1589 A Third Attempt to Relieve the Roanoke Colonists

Illustration of the Spanish Armada by Granger.(1)

There are so many books about the Battle of the Spanish Armada that we will leave the description to them. Needless to say, the colonists at Roanoke were left to fend for themselves.

Walter Raleigh donated at least two of his ships to the war effort. Admiral Howard took command of the Bark Ralegh as his flagship, renaming her the Ark Royal. Ralegh also donated his pinnace, the Roebuck. But he did not see much action first hand. The Queen did not want her favorites on the front line of battle. He served as one of her war counselors along with his friends Richard Grenville, Ralph Lane, and Lord Grey. He also helped raise troops and kept busy improving the defenses in the ports of Devonshire and Cornwall.

The battle took place in the English Channel on August 8, 1588. As everyone knows, the English crushed the Spanish.

Ralegh’s activities afterward indicate that he was more interested in getting rich through privateering than in rescuing his Roanoke colonists. Records state that the Queen’s privy counsel reprimanded him when some of his ships captured two English ships by mistake; he claimed they were working for the Spanish. And the council put Ralegh on trial for taking two vessels from the friendly French.

When Walter got tired of dealing with the Privy Council and squabbling with the Earl of Essex, he headed back to Ireland to spend time at Youghal. Though his time there did not help his colonists in Virginia, it did help the local villagers. Ralegh planted potatoes, the first potatoes ever planted in Ireland. He planted Ireland’s first cherry trees, which he had imported from the Azores. He planted Ireland’s first tobacco, which he had imported from the West Indies. He also spent time writing a monumental poem about how he missed Queen Elizabeth. He gave it the disguised titled “The Ocean’s Love for Cynthia.” Hidden within the verse, he stated that his goals in life were “to seek new worlds for gold, for praise [and] for glory.”

Governor John White, on the other hand, would not let the matter of his abandoned daughter, grand-daughter, son-in-law, and friends rest. He was also living in Ireland, on land that Ralegh granted to him. In 1589, he encouraged Ralegh to seek investors and raise support for another rescue mission. On May 7, Ralegh, the Assistants of the City of Ralegh, and nineteen London merchant adventurers signed an agreement that founded a new company. The adventurers included Thomas Smythe of the Muscovy Company and William Sanderson, who had backed many of Ralegh’s previous adventures. Richard Hakluyt added his name to the list of supporters, as did an herbalist named John Gerard, a mathematician named Thomas Hood, and a merchant who would later become influential in the East India Company, Richard Wright.

In exchange for their financial backing of Virginia, the merchants were to receive free trade between Virginia and England for seven years. That meant they could carry on trade without paying any dues or taxes. The colonists and the Assistants were to receive free food, provisions, and shipping expenses. Ralegh was to pocket one fifth of any gold, silver, or other precious metals found. The crown would receive her fifth as well.

Unfortunately, this expedition never came about. Ralegh got distracted by other things, particularly a woman. Elizabeth Throckmorton was one of Queen Elizabeth’s handmaidens. Some historians believe she and Ralegh were secretly married as early as 1588.

White did not give up. But he could not gather the funds for an expedition to Roanoke all by himself. Luckily, in January of 1590, he saw an opportunity to deliver supplies to the island. He heard that a London merchant and successful privateer named John Watts was preparing a fleet of three heavily armed warships to sail to the West Indies. But the Queen’s Privy Council, upon hearing there might be another attempt by the Spanish to invade, ordered a stay on shipping. John White convinced Sir Ralegh to use his influence to persuade the Queen to allow Watts’ ships to proceed if, and only if, they dropped White and his supplies at Roanoke on their way. Master Watts agreed to Sir Ralegh’s deal, and the Queen’s Council gave Watts the allowance he needed. Again, we will let Governor White tell you what happened.

“I was too easily out maneuvered. When it came time to arrange for the provisions I needed for my plantation, Master Watts would allow nothing on his ship save my self and my chest.

His two ships, the Hopewell and the Moonlight, departed on the twentieth day of March. I was a passenger on the Hopewell [a ship that will make another appearance in the story about the Pilgrims in Section 4]. It was a long trip. We did not sight Virginia until five months later, on August 15. As we neared the outer banks protecting the sound where Roanoke Island lay, we saw a great smoke. I thought it to be my comrades having a friendly fire.

