Roanoke Colony

The Roanoke Colony ( ) refers to two attempts by Sir Walter Raleigh to found the first permanent English settlement in North America. The first colony was established at Roanoke Island in 1585 as a military outpost, and was evacuated in 1586. The more famous second colony, known as the Lost Colony, began when a new group of settlers under John White arrived on the island in 1587; a relief ship in 1590 found the colony mysteriously abandoned. The fate of the 112 to 121 colonists remains unknown.

Roanoke Colony was founded by Governor Ralph Lane in 1585 on Roanoke Island in present-day Dare County, North Carolina. Lane's colony was troubled by a lack of supplies and poor relations with some of the local Indian tribes. A resupply mission by Sir Richard Grenville was delayed, so Lane abandoned the colony and returned to England with Sir Francis Drake in 1586. Grenville arrived two weeks later and also returned home, leaving behind a small detachment to protect Raleigh's claim. A second expedition led by John White landed on the island in 1587. Sir Walter Raleigh had sent him to establish the "Cittie of Raleigh" on the Chesapeake Bay.

During a stop to check on Grenville's men, ship's pilot Simon Fernandes forced White and his colonists to remain on Roanoke. White returned to England with Fernandes, intending to bring more supplies in 1588. The Anglo-Spanish War delayed his return to Roanoke until 1590, and he found the settlement fortified but abandoned. The cryptic word "CROATOAN" was found carved into the palisade, which White interpreted to mean that the colonists had relocated to Croatoan Island. Before he could follow this lead, rough seas and a lost anchor forced the mission to return to England. That attempt became known as the "Lost Colony".

Speculation that the colonists had assimilated with nearby Indian tribes appears in writings as early as 1605. Investigations by the Jamestown colonists produced reports that the Roanoke settlers had been massacred, and there were stories of people with European features being seen in Indian villages, but no conclusive evidence was found. Interest in the matter fell until 1834, when George Bancroft published his account in ''A History of the United States''. Bancroft's description of the colonists cast them as foundational figures in American culture, particularly White's infant granddaughter Virginia Dare, and it captured the public imagination.

Background

The Outer Banks were explored in 1524 by Giovanni da Verrazzano, who mistook Pamlico Sound for the Pacific Ocean, and concluded that the barrier islands were an isthmus. Recognizing this as a potential shortcut to China, he presented his findings to King Francis I of France and King Henry VIII of England, neither of whom pursued the matter.

In 1578, Queen Elizabeth I granted a charter to Sir Humphrey Gilbert to explore and colonize territories "unclaimed by Christian kingdoms". Gilbert had helped to crush the first of the Desmond Rebellions in Ireland's Munster province in the early 1570s. The terms of the charter granted by the Queen were vague, although Gilbert understood it to give him rights to all territory in the New World north of Spanish Florida. Led by Gilbert, the English briefly claimed St. John's, Newfoundland, in 1583, as the first English territory in North America at the royal prerogative of Queen Elizabeth I, but Gilbert was lost at sea on his return journey to England.

Following Gilbert's death in 1583, Queen Elizabeth divided the charter between his brother Adrian Gilbert, and his half-brother Sir Walter Raleigh. Adrian's charter gave him the patent on Newfoundland and all points north, where geographers expected to eventually find a long-sought Northwest Passage to Asia. Raleigh was awarded the lands to the south, though much of it was already claimed by Spain. Richard Hakluyt, however, had by this time taken notice of Verazzano's "isthmus" – located within Raleigh's claim – and was campaigning for England to capitalize on the opportunity.

Raleigh's charter, issued on March 25, 1584, specified that he needed to establish a colony by 1591, or lose his right to colonization. He was to "discover, search, find out, and view such remote heathen and barbarous Lands, Countries, and territories ... to have, hold, occupy, and enjoy". It was expected that Raleigh would establish a base from which to send privateers on raids against the treasure fleets of Spain.

Despite the broad powers granted to Raleigh, he was forbidden to leave the queen's side. Instead of personally leading voyages to the Americas, he delegated the missions to his associates and oversaw operations from London.

