Of these out-posts, there were two, one on each side of the river St. Johns—at Picolata and immediately opposite—and at Diego. The purpose of the forts at Picolata was to guard the passage of the river, and to keep open the communication with St. Marks and Pensacola; and when threatened with the invasion of Oglethorpe, messengers were dispatched to the governor of Pensacola for aid, and also to Mexico by the same route. The fort at Diego was but a small work, erected by Don Diego de Spinosa, upon his own estate; and the remains of it, with one or two cannon, are still visible. Fort Moosa, was an out-post at the place now known by that name, on the North River, about two miles north of St. Augustine. A fortified line, a considerable portion of which may now be traced, extended across from the stockades on the St. Sebastian to Fort Moosa. Communication by a tide-creek existed through the marshes, between the castle at St. Augustine and Fort Moosa.

Oglethorpe first attacked the two forts at Picolata, one of which, called Fort Poppa, or St. Francis de Poppa, was a place of some strength. Its remains still exist, about one-fourth of a mile north of the termination of the Bellamy Road, its earthworks being still strongly marked.

After a slight resistance, both forts fell into his hands, much to the annoyance of Governor Monteano. Oglethorpe speaks of Fort Francis as being of much importance, "as commanding the passes from St. Augustine to Mexico, and into the country of the Creek Indians, and also being upon the ferry, where the troops which come from St. Augustine must pass." He found in it, one mortar piece, two carriages, three small guns, ammunition, one hundred and fifty shells, and fifty glass bottles full of gunpowder, with fuses—a somewhat novel missile of war.

The English general's plan of operation was, that the crews and troops upon the vessels should land, and throw up batteries upon Anastasia Island, from thence bombarding the town; while he himself designed to lead the attack on the land side. Having arrived in position, he gave the signal of attack to the fleet, by sending up a rocket; but no response came from the vessels, and he had the mortification of being obliged to withdraw his troops. The troops were unable to effect a landing from the vessels, in consequence of a number of armed Spanish galleys having been drawn up inside the bar; so that no landing could be made except under a severe fire, while the galleys were protected from an attack by the ships, in consequence of the shoal water.

He then prepared to reduce the town by a regular siege, with a strict blockade by sea. He hoped, by driving the inhabitants into the castle, so to encumber the governor with useless mouths, as to reduce him to the necessity of a surrender, to avoid starvation. The town was placed under the range of his heavy artillery and mortars, and soon became untenable, forcing the citizens generally to seek the shelter of the fort.

Col. Vanderduysen was posted at Point Quartel; and others of the troops upon Anastasia Island, and the north beach. Three batteries were erected: one on Anastasia Island, called the Poza, which consisted of four eighteen-pounders and one nine-pounder; one on the point of the wood of the island, mounting two eighteen-pounders. The remains of the Peza battery are still to be seen, almost as distinctly marked as on the day of its creation. Four mortars and forty cohorns were employed in the siege.

The siege began on the 12th June; and on the 25th June a night sortie was made from the castle against a portion of the troops under command of Col. Palmer, who were encamped at Fort Moosa, including a company of Scotch Highlanders, numbering eighty-five men, under their chief, Capt. McIntosh, all equipped in Highland dress. This attack was entirely successful, and the English sustained a severe loss, their colonel being killed, with twenty Highlanders, twenty-seven soldiers, and a number of Indians.

This affair at Fort Moosa has generally been considered as a surprise, and its disastrous results as the consequence of carelessness and disobedience of the orders of Oglethorpe. Captain McIntosh, the leader of the Highlanders, was taken prisoner, and finally transferred to Spain. From his prison at St. Sebastian, under date of 20th June, 1741, he gives the following account of the matter:—

"I listed seventy men, all in Highland dress, and marched to the siege, and was ordered to scout nigh St. Augustine and molest the enemy, while the general and the rest of his little army went to an island where we could have no succor of them. I punctually obeyed my orders, until seven hundred Spaniards sallied out from the garrison, an hour before daylight. They did not surprise us, for we were all under arms, ready to receive them, which we did briskly, keeping a constant firing for a quarter of an hour, when they prest on with numbers; was obliged to take our swords until the most of us were shot and cut to pieces. You are to observe we had but eighty men; and the engagement was in view of the rest of our army, but they could not come to our assistance, by being in the foresaid island, under the enemy's guns. They had twenty prisoners, a few got off, the rest killed; as we were well informed by some of themselves, they had three hundred killed on the spot,[29] besides several wounded. We were all stripped naked of clothes, brought to St. Augustine, where we remained three months in close confinement."[30]

This officer was Capt. John McIntosh; and his son, Brig. Gen. McIntosh, then a youth of fourteen, was present in the engagement, and escaped without injury. The family of the McIntoshes have always been conspicuous in the history of Georgia.