John White’s map of Pamlico Sound, Albemarle Sound, and Roanoke Island 1585 or 1586.(2)

“The next morning, Captain Abraham Cocke of the Hopewell, and Captain Edward Spicer of the Moonlight, prepared to take me ashore in their long boats. The Hopewell and Moonlight were harbored in the breach [break] between the two islands of the outer banks. As the long boats departed, the captains commanded the master gunner to make ready [get ready to fire] two minions and a falcon to shoot them off with reasonable space [time] between every shot, to the end [with the result] that their reports [sounds] might be heard at the place where we hoped to find some of our people.

“Our boats passed through the breach and headed toward the beach of the mainland. The boson took soundings along the way to negotiate the numerous shoals within the sound. To my surprise and confusion, halfway between the ships and the shore, we saw another great smoke to the southwest of Kendrick’s Mounts [sand dunes that used to exist between current day Rodanthe and Salvo.](3) I decided the plantation had moved, as we had agreed before I left they would, so it would be better to check out the second smoke first. Our men rowed very hard against the currents. It was a long way, and we all arrived tired and thirsty. When we came to the smoke we were greatly grieved to find no man nor sign that any had been there lately, nor was there any fresh water after all that way to drink. Being thus wearied with this journey, we returned to the harbor where we left our boats.

“Roanoke was some twenty miles north of where we were anchored. By the next morning, the weather, already foul, turned nasty as a great gale from the northeast sent breakers crashing on our tiny harbor. Having run dry of fresh water, Captain Spicer ordered the barrels refilled before we could leave. In spite of the tumultuous sea, the Hopewell was able to deliver me to land. But as we watched the Moonlight enter the breach, a very dangerous sea broke onto the boat and overset them quite. The men kept to the boat, some in it and some hanging on it, but the next large wave set the boat aground.

“Some of the crew kept hold of the ship, including Captain Spicer and his mate Ralph Skinner, hoping they could eventually wade to shore. But the sea still beat them down so that they could neither stand nor swim and the boat twice or thrice was turned the keel upward [upside down].

“Eleven men, including Captain Spicer and Skinner, flailed in the deep water. I am unable to swim. But Captain Cocke, seeing the Moonlight overturned, stripped and, with four good swimmers, swam to their rescue. They were only able to save four. Captain Spicer and Skinner hung on until they sunk and were seen no more.

“[Yet, even after watching seven of his best seamen drown,] Master Cocke was willing to proceed to deliver me to Roanoke. Nineteen seamen remained with us. Captain John Bedford took over the command of the Moonlight, which was uprighted and refitted, while the ship’s carpenter repaired the Hopewell. Refreshed, we sailed back into the sound towards my plantation.

“Night descended before we reached the island, so we nearly passed it by mistake. Then, just as we came to the north end, we saw another great smoke. This time I was sure it was my party signaling to me. It being too late in the day to pull ashore, we anchored nearby. As we waited out the night, we sounded with a trumpet call, and sang many familiar English tunes of songs, calling to the planters in a friendly manner. But we had no answer.

“At first dawn we launched the long boats and rowed directly to shore. [I had noted in my journal the night before that] it was just ten days short of three years since I left my beloved family and friends on Roanoke. As my boat hit the sand, I bounded from it and ran towards the place where I had seen the smoke. But instead of a camp fire, I found only grass and sundry rotten trees burning about the place from lightning that had struck the night before.

“I demanded the men do a thorough search of the place. Leaving the boats on the northeast coast, we walked south across the island to the west side. We were just across the channel from the Indian village of Dasemunkepeuc, but we saw no smoke coming from that direction. After finding no evidence of occupation, we retraced our steps along the northern coastline until we came to the place where I left our colony in the year 1585.

“In all this way, the only sign of humanity were two or three sorts of footprints in the sand of the savage’s feet trodden that night. Then, as we entered up the sandy bank, I saw upon a tree in the very brow thereof, curiously carved, the fair [clear] Roman letters C-R-O [for Croatoan]. Presently, we knew these letters signified the place where I should find the planters seated [in residence] according to a secret token [sign] agreed between them and me at my last departure from them. The agreement was that they [the colonists] should not fail to write or carve on the trees or posts of the doors the name of the place where they should be seated, for at my coming away they were prepared to remove to Roanoke fifty miles into the maine. [‘Maine’ probably meant inland toward Manteo’s tribe to avoid detection by the Spanish and hostile Roanoke Indians].

“At my departure from them in Anno 1587, I willed [asked] them that if they should happen to be distressed in any of those places, that then they should carve a cross over the letters or name. Since we found no such sign of distress, I believed my people willingly and peacefully moved to Manteo’s Croatoan Village on the mainland. Comforted by this sign, our party walked on to the place on the island where the village had been when I left it.