Amadas–Barlowe expedition

Raleigh quickly arranged an expedition to explore his claim. It departed England on April 27, 1584. The fleet consisted of two barques; Philip Amadas was captain of the larger vessel, with Simon Fernandes as pilot, while Arthur Barlowe was in command of the other. There are indications that Thomas Harriot and John White may have participated in the voyage, but no records survive which directly confirm their involvement.

The expedition employed a standard route for transatlantic voyages, sailing south to catch trade winds, which carried them westward to the West Indies, where they collected fresh water. The two ships then sailed north until July 4, when they sighted land at what is now called Cape Fear. The fleet made landfall on July 13 at an inlet north of Hatorask Island, which was named "Port Ferdinando" after Fernandes, who discovered it.

The Native Americans in the region had likely encountered, or at least observed, Europeans from previous expeditions. The Secotan, who controlled Roanoke Island and the mainland between Albemarle Sound and the Pamlico River, soon made contact with the English and established friendly relations. The Secotan chieftain, Wingina, had recently been injured in a war with the Pamlico, so his brother Granganimeo represented the tribe in his place.

Upon their return to England in the autumn of 1584, Amadas and Barlowe spoke highly of the tribes' hospitality and the strategic location of Roanoke. They brought back two natives: Wanchese, a Secotan, and Manteo, a Croatan whose mother was the chieftain of Croatoan Island. The expedition's reports described the region as a pleasant and bountiful land, alluding to the Golden Age and the Garden of Eden, although these accounts may have been embellished by Raleigh.

Queen Elizabeth was impressed with the results of Raleigh's expedition. In 1585, during a ceremony to knight Raleigh, she proclaimed the land granted to him "Virginia" and proclaimed him "Knight Lord and Governor of Virginia". Sir Walter Raleigh proceeded to seek investors to fund a colony.

Lane colony

For the first colony in Virginia, Raleigh planned a largely military operation focused on the exploration and evaluation of natural resources. The intended number of colonists was 69, but approximately 600 men were sent in the voyage, with about half intended to remain at the colony, to be followed by a second wave later. Ralph Lane was appointed governor of the colony, and Philip Amadas would serve as admiral, although the fleet commander Sir Richard Grenville led the overall mission. Civilian attendants included Joachim Gans, metallurgist, Thomas Harriot, a scientist, and John White, an artist. Manteo and Wanchese, returning home from their visit to England, were also passengers on the voyage.

Voyage

The fleet consisted of seven ships: The galleass ''Tiger'' (Grenville's flagship, with Fernandes as pilot), the flyboat ''Roebuck'' (captained by John Clarke), ''Red Lion'' (under the command of George Raymond), ''Elizabeth'' (captained by Thomas Cavendish), ''Dorothy'' (Raleigh's personal ship, perhaps captained by Arthur Barlowe) and two small pinnaces.

On April 9, 1585, the fleet departed Plymouth, heading south through the Bay of Biscay. A severe storm off the coast of Portugal separated ''Tiger'' from the rest of the fleet and sank one of the pinnaces. Fortunately, Fernandes had a plan for such an occurrence, wherein the ships would meet up at Mosquetal, on the south coast of Puerto Rico. Proceeding alone, ''Tiger'' made good speed for the Caribbean, arriving at the rendezvous point on May 11, ahead of the other ships.

While awaiting the fleet, Grenville established a base camp, where his crew could rest and defend themselves from Spanish forces. Lane's men used the opportunity as practice for building the fortifications that would be needed at the new colony. The crew also set about replacing the lost pinnace, forging nails and sawing local lumber to construct a new ship. ''Elizabeth'' arrived on May 19, shortly after the completion of the fort and pinnace.

The remainder of the fleet never arrived at Mosquetal. At least one of the ships encountered difficulties near Jamaica and ran out of supplies, causing its captain to send twenty of his crew ashore. Eventually ''Roebuck'', ''Red Lion'', and ''Dorothy'' continued to the Outer Banks, arriving by mid-June. ''Red Lion'' left about thirty men on Croatoan Island and departed for privateering in Newfoundland. In the meantime, Grenville established contact with local Spanish authorities, in the hopes of obtaining fresh provisions. When the Spanish failed to deliver the promised supplies, Grenville suspected they would soon attack, so he and his ships abandoned the temporary fort.

