Published by former Mayor George Gardner July 26 2016
The Report is an independent publication serving our community
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Forts Picolata, San Francisco de Pupo and Fort San Diego,
1739 - 1740
During 1739 - 1740 in addition to the Castillo de San Marcos, the lookout tower on the Matanzas Inlet, Fort Gracia Real de Santa Teresa de Mose (Fort Mose), and a lookout tower on Santa Anastasia Island as well as a few other places, there were three s
mall wooden forts, Fort Picolata, Fort San Francisco de Pupo, and Fort San Diego that were part of the Presidio de San Agustín defenses. All three where located to the north and west of the Castillo de San Marcos.
At Fort Mose Saturday, July 30, at 9:30 am, the Saint Augustine Garrison, National Park Service and Fort Mose State Park will conduct ceremonies to honor the Spanish soldiers (soldados Espanoles) who fought and died at the northern defense of St. Augustine.
This event is free and dedicated to better understanding of the history of Spanish La Florida.
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Spain's outposts 1739-1740
Fuerte San Francisco De Pupo (Fort Pupo)
In 1738 after an attack by the British-allied Yuchi Indians, the fort was enlarged to a 30-by-16 blockhouse, surrounded by a rampart of timber and earth. The road from St. Augustine to Tallahassee and Tampa Bay passed through the property and opened the shortest and best avenue from the river to the farming lands of Alachua.
Fort San Francisco de Pupo, according to General James Oglethorpe, was a strong new built tower about 30 foot high, 16 foot square, with a manchicolis above, which flanked the foot of the tower, without a rampart, faced with timber a foot thick and 12 foot high, filled up within each side with 6 foot earth.
Fuerte Picolata (Fort Picolata)
Fort Picolata was built and garrisoned by the Spanish to guard the river crossing at the ferry landing for the road they used to carry goods to and from Mission San Luis, near today's Tallahassee. The fort was built to protect the river crossing on that side of the river.
Located where the St. Johns River narrows, Fort Picolata provided San Agustín access to the Apalachee missions to the west and to points north and south along the river. In 1737 with Arredondo's recommendation Gov. Francisco del Moral Sanchez ordered the construction of a blockhouse, barracks, storehouses and batteries.
Spanish troops were quartered at fort Picolata for a month at a time, leaving their families in St. Augustine.
Fuerte San Diego (Fort San Diego)
In 1736 Diego de Espinosa owned a cattle ranch on Diego Plains, referred to as Fort San Diego, on a flat, open area. The fort of Diego de Espinosa was a square palisade with a fifteen foot wall and fortified, with two bastions at opposite corners, and armed with five guns, increased to 8 guns in 1740. It was usually manned by 16 soldados, 1 Sargento, and at least 1 allied Indian scout. The Fort was privately built by Don Diego de Espinosa.
During the English attack the fort had been reinforced with an additional 17 soldados (they were the replacements for the garrison already there). Captured by the British on May 23, 1740 and the entire garrison made prisoners of war.
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Note on dates
In all Spanish and English sources there are discrepancies in connection with the use of dates. This is due to the fact that the English in 1740 still remained on the Julian calendar, while the Spaniards used the modern Gregorian calendar which at that time was 11 days ahead of the old system.
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About 20 miles north of San Agustín was Fort San Diego, sitting amid cattle country called the Diego Plains. About 18 miles to the west of town, on the east side of the St. Johns, was Fort Picolata.
Together with Fort San Francisco de Pupo on the opposite side of the river, Fort Picolata guarded the important road path to the fort of Apalachee in Western Florida, where the Spaniards had a garrison; the two forts also blocked possible enemy movements by water up the St. Johns.
On December 24, 1739 La Florida Governor Don Manuel de Montiano, knowing of a possible English attack, held a council of war to decide whether it was advisable to demolish Fort Diego or reinforce it, and whether the Spanish forces were sufficiently strong to attack the enemy.
It was resolved to send a relief force of 17 men and various works of improvement were begun to secure the defense of the fort.
In the middle of December 1739 British forces numbering over a 1,000 men under the command of General James Oglethorpe began an invasion of Florida. On December 28, 1739 General Oglethorpe sent a force of over 200 British troops and Indian allies to take Fort Picolata. Although Fort Picolata was defended by just 7 soldados Espanoles and 1 Indian scout, they put up such a fierce defense that after about 5 hours the British forces retreated.
General Oglethorpe then took command and when he had a bulk of his forces he attacked Fort Picolata for a second time on or about January 7, 1740. This time there were at least 400 to 700 British troops and allied Indians and plenty of artillery. Fort Picolata fell shortly thereafter.
