1587 Ralegh’s Second Attempt to Plant a Colony on Roanoke

While Sir Richard Grenville and Ralph Lane struggled to establish Roanoke, and Thomas Cavendish circled the globe in Desire, Sir Walter Ralegh dealt with some difficulties on the personal front. In 1587, Robert Devereaux, the 2nd Earl of Essex, entered Queen Elizabeth’s court. This charming, exceedingly handsome twenty-year-old captured the eye of the Queen the moment he entered her presence. Elizabeth was fifty-four, almost three times Essex’s senior. Nonetheless, he was soon “at cards, or one game or another with her till the birds sing in the morning.”

The Queen’s new suitor was a jealous man. He tried to rid the court of Ralegh. But the Queen saw no reason to choose between her courtiers. She would have as many favorites as she desired. However, Essex’s presence diluted the Queen’s time, releasing her hold on Ralegh, somewhat. Ralegh would be able to spend more time on his colonization projects both in America and in Ireland.

One of Ralegh’s tasks was to take possession of his Irish lands, particularly his new 12,000 acre estate in the barony of Imokilly between Lismore and today’s Castlemartyr. That included the Norman castle of ‘Castlemartyr’, referred to then as ‘Ballymartyr’, which is an anglicized version of the Irish ‘Baile na Martra’. Castlemartyr was/is about four miles west of Youghal. During the period between the two Desmond Rebellions, Sir Henry Sidney, Lord Deputy of Ireland had captured Ballymartyr. The castle was the headquarters of the Geraldine seneschal John FitzEdmund FitzGerald. It had been in the FitzGerald family since the lands were granted to them during the Norman Conquest.

Today, ruins of John FitzEdmund FitzGerald’s castle form part of the enclosure of the POSH(1) Castlymartyr hotel in Castlemartyr.(2)

During the Second Desmond Rebellion, John FitzEdmund and his Madraí na Fola [Dogs of Blood] took Ballymartyr back again. But near the end of the rebellion, Thomas Butler, the Earl of Ormond overran Imokilly and recaptured the castle. As part of his own personal vendetta, Ormond abducted John FitzEdmund’s elderly mother and hung her from the castle wall. Deflated, John FitzEdmund submitted to the Earl, hoping for his freedom. But the English arrested him again in 1585. He died in Dublin prison in 1586. By that time, the Queen had given Ballymartyr to Ralegh.

Sir Henry Sidney placed Sir Ralegh as the new mayor of Youghal. At some point, Sir Richard Grenville, Ralph Lane, and Thomas Harriot were granted estates nearby. John White, who was not as wealthy as the others, will rent a place on Ralegh’s estate.

When Ralph Lane, John White, and Thomas Harriot returned from Roanoke, Ralegh was in residence in Youghal. Harriot and White traveled to Ballymartyr to deliver Ralph Lane’s report on the colony. White supplemented the report with his exquisite illustrations. Harriot provided his reports on the flora and fauna.

Ralph Lane had explored much of the area around Roanoke. He had surveyed as far south as the Secoton village between today’s Pamlico and Neuse Rivers and 130 miles north to the “country of the Chesapian” Indians [after whom the Chesapeake was named]. In his report, Lane insisted that the City of Ralegh would be better positioned on the Chesapeake Bay rather than at Roanoke. The Chesapeake Bay had deeper, more protected harbors, and – so Lane had been told – there was “an abundance of gold, silver, and pearls” there.

White and Harriot supported Lane’s position on moving the colony. However, they did not think Lane was the best man for the leadership role. They criticized Lane for not encouraging the colony to be self-sustaining, and for his harsh and cruel treatment of the Roanoke Indians. They suggested that the next group of colonists should be chosen by their willingness to work the land. “Planters should live in harmony with their native neighbors,” they insisted, “and show the natives the English Christian culture through good example, not through force like the Spanish were enforcing Catholicism.”