Grenville captured two Spanish ships in the Mona Passage, adding them to his fleet. Lane took one of these ships to Salinas Bay, where he captured salt mounds collected by the Spanish. Lane again built fortifications to protect his men as they brought the salt aboard. Grenville's ships then sailed to La Isabela, where the Spanish set aside hostilities to trade with the well-armed English fleet. On June 7, Grenville left Hispaniola to continue to the Outer Banks.

The fleet sailed through an inlet at Wococon Island (near present-day Ocracoke Inlet) on June 26. ''Tiger'' struck a shoal, ruining most of the food supplies and nearly destroying the ship. There are indications that Grenville's fleet was supposed to spend the winter with the new colony, perhaps to immediately begin using it as a privateering base. The wreck of ''Tiger'', however, made that impossible. The remaining provisions could not support a settlement as large as had been planned. Moreover, the shallow inlets of the Outer Banks made the region unsuitable as a base for large ships. The colony's top priority would now be to locate a better harbour.

After repairs, ''Tiger'' continued with the rest of the fleet to Port Ferdinando, where they reunited with ''Roebuck'' and ''Dorothy''. The men left behind by ''Red Lion'' were presumably also located during this time. On August 5, John Arundell took command of one of the faster vessels and set sail for England, to report the expedition's safe arrival.

Establishment of the colony

The loss of provisions from the ''Tiger'' meant that the colony would support far fewer settlers than originally planned. Grenville decided that only about 100 men would stay with Lane, which would be enough to fulfill the colony's objectives until another fleet, scheduled to leave England in June 1585, could deliver a second wave of colonists and supplies. However, Grenville could not know that this expedition had been redirected to Newfoundland, to alert fishing fleets that the Spanish had begun seizing English commercial vessels in retaliation for attacks by English privateers. Until a resupply mission could be arranged, Lane's colony would be heavily dependent on the generosity of the natives.

While the ''Tiger'' was under repair, Grenville organized an expedition to explore Pamlico Sound and the Secotan villages of Aquascogoc, Pamlico, and Secotan. His party made contact with the locals, presenting Harriot and White with an opportunity to extensively study Native American society. Although much of their research did not survive the 1586 evacuation of the colony, Harriot's extensive survey of Virginia's inhabitants and natural resources was published in 1588, with engravings of White's illustrations included in the 1590 edition.

Following this initial exploration, a silver cup was reported missing. Believing the item stolen, Grenville sent Amadas to lead a detachment back to Aquascogoc to demand the return of the missing property. When the villagers did not produce the cup, the English decided that severe retribution was necessary in order to avoid the appearance of weakness. Amadas and his men burnt down the entire town and its crops, sending the natives fleeing.

Manteo arranged a meeting for Grenville and Lane with Granganimeo, to provide land for the English settlement on Roanoke Island. Both sides agreed that the island was strategically located for access to the ocean and to avoid detection from Spanish patrols. Lane began construction of a fort on the north side of the island. There are no surviving renderings of the Roanoke fort, but it was likely similar in structure to the one at Mosquetal.

Grenville set sail for England aboard the ''Tiger'' on August 25, 1585. Days later, in Bermuda, Grenville raided a large Spanish galleon, the ''Santa Maria de San Vicente'', which had become separated from the rest of its fleet. The merchant ship, which Grenville took back to England as a prize, was loaded with enough treasure to make the entire Roanoke expedition profitable, spurring excitement in Queen Elizabeth's court about Raleigh's colonisation efforts.

The ''Roebuck'' left Roanoke on September 8, 1585, leaving behind one of the pinnaces under the command of Amadas. Records indicate that 107 men remained with Lane at the colony. However, historians disagree as to whether White returned to England with Grenville, or spent the winter at Roanoke despite his absence from the list of colonists.