“We passed to the place where they were left in sundry [various] houses. But we found the houses taken down. The place was very strongly enclosed with a high palisade [pillared wall or fortress] of great trees, with curtains and flankers very fort-like. One of the chief trees or posts at the right side of the entrance had the bark stripped off. In the place where the bark was stripped off, five feet from the ground, was graven [engraved] in fair capital letters the word CROATOAN. To my relief, it was without any cross or sign of distress.

“We entered into the palisade where we found many bars of iron, two pigs of lead, four iron fowlers [small guns], iron saker-shot, and such like heavy things, thrown here and there, almost overgrown with grass and weeds. From thence [there] we went along by the waterside, toward the point of the creek, to see if we could find any of their boats or pinnaces. But we could perceive no sign of them, nor any of the last falcons [small guns] or small ordnance which were left with them.

“At our return from the creek, some of our sailors, meeting us, told us that they had found where divers [an assortment of] chests had been hidden. The chests had long since been dug up again and broken up, probably by the Roanokes, and much of the goods in them was spoiled and scattered about. Nothing was left of such things as the savages knew any use of undefaced [not ruined].

“Presently, Captain Cocke and I went to the end of an old trench, made two years past [ago] by Captain Amadas, where we found five more chests that had been carefully hidden by the planters. Of [among] those same chests were my own, and about the place many of my things were spoiled and broken. My books had their covers torn from them. The frames of some of my pictures and maps were rotten and spoiled by the rain. And my armor was almost eaten through with rust. This could be no other but the deed of the savages, our enemies at Dasemunkepeuc, who had watched the departure of our men to Croatoan. As soon as they had departed, the savages dug up every place where they suspected anything to be buried, [took what they wanted, and spoiled the rest].

“Although it grieved me to see such spoil [ruin] of my goods, yet on the other side [on the other hand], I greatly joyed that I had safely found a certain token of their safe being at Croatoan, which is the place where Manteo was born. The savages of the island [Croatoan Island, today’s Hattaras] were our friends.

“When we had seen in this place so much as we could, we returned to our boats and departed from the shore toward our ships with as much speed as we could, for the weather began to overcast, and very likely that a foul and stormy night would ensue [begin].

Tracing of John White’s map shown above.

Captain Cocke agreed to take me to the Croatoan village [historians quibble whether White meant the village at Dasemunkepeuc or Manteo’s mother village on the barrier reef that White labeled Croatoan on the map above]. But the storm lasted several days. On the third day, our two vessels set out, losing two anchors and some cables in the process. The weather grew fouler and fouler, and our victuals scarce and our cask and fresh water lost. Master Cocke finally gave up the quest. He proposed that we spend the winter months among the warmer West Indian islands [where he could do a little pirating]. He promised we would return to look for my people in the spring.

Master Bedford was not in favor of this plan. Desiring to go home, he set the Moonlight’s course for England, while Master Cocke pointed our Hopewell for Trinidad. To my distress, Cocke changed his mind along the way and turned us toward the Azores. To add further grief, after chasing several Spanish ships without success, he, too, turned for home. We entered Plymouth Harbour on October 24. I had been away from England for seven months.”

Governor White returned to his rented lands in Ireland on Ralegh’s estate at Youghal until he could find another way to return to Roanoke. Historians have yet to find any more records of his returning to Roanoke to search for his daughter, son-in-law, granddaughter and the rest of the colonists.

Much later, in July of 1603, Sir Ralegh will send Bartholomew Gilbert, about whom we shall hear presently, to the Chesapeake to look for the colonists. Gilbert and four crewmen went to shore where they ran afoul of a band of Algonquian Indians who killed them on July 29. The rest of Gilbert’s crew returned to England.

In 1607, when the first planters sail to Virginia to found Jamestowne, they will be given the mission to search for the colonists, as you shall see. But no one will ever find them.

Next article: Theories About What Happened to the Roanoke Colonists


  1. Cropped painting of the Spanish Armada by Granger. {{PD-Old}} Public Domain. Image source url.: http://images.fineartamerica.com/images-medium-large/14-spanish-armada-1588-granger.jpg
  2. John White’s map of Roanoke. 1585 or 1586{{PD-Old}} Public Domain. Image source url: https://nativeheritageproject.files.wordpress.com/2012/05/fort-large-map1.png
  3. Shirley’s footnote to page 68.