On or about January 8, 1740, the British attacked Fort San Francisco de Pupo. The Fort was defended by 13 soldados Espanoles and 1 Indian scout. The Fort defended itself for two days, but fell on or about January 9, 1740. From there the British forces made their way north to Fort San Diego and on or about May 21, 1740 surrounded the fort.
The British forces arrived near Fort San Diego about the middle of the night. They approached as near as they could and at daybreak of the 22nd the British attacked the fort and burned a house nearby, but the Spaniards fired so strongly upon them that they were obliged to retire.
However, at 10 o'clock in the morning General Oglethorpe came up with the whole body of troops about 400 - 700 men. He sent out his allied Indians to hunt for Spanish horses and cattle, and rode around to view the fort.
The Spaniards continued firing while the night fell, when the British surrounded the place with guards and sentries. Fort San Diego had a complement of about 35 soldados Espanoles in addition to the household of Don Diego de Espinoza for a total of about 50 people. The fort fell on or about May 23, 1740.
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The aftermath
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In a letter written on January 31, 1740 to Capitan General and Governor of Cuba (Habana) Don Juan Francisco de Guermes y Horcasitas La Florida Governor Don Manuel de Montiano states:
"I likewise invite Your Excellency's attention to the fact that the two aforementioned forts of Picolata and Pupo were constructed solely for the purpose of defending and sheltering from continual attack of Indian allies of the English, the mails that go to and come from Apalachee and that both were situated on the banks of the aforesaid San Juan (St. Johns), one on the north and the other to the south, at a distance of three-quarters of a league, the width of the river...
"In spite of being small and built of wood, they have defended themselves various times against Indians that have attacked them.
"Even now they of Picolata resisted four or five hours in spite of being invested by more than 200 men... The said Fort Pupo defended itself valiantly nearly two days..."
 In a second letter also sent to the capitan general and governor on June 11, 1740, Governor Montiano indicates the following concerning Fort San Diego: "Since then, I have learned in addition from a foreman of Espinosa's, that while his master and some other workmen were busy at San Diego on field works, 50 Indian allies of the English suddenly surrounded them, firing a volley into them and so killing one soldado and a negro of Espinosa's. "Nevertheless the others managed to get into the fort, except a Negro of the monastery of Saint Francis, who took to the woods... The Indians having failed to capture anyone withdrew. These things being so, I took the resolution of sending a Sargento and 12 men with a surgeon, to bring back the wounded, and if necessary, to leave some people as reinforcement, and then return. "The Sargento not having returned in two days, I sent a Cabo of cavalry with six men, to discover anything that might have occurred since in those parts. He returned the next day, saying that he was unable to reach the fort (Fort San Diego), the enemy by spreading out far and wide having given him no chance. ... "I have since learned by another scout, that they are strengthening the fort (Fort San Diego)... And others who frequently... say that their small parties are at a league from here, which makes me think they are present in force, and that they are establishing storehouses at San Diego for food and stores..."
Although the accounts from both sources, on the one side from General James Oglethorpe and on the other the letters and reports from Governor Montiano, seemingly have many contradictions as they usually do, based on all the primary sources researched as of this date, the above description of the events of the Presidio de San Agustín siege and defeat of all three forts are probably as close to what actually happened as we will get until and unless new documents are found in the Spanish archives.
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About this Special Report
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The information in this Special Report was drawn from a brochure prepared for the Ceremony to Honor the fallen Soldados Espanoles of Fort Picolata, Fort San Francisco de Pupo and Fort San Diego in the year of Our Lord 1740.
Reenactor/historian Orlando Ramirez researched the largely forgotten outposts of the San Agustin presidio and the fateful battles of 1739-1740,
Primary sources:
January to August 1740 Letters and reports of Governor Manuel de Montiano.
1740 Reports from General and Governor James Oglethorpe
Secondary sources: Priego Fernandez-Matos, Pedro, Manuel de Montiano y Sopelano. Cuadernos de la Escuela Diplomatica Numero 53. Ministerio de Asuntos Exteriores y de Cooperación, Madrid 2014. Goggin, John M.. Fort Pupo: A Spanish Frontier Outpost. Florida Historical Quarterly Vol. 30, Number 2, pp 139 - 192, 1951. Peres, Alonso; Cartografia de Ultramar Carpeta II: Estados Unidos y Canada, Laminas N' m. 50 y N' m. 64. Servicio Historico Militar, Madrid 1989. Map based on the description of both Spanish and British reports of the defenses of San Agustín in 1740,
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The St. Augustine Report is published weekly, with additional Reports previewing City Commission meetings as well as Special Reports. The Report is written and distributed by George Gardner, St. Augustine Mayor (2002-2006) and a former newspaper reporter and editor. Contact the Report at gardner@aug.com or gardnerstaug@yahoo.com
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