Exploration

Many of the colonists had joined the mission expecting to discover sources of gold and silver. When no such sources were located, these men became dispirited and decided the entire operation was a waste of their time. The English also researched where the local Native Americans obtained their copper, but ultimately never tracked the metal to its origin. The colonists spent the autumn of 1585 acquiring corn from the neighboring villages, to augment their limited supplies. The colony apparently obtained enough corn (along with venison, fish, and oysters) to sustain them through the winter. Little information survives, however, about what transpired at the colony between September 1585 and March 1586, making a full assessment of the winter impossible. The colonists most likely exhausted their English provisions and American corn by October, and the resulting monotony of their remaining food sources no doubt contributed to the men's low morale.

Amadas spent the winter exploring Chesapeake Bay, traveling as far as Cape Henry and the James River. While there his party made contact with the Chesapeake villages of Chesepioc and Skicóak. The Secotans had described Skicóak as the largest city in the region, possibly leading the English to expect something like the wealthy Inca and Aztec kingdoms encountered by the Spanish. Amadas instead found a more modest settlement, although he was impressed with the area's climate and soil quality. Harriot and Gans explored the Virginia territory, meeting Native American tribes and taking stock of natural resources. During his travels, Harriot and his assistants collected data that would eventually be used to produce White's '' La Virginea Pars'' map.

Although 16th-century science could not explain the phenomenon, Harriot noticed that each town the colonists visited quickly suffered a deadly epidemic, which may have been influenza or smallpox. Some of the Secotan suspected the disease was caused by supernatural forces unleashed by the English. When Wingina fell sick, his own people could not treat him, but he recovered after requesting prayers from the English. Impressed, Wingina asked the colonists to share this power with other stricken communities, which only hastened the spread of disease. The epidemic likely had a severe impact on the fall harvest, at a time when Lane's colony would be heavily dependent on its neighbors to supplement its limited food supply.

Hostilities and food shortages

By spring, relations between the Secotan and the colony were strained, most likely due to the colony's over-reliance on Secotan food. The death of Granganimeo, who had been a powerful advocate for the colony, apparently helped to turn Wingina against the English. Wingina changed his name to "Pemisapan" ("one who watches"), suggesting a newly cautious and vigilant policy, and established a new temporary tribal capital on Roanoke Island. The English did not initially recognize that these developments represented a threat to their interests.

In March, Lane consulted Pemisapan about a plan to explore the mainland beyond Secotan territory. Pemisapan supported the plan and advised Lane that the Chowanoke leader Menatonon was meeting with his allies to plan an attack on the English, and that three thousand warriors had gathered at Choanoac. At the same time, Pemisapan sent word to Menatonon that the English would be coming, ensuring that both sides would expect hostilities. When Lane's well-armed party arrived at Choanoac, he found representatives of the Chowanoke, Mangoak, Weapemeoc, and Moratuc. Since this gathering was not planning an attack, Lane caught them by surprise. He easily captured Menatonon, who informed him that it was Pemisapan who had requested the council in the first place.

Menatonon quickly gained Lane's trust by offering information about lucrative opportunities in lands the English had not yet discovered. He described a rich and powerful king to the northeast (presumably the leader of the Powhatan), warning that Lane should bring a considerable force if he sought to make contact. Menatonon also corroborated rumors Lane had heard about a sea just beyond the head of the Roanoke River, apparently confirming English hopes of finding access to the Pacific Ocean. The chief's son Skiko described a place to the west called "Chaunis Temoatan" rich in a valuable metal, which Lane thought could be copper or perhaps even gold.

Based on this information, Lane envisioned a detailed plan in which his forces would divide into two groups – one traveling north up the Chowan River, the other along the Atlantic coastto resettle at Chesapeake Bay. However, he decided to defer this mission until the colony received fresh supplies, which Grenville had promised would arrive by Easter. In the meantime, Lane ransomed Menatonon and had Skiko sent back to Roanoke as a hostage. He proceeded with forty men for about up the Roanoke River in search of Chaunis Temotan, but they found only deserted villages and warriors lying in ambush. Lane had expected the Moratuc to provide provisions for him along his route, but Pemisapan had sent word that the English were hostile and villagers should withdraw from the river with their food.