With all these suggestions in mind, on January 7, 1587, Ralegh and his associates founded a new company. They referred to it as the “Governor and Assistants of the City of Ralegh in Virginia” and chose John White to serve as the company’s governor. They elected twelve men to serve on the Board of Assistants(3) including Ananias Dare [who was married to John White’s daughter, Eleanor] and Simon Fernandez [Ralegh’s and Grenville’s pilot and fellow pirate]. All twelve assistants were “of London.” All but three were to accompany White on the next expedition.

Funds came forth easily. Once again, William Sanderson recruited generous London investors and added his own money to the pot. Queen Elizabeth gave Raleigh, on March 17, 1587, the forfeited lands of the executed traitor, Anthony Babington [of the Babington Plot], which added money to Ralegh’s purse.

The next step was to recruit planters. Settlers who paid their own way by investing were offered a minimum of 500 acres of land if they promised to work it. 115 people elected to participate. 16 of them were women – a first for English colonization. Board of Assistant member Ananias Dare planned to take Eleanor, who was pregnant – another first. Assistant Dionysus Harvey was taking his wife, Marjory, who was also pregnant

John White kept a journal of the expedition, which we interpret below:

“On the sixth and twentieth of April, a fleet of three sails, including the Admiral [the Lyon], a ship of 120 tons, a flyboat, and a pinnace, departed from Portsmouth. That same day we came to anchor at the Cowes in the Isle of Wight, where we stayed for eight days waiting for favorable weather. We made a second two-day stop in Plymouth before heading through the open sea for Virginia. On the sixteenth of May, Simon Fernandez, Master of the Lyon [more interested in pirating than in settling a colony in America], lewdly forsook our flyboat, leaving her distressed in the Bay of Portugal [Lisbon].

[Simon Fernandez and] the flyboat caught up with us two days after we reached Dominica. The trip had taken the Lyon and the pinnace forty-two days from Plymouth – a speedy crossing.

[On] July 22, I desired to stop at Roanoke to check in on the fifteen men left there [by Sir Grenville] and then proceed to the Chesapeake. Ralegh’s written instructions demanded that the new colony should make its seat and fort there.

Master Simon Fernandez, who had been part of the earlier voyages, had another design [plan] and [would not follow my authority]. As soon as I put out in the pinnace for Roanoke, carrying forty of my best men to look for Grenville’s men, Fernandez called to the crew sailing the pinnace to leave us on the island [and not take us to the Chesapeake]. Only I and two or three of my men were to be brought back to the ship to fetch the others. “The summer is spent,” claimed Fernandez, “and I will land the planters in no other place.”

With that, he headed back to the Azores knowing that in late August or early September the Spanish fleets were due to pass through.

We were left stranded on Roanoke with no way to move north. When we came thither [to Roanoke Island], we found the fort razed down, but all the houses standing unhurt, saving [except] the lower rooms, which, with the fort, were overgrown with melons of divers sorts. We found deer within them, feeding on the melons. We returned to our company without hope of ever seeing any of the fifteen men living.”

Governor White’s party found the bones of one of the men the Indians had slain “long ago.” They did not yet know about the battle between Governor Lane and the Indians when Lane’s men killed Pemisapan.

In search of Grenville’s men, the English traveled to Croatoan [Hattaras], which was inhabited by Manteo’s mother and her kindred “who were ever friendly.” Manteo’s mother served as the sachem [leader]. Remember, heredity passed through the women. There the English learned the fate of the men left on Roanoke the year before:

Manteo’s mother and the Croatoans told White that Grenville’s men went to live in the houses left by Lane’s party, but “carelessly and off their guard.” One day, a company of Secotan and Aquasogoc Indians from the mainland came out suddenly from the woods upon the houses. The Indians killed one English in a parley and drove the rest into a house and set fire to it. The English fought their way out to the waterside, piled into their boat, and retreated to “a little island on the right hand of an entrance into the harbor of Hatorask [Hattaras], where they remained a while, but afterwards departed, wither as yet we know not.”

