them across the sites of today's towns of Malone, Campbellton and Graceville. They crossed Holmes Creek out of Jackson and into Holmes County near Graceville.

1778 Map of the road followed by Boone

None of these towns or counties existed then, of course, and the only people that Boone encountered in what later became Jackson County were the Creek Indians who lived at Ekanachatte and at a small town called Pucknawhitla ("Peach Tree") which stood on the present site of Campbellton.

Section of road followed by Boone through Jackson County

The journey was long and difficult. At one point Boone and the others lost track of the path and became confused in the wilderness. He later told his son Nathan that he never was lost in his life, but was confused once for a few days.

Daniel Boone had not been impressed with the lands he saw between St. Augustine and the Chattahoochee River, but once he crossed into what is now Jackson County he found richer lands and pristine forests. Deer and other animals were plentiful and the pioneer was impressed.

Daniel Boone from Life
Painting by John James Audubon

After the group reached Pensacola, Boone made arrangements to acquire land in West Florida (the British divided the modern state into two colonies, East Florida and West Florida). He planned to relocate to the area and become one of its first English settlers.

The explorer's wife, Rebecca, had other ideas. She firmly objected to the move because it would take her so far from her family in North Carolina. Boone complied with his wife's wishes and the idea of moving to Florida was abandoned.

Other members of the pioneer's family, however, would follow in his footsteps. Among the earliest American settlers of Jackson County was Gilley Crawford Boone Neel, a member of Boone's family. She first settled with her husband and children near Neal's Landing and later lived in the Paront community north of Grand Ridge. She and many other relatives of Daniel Boone are buried at Cowpen Pond Cemetery near Dellwood.

Great Oaks in Greenwood, Florida

Other relatives of the famed pioneer and his wife settled in Greenwood. Rebecca Bryan Boone was a member of North Carolina's noted Bryan family. That family was instrumental in the founding of Greenwood and Great Oaks, a beautiful antebellum home, was originally the Bryan Mansion. Members of the Boone and Bryan families are buried in numerous cemeteries around Greenwood.

The historic Pensacola-St. Augustine Road, which Boone followed across Florida, is interpreted on the new Jackson County Spanish Heritage Trail. A kiosk at City Park on Highway 71 in downtown Malone tells the story of the historic road.  Click here for more information.

Daniel Boone's long walk is an almost forgotten footnote of Florida history, but it is one of the 100 Great Things about Jackson County, Florida.