Lane and his party returned to the colony shortly after Easter, half-starved and empty-handed. During their absence, rumors had spread that they had been killed, and Pemisapan had been preparing to withdraw the Secotan from Roanoke Island and leave the colony to starve. There was no sign of Grenville's resupply fleet, which had not yet even left England. According to Lane, Pemisapan was so surprised that Lane returned alive from the Roanoke River mission that he reconsidered his plans. Ensenore, an elder among Pemisapan's council, argued in favor of the English. Later, an envoy for Menatonon informed Lane that the Weapemeoc leader Okisko had pledged fealty to Queen Elizabeth and Sir Walter Raleigh. This shift in the balance of power in the region further deterred Pemisapan from following through on his plans against the colony. He instead ordered his people to sow crops and build fishing weirs for the settlers.

The renewed accord between the English and the Secotan was short-lived. On April 20 Ensenore died, depriving the colony of its last advocate in Pemisapan's inner circle. Wanchese had risen to become a senior advisor, and his time among the English had convinced him that they were a threat. Pemisapan evacuated the Secotan from Roanoke, destroyed the fishing weirs, and ordered them not to sell food to the English. Left to their own devices, the English had no way to produce enough food to sustain the colony. Lane ordered his men to break up into small groups to forage and beg for food in the Outer Banks and the mainland.

Lane continued to keep Skiko as a hostage. Although Pemisapan met regularly with Skiko and believed him sympathetic to the anti-English cause, Skiko sought to honor his father's intention of maintaining relations with the colony. Skiko informed Lane that Pemisapan planned to organize a war council meeting on June 10 with various regional powers. With the copper the Secotan had gained from trading with the colony, Pemisapan was able to offer substantial inducements to other tribes to side with him in a final offensive against the English. Oksiko declined to get involved, although individual Weapemeocs were permitted to participate. The plan of attack was to ambush Lane and other key leaders as they slept at the colony, and then signal for a general attack on the rest. Based on this information, Lane sent disinformation to the Secotan indicating that an English fleet had arrived, to force Pemisapan's hand.

Forced to accelerate his schedule by the possibility of English reinforcements, Pemisapan gathered as many allies as he could for a meeting on May 31 at Dasamongueponke. That evening, Lane attacked the warriors posted at Roanoke, hoping to prevent them from alerting the mainland the following morning. On June 1, Lane, his top officers, and twenty-five men visited Dasamongueponke under the pretense of discussing a Secotan attempt to free Skiko. Once they were admitted into the council, Lane gave the signal for his men to attack. Pemisapan was shot and fled into the woods, but Lane's men caught up to him and brought back his severed head. The head was impaled outside the colony's fort.

Evacuation

In June, the colonists made contact with the fleet of Sir Francis Drake, on his way back to England from successful campaigns in Santo Domingo, Cartagena, and St. Augustine. During these raids, Drake had acquired refugees, slaves, and hardware with the intent of delivering them to Raleigh's colony. Upon learning of the colony's misfortunes, Drake agreed to leave behind four months of supplies and one of his ships, the ''Francis''. However, a hurricane hit the Outer Banks, sweeping the ''Francis'' out to sea.

After the storm, Lane persuaded his men to evacuate the colony, and Drake agreed to take them back to England. Manteo and an associate, Towaye, joined them. Three of Lane's colonists were left behind and never heard from again. Because the colony was abandoned, it is unclear what became of the slaves and refugees Drake had meant to place there. There is no record of them arriving in England with the fleet, and it is possible Drake left them on Roanoke with some of the goods he had previously set aside for Lane. Drake's fleet, along with Lane's colonists, reached England in July 1586. Upon arrival, the colonists introduced tobacco, maize, and potatoes to England.

Grenville's detachment

A single supply ship, sent by Raleigh, arrived at Roanoke just days after Drake evacuated the colony. The crew could not find any trace of the colonists and left. Two weeks later, Grenville's relief fleet finally arrived with a year's worth of supplies and reinforcements of 400 men. Grenville conducted an extensive search and interrogated three natives, one of which finally related an account of the evacuation. The fleet returned to England, leaving behind a small detachment of fifteen men both to maintain an English presence and to protect Raleigh's claim to Roanoke Island.