The Croatoans told Governor White that the Roanoke Indians had moved from the island to the mainland. But they were unable to tell the governor what had transpired while Lane was in charge, that Wanchese had taken over as sachem of the Roanokes, and that he had allied with the Secotan and Aquasogoc Indians from the mainland and become an enemy of the English.

Since White had no way to transport his colony to the Chesapeake to follow Ralegh’s orders, the new planters set about rebuilding the settlement at the northern end of Roanoke Island. White did not know how much danger he was placing his colonists in.

Roanoke Museum, Roanoke Island, Dare County, North Carolina, 2010.

During the first week, George Howe, one of the nine Assistants, left the compound to capture crabs on the beach. He was alone and not wearing his protective armor. Some of Wanchese’s tribe were on Roanoke for the day hunting for deer. When they saw Howe, they attacked, pelting him with arrows that “wounded him sixteen times.” Then they “slayed him with their wooden swords and beat his head to pieces.”

Governor White did not understand why the Roanokes had become so hostile. He went in search of Manteo, who had resumed his position as sachem of another Croatoan tribe in the village of Dasemonquepeuk on the mainland. Manteo had a lot of influence in the area, especially since he was allied with his mother, the sachem of the Croatoan village on Hatteras Island. White asked Manteo to find out why the Roanokes had killed Howe.

Manteo called a meeting in Dasemonquepeuk with Wanchese and the neighboring Weroan Indian villages of Pomiock, Secotan, and Aquascogoc. He learned about Lane killing King Pemisapan. The Roanokes had retaliated by killing not just Howe, but also Grenville’s fifteen men.

Governor White was deeply distressed to hear Manteo’s report. Since the Roanokes had become enemies of the English, they would no longer trade or negotiate with his colony. In response, he made the first of two huge mistakes. In the early hours of dawn, he dispatched a small army of twenty-four soldiers under a Captain Stafford to attack Dasemonquepeuk, thinking the village was filled with Roanoke refugees. English soldiers shot one of the male Indians before learning the resident Indians were Croatoan families of Manteo’s tribe, not Wanchese’s Roanoke Indians. The Roanokes had abandoned their fields and the Croatoan Indians had come to harvest the crops.

Four days later, on August 13, in an effort to keep Manteo on their side, the colony baptized him and honored him with the title “Lord of Dasemonkepeuc[sic]”(4) for trying to bring peace between the English and the Croatoans. [There must have been an Anglican priest among the English to perform the sacrament of baptism.]

Five days after that, on August 18, Eleanor Dare, Governor White’s daughter, “was delivered of a daughter.” Her parents and grandfather christened the baby the following Sunday as Virginia Dare, the first Christian born in Virginia.

Memorial to Virginia Dare on Roanoke Island in 2010.

Then Governor White made the second major mistake. This one much graver than the first. We will let him tell you about it himself.

By this time [the planters had been in America for thirty-four days] our ships had unlanded the goods and victuals of the planters, and began to take in wood and fresh water, and to calk and trim them for England. The planters also prepared their letters and tokens to send back [with the ship]. I wanted two of my assistants to return with the ship to ensure that the proper supplies were procured back in England. But none of the assistants would leave his family, or his newly acquired land. They all insisted that I go myself.

Afraid my property would be lost while I was away, I drafted a document [dated August 25, 1587(5)] guarantying that my assistants would restore my property if any of it got lost while I was away. On August 27, just a week after witnessing the christening of my granddaughter, I boarded the flyboat with fourteen other men bound for England.

Captain Fernandez [who had returned] ordered the anchor weighed. As the crew pushed the capstan bars around, one of them broke and flew through the air injuring twelve good men. Our flyboat departed [anyway], and we eventually reached the Azores. There, Captain Fernandez refused to continue on. [He wanted to, once again, seek Spanish prizes], leaving me and the injured crew to carry on without him. Six days later we ran into a gale that pushed us off course. We were already short of the needed food and water to reach land. Some on board were barely alive when our vessel finally landed on a shore.

