Although Ocracoke did not play a major role in the first attempts by the English to colonize America, Ocracoke is part of the story from the first voyage led by Philip Amadas and Arthur Barlowe in 1584 until John White returns to search for his “lost” colony in 1590.
The English made five voyages of discovery and colonization from 1584 to 1590. Without going into great detail (many books have already been written about this period of American history), I will present highlights of the voyages with snippets of information regarding Ocracoke Island, mostly