According to the Croatan, this contingent was attacked by an alliance of mainland tribes shortly after Grenville's fleet left. Five of the English were away gathering oysters when two of the attackers, appearing unarmed, approached the encampment and asked to meet with two Englishmen peacefully. One of the Native Americans concealed a wooden sword, which he used to kill an Englishman. Another 28 attackers revealed themselves, but the other Englishman escaped to warn his unit. The natives set fire to the house where the English kept their food stores, thus forcing the men to take up whatever arms were handy. A second Englishman was killed; the remaining nine retreated to the shore, and fled the island on their boat. They found their four compatriots returning from the creek, picked them up, and continued onto a small island near the entrance to the Hatteras harbor. The thirteen survivors were never seen again.

Lost colony

Despite the desertion of the Lane colony, Raleigh was persuaded to make another attempt by Hakluyt, Harriot, and White. However, Roanoke Island would no longer be safe for English settlers, following the hostilities between Lane's men and the Secotan, and the death of Wingina. Hakluyt recommended Chesapeake Bay as the site for a new colony, in part because he believed the Pacific coast lay just beyond the explored areas of the Virginia territory. On January 7, 1587, Raleigh approved a corporate charter to found "the Cittie of Raleigh" with White as governor and twelve assistants. Approximately 115 people agreed to join the colony, including White's pregnant daughter Eleanor and her husband Ananias Dare. The colonists were largely middle-class Londoners, perhaps seeking to become landed gentry. Manteo and Towaye, who had left the Lane colony with Drake's fleet, were also brought along. This time, the party included women and children, but no organized military force.

The expedition consisted of three ships: The flagship ''Lion'', captained by White with Fernandes as master and pilot, along with a flyboat (under the command of Edward Spicer) and a full-rigged pinnace (commanded by Edward Stafford). The fleet departed on May 8.

On July 22, the flagship and pinnace anchored at Croatoan Island. White planned to take forty men aboard the pinnace to Roanoke, where he would consult with the fifteen men stationed there by Grenville, before continuing on to Chesapeake Bay. Once he boarded the pinnace however, a "gentleman" on the flagship representing Fernandes ordered the sailors to leave the colonists on Roanoke.

The following morning, White's party located the site of Lane's colony. The fort had been dismantled, while the houses stood vacant and overgrown with melons. There was no sign that Grenville's men had ever been there except for human bones that White believed were the remains of one of them, killed by Native Americans.

Following the arrival of the flyboat on July 25, all of the colonists disembarked. Shortly thereafter, colonist George Howe was killed by a native while searching alone for crabs in Albemarle Sound.

White dispatched Stafford to re-establish relations with the Croatan, with the help of Manteo. The Croatan described how a coalition of mainland tribes, led by Wanchese, had attacked Grenville's detachment. The colonists attempted to negotiate a truce through the Croatan, but received no response. On August 9, White led a pre-emptive strike on Dasamongueponke, but the enemy (fearing reprisal for the death of Howe) had withdrawn from the village, and the English accidentally attacked Croatan looters. Manteo again smoothed relations between the colonists and the Croatan. For his service to the colony, Manteo was baptized and named "Lord of Roanoke and Dasamongueponke".

On August 18, 1587, Eleanor Dare gave birth to a daughter, christened "Virginia" in honor of being "the first Christian born in Virginia". Records indicate Margery Harvye gave birth shortly thereafter, although nothing else is known about her child.

By the time the fleet was preparing to return to England, the colonists had decided to relocate up Albemarle Sound. The colonists persuaded Governor White to return to England to explain the colony's desperate situation and ask for help. White reluctantly agreed, and departed with the fleet on August 27, 1587.

1588 relief mission

After a difficult journey, White returned to England on November 5, 1587. By this time reports of the Spanish Armada mobilizing for an attack had reached London, and Queen Elizabeth had prohibited any able ship from leaving England so that they might participate in the coming battle.