At first we knew not what land it was. Eventually it came to light we were at Smerwick(6) on the west coast of Ireland. I obtained fresh fruit and water for my famished crew, but the boatswain and his mate died just the same. Some local residents and I moved the rest ashore, then I left for London. When I arrived, I found that Fernandez had arrived on the Lyon three weeks prior. He had not obtained any prizes and his crew was so ill that every man among them had to be carried on to shore.

Governor White met with Sir Ralegh on November 20, apparently in London, when the city was bustling with news that King Philip and his Catholic allies were about to invade. Philip wanted to rid England of her Protestant monarchy, and return the country to Catholicism once and for all.

King Philip was in command of the two most powerful navies in Europe: the Portuguese and Spanish. English mariners were certainly intimidated. They stepped up their privateering efforts in order to weaken the armada by stealing Spain’s ships. They could also weaken the empire’s purse by stealing her Aztec and Inca treasure.

King Philip moved next by confiscating all British ships in Spanish ports. He imprisoned their crews and combined the British ships with his own navies, which were preparing to attack England soon. “A tall ship of London” that had been among the ships confiscated by the king, managed to escape from Cadiz and alert Queen Elizabeth of Philip’s plans. Elizabeth officially declared war on Spain and attacked first.

Sir Francis Drake, with a fleet of twelve warships, sailed to the port of Cadiz(7), the home port of the Spanish navy. Cadiz is a very large harbor on the southwestern coast of Spain on the Atlantic. Drake planned to destroy every last ship before it could leave port to attack England. Shooting, burning, and looting at will, the English sank, burned, or captured thirty-seven vessels. Then Drake prowled the coastline around Cadiz attacking and pirating Spanish supply and treasure ships out of port.

After a few weeks of that, he learned that the carrack San Philipe, laden with a cargo valued at £114,000, was on its way to the Azores. He reached the archipelago in time to capture the Spanish prize, the loot from which paid for the raid on Cadiz. ‘El Drago’, as Philip called him, arrived home claiming he had “singed the King of Spain’s beard.”

In truth, Sir Drake had only delayed the battle with the Spanish Armada by one year. By the time Governor White delivered his report to Sir Ralegh, Queen Elizabeth and her people were too distracted by King Philip to think about the tiny colony in far off Virginia. The Privy Council had already issued a decree stating that every boat, ship, and floating device would be needed to combat the Armada.

Ignoring the council’s decree, Ralegh, White, and Richard Grenville proceeded with plans to relieve the Roanoke colonists. By February, 1588 [the Armada will attack in August], White had outfitted two small vessels. A 30-ton bark called the Brave under the command of Arthur Facy was to carry seven men and two women. Pedro Diaz would serve as the pilot. Ralegh’s 25-ton Roebuck [aka Roe], was to carry more colonists. Both vessels were filled with provisions including meat, vegetables, and biscuits.

Grenville provided five more vessels: the Dudley, a 250-ton galleon; the Virgin-God Save Her of 200-tons; his former flagship, the Tiger; Humphrey Gilbert’s old Golden Hind; and the St. Leger [owned by Grenville’s in-laws]. Grenville’s fleet was ready and waiting on the Thames when, on March 32, the Privy Council learned about the venture and confiscated the ships. “In Her Majesty’s name and upon his allegiance, [Grenville was] to forbear to go on his intended voyage, and to have the ships so by him prepared to be in readiness to join with Her Majesty’s navy as he shall be directed hereafter.” Grenville turned over his ships to Sir Drake in Plymouth Harbour.

However, Grenville was allowed to “dispose of and employ” his smaller vessels as he saw fit. The 30-ton Brave and 20-ton Roe were free to sail to America. Governor White described what happened:

On April 22, 1588, I departed from Bideford [Grenville’s port], in two pinnaces [the Brave and the Roebuck] with fifteen planters and some necessary provisions. No sooner were we off the coast of England when [Captain] Facy, who had previously worked for Grenville, turned the ships to privateering. Still in sight of land, the Brave chased four ships and searched them for loot. The following day our seamen boarded two more ships – one a Scot and the other a Breton – and Facy took from them whatsoever he could find worth the taking, and so let them go.(8)

On April 29, the Roe attacked a hulk of 200 tons and more.

On May 5, near the island of Madeira, the two pinnaces encountered a pair of French men-of-war, well manned and bravely bound for Peru. The weather prevented flight, so the Brave prepared to defend herself. As the French approached at two of the clock in the afternoon, the Brave hailed the ships in a friendly manner. The French did not answer. Instead, they prepared for battle by showing their broadside. The Brave fired and blasted the shoulder from their master gunner. Men on both sides boarded each other’s boats with swords and pistols in hand. The fight went on for one and a half hours with some twenty-three men slain. The surviving leaders were wounded in six to twelve places.

Our master on the Brave and his mate were mortally wounded and bedridden. I was wounded twice in the head – once with a sword and once with a spike – and also hurt with a shot in my buttock. Master Diaz had a pike scraped across his face then thrust quite through the head. The colonists, who were also receiving wounds, got in the way of the fighting soldiers and crew, who had finally spent their ammunition. Whereupon, the French cut down the netting over the deck meant to stave off arrows. The French then flooded the ship with as many men as could fit on the poop and forecastle decks.

From there they played extremely upon the Brave’s passengers with their shot. As they resolved to die fighting, the captain of the French ship asked them to yield [surrender]. However, after they did yield, the French realized how many of their own they had lost and went into another mad fury and began attacking our soldiers again. Finally the French captain charged [ordered] them to stop. Once pacified, they went about rifling through the Brave and carrying the goods on board their own ship which took all day and until four of the clock the next day.

The French robbed the Brave of our food, powder, weapons and provisions, leaving my ship not at their departing any thing worth the carrying away. Being thus ransacked, my party determined to return to England. With nothing but some biscuits to eat, the few able and unhurt men set about repairing the rigging and mending the sails.

On May 22, the Brave hobbled into Bideford port in Cornwall, followed by the Roe[buck] a few weeks later. We did not perform our intended voyage for the relief of the planters in Virginia, which thereby were not a little distressed.

Since John White was ranked an officer in her Majesty’s Navy, it was not long before he, too, had to answer the Queen’s call to fight. He will have to forsake his efforts to rescue his friends and family in faraway Roanoke until the battle against the Spanish is over.

Next article: 1589 Governor White Makes Another Attempt to Relieve the Roanoke Colonists


  1. Portside Out, Starboard Home – the desired views from the first class cabins on old cruise lines.
  2. The website video on Castlemartyr stated that more than 90 percent of the residents are “happy villagers.”
  3. The Board of Assistants were: Robert Bailey, Ananias Dare (John White’s son-in-law), Christopher Cooper, Simon Fernandez (the pilot), William Fullwood, Dionysus Harvey, George Howe, John Nichols, James Platt, Roger Pratt, John Sampson and Thomas Stevens
  4. Estes, Roberta. Where Have All the Indians Gone? Native American Eastern Seaboard Dispersal, Genealogy and DNA in Relation to Sir Walter Raleigh’s Lost Colony of Roanoke. Journal of Genetic Genealogy, 5(2):96-130. 2009
  5. The document still exists today.
  6. You probably recognize Smerwick. It is where Ralegh and his fellow soldiers slaughtered 600 Irish, Italian and Biscay Catholics during the Second Desmond Rebellion.
  7. We talked about Cadiz in Crossing the Ocean Sea. It was one of the first ports created on the Iberian peninsula by the Phoenicians. Even today, natives of Cadiz are very proud of their Phoenician heritage.
  8. Shirley, p. 59