During the winter, Grenville was granted a waiver to lead a fleet into the Caribbean to attack the Spanish, and White was permitted to accompany him in a resupply ship. The fleet was set to launch in March 1588, but unfavorable winds kept them in port until Grenville received new orders to stay and defend England. Two of the smaller ships in Grenville's fleet, the ''Brave'' and the ''Roe'', were deemed unsuitable for combat, and White was permitted to take them to Roanoke. The ships departed on April 22, but the captains of the ships attempted to capture several Spanish ships on the outward-bound voyage (in order to improve their profits). On May 6 they were attacked by French mariners (or pirates) near Morocco. Nearly two dozen of the crew were killed, and the supplies bound for Roanoke were looted, leaving the ships to return to England.

Following the defeat of the Spanish Armada in August, England maintained the ban on shipping in order to focus efforts on organizing a Counter Armada to attack Spain in 1589. White would not gain permission to make another resupply attempt until 1590.

Spanish reconnaissance

The Spanish Empire had been gathering intelligence on the Roanoke colonies since Grenville's capture of ''Santa Maria de San Vicente'' in 1585. They feared that the English had established a haven for piracy in North America, but were unable to locate such a base. They had no cause to assume Lane's colony had been abandoned, or that White's would be placed in the same location. Indeed, the Spanish greatly overestimated the success of the English in Virginia; rumors suggested the English had discovered a mountain made of diamonds and a route to the Pacific Ocean.

Following a failed reconnaissance mission in 1587, Philip II of Spain ordered Vicente González to search Chesapeake Bay in 1588. González failed to find anything in Chesapeake, but on the way back he chanced to discover Port Ferdinando along the Outer Banks. The port appeared abandoned. González left without conducting a thorough investigation. Although the Spanish believed González had located the secret English base, the defeat of the Spanish Armada prevented Phillip from immediately ordering an attack upon it. In 1590, a plan was reportedly made to destroy the Roanoke colony and set up a Spanish colony in Chesapeake Bay, but this was merely disinformation designed to misdirect English intelligence.

1590 relief mission

Eventually, Raleigh arranged passage for White on a privateering expedition organized by John Watts. The fleet of six ships would spend the summer of 1590 raiding Spanish outposts in the Caribbean, but the flagship ''Hopewell'' and the ''Moonlight'' would split off to take White to his colony. At the same time, however, Raleigh was in the process of turning the venture over to new investors.

''Hopewell'' and ''Moonlight'' anchored at Croatoan Island on August 12, but there is no indication that White used the time to contact the Croatan for information. On the evening of August 15, while anchored at the north end of Croatoan Island, the crews sighted plumes of smoke on Roanoke Island; the following morning, they investigated another column of smoke on the southern end of Croatoan, but found nothing. White's landing party spent the next two days attempting to cross Pamlico Sound with considerable difficulty and loss of life. On August 17 they sighted a fire on the north end of Roanoke and rowed towards it, but they reached the island after nightfall and decided not to risk coming ashore. The men spent the night in their anchored boats, singing English songs in hopes that the colonists would hear.

White and the others made landfall on the morning of August 18 (his granddaughter's third birthday). The party found fresh tracks in the sand, but were not contacted by anyone. They also discovered the letters "CRO" carved into a tree. Upon reaching the site of the colony, White noted the area had been fortified with a palisade. Near the entrance of the fencing, the word "CROATOAN" was carved in one of the posts. White was certain these two inscriptions meant that the colonists had peacefully relocated to Croatoan Island, since they had agreed in 1587 that the colonists would leave a "secret token" indicating their destination, or a cross pattée as a duress code.

Within the palisade, the search party found that houses had been dismantled, and anything that could be carried had been removed. Several large trunks (including three belonging to White, containing the belongings he left behind in 1587) had been dug up and looted. None of the colony's boats could be found along the shore. The party returned to ''Hopewell'' that evening, and plans were made to return to Croatoan the following day. However, ''Hopewell''s anchor cable snapped, leaving the ship with only one working cable and anchor. The search mission could not continue given the considerable risk of shipwreck. ''Moonlight'' set off for England, but the crew of ''Hopewell'' offered a compromise with White, in which they would spend winter in the Caribbean and return to the Outer Banks in the spring of 1591. This plan fell through, though, when ''Hopewell'' was blown off course, forcing them to stop for supplies in the Azores. When the winds prevented landfall there, the ship was again forced to change course for England, arriving on October 24, 1590.

Investigations into Roanoke

1595–1602: Walter Raleigh

Although White failed to locate his colonists in 1590, his report suggested they had simply relocated and might yet be found alive. However, it served Raleigh's purposes to keep the matter in doubt; so long as the settlers could not be proven dead, he could legally maintain his claim on Virginia. Nevertheless, a 1594 petition was made to declare Ananias Dare legally dead so that his son, John Dare, could inherit his estate. The petition was granted in 1597.

During Raleigh's first transatlantic voyage in 1595, he claimed to be in search of his lost colonists, although he later admitted this was misinformation to cover his search for El Dorado. On the return voyage, he sailed past the Outer Banks, and later claimed that weather had prevented him from landing.

Raleigh later sought to enforce his monopoly on Virginia – based on the potential survival of the Roanoke colonists – when the price of sassafras skyrocketed. He funded a 1602 mission to the Outer Banks, with the stated goal of resuming the search. Led by Samuel Mace, this expedition differed from previous voyages in that Raleigh bought his own ship and guaranteed the sailors' wages so that they would not be distracted by privateering. However, the ship's itinerary and manifest indicate that Raleigh's top priority was harvesting sassafras far south of Croatoan Island. By the time Mace approached Hatteras, bad weather prevented them from lingering in the area. In 1603, Raleigh was implicated in the Main Plot and arrested for treason against King James, effectively ending his Virginia charter.

1603: Bartholomew Gilbert

There was one final expedition in 1603 led by Bartholomew Gilbert with the intention of finding the Roanoke colonists. Their intended destination was Chesapeake Bay, but bad weather forced them to land in an unspecified location near there. The landing team, including Gilbert himself, was killed by a group of Native Americans for unknown reasons on July 29. The remaining crew were forced to return to England empty-handed.

1607–1609: John Smith

Following the establishment of the Jamestown settlement in 1607, John Smith was captured by the Powhatan and met with both their leader Wahunsenacawh (often referred to as "Chief Powhatan") and his brother Opechancanough. They described to him a place called "Ocanahonan", where men wore European-style clothing; and "Anone", which featured walled houses. Later, after Smith returned to the colony, he made arrangements with Wowinchopunk, the king of the Paspahegh, to investigate "Panawicke", another place reportedly inhabited by men in European dress. The colony produced a crude map of the region with labels for these villages. The map also featured a place called "Pakrakanick" with a note indicating, "Here remaineth four men clothed that came from Roonocok to Ocanahawan."

In the summer of 1608, Smith sent a letter about this information, along with the map, back to England. The original map is now lost, but a copy was obtained by Pedro de Zúñiga, the Spanish ambassador to England, who passed it on to Philip III of Spain. The copy, now commonly referred to as the "Zúñiga Map", was rediscovered in 1890.

Smith planned to explore Pakrakanick, but a dispute with the Paspahegh ended the mission before it could begin. He also dispatched two search parties, possibly to look for the other villages reported to him, with instructions to find "the lost company of Sir Walter Rawley". Neither group could find any sign of the Roanoke colonists living in the area.

By May 1609, word had reached England's Royal Council for Virginia that the 1587 colonists had been massacred by Wahunsenacawh. The source of this allegation is unknown. Machumps, Wahunsenacawh's brother-in-law, is known to have provided information about Virginia, and he had recently arrived in England. It has been speculated that the same voyage could have also delivered a letter from Smith, although no evidence for this exists.

Based on this intelligence, as well as Smith's earlier report, the Council drafted orders for the Jamestown colony to relocate. These orders recommended "Ohonahorn" (or "Oconahoen"), near the mouth of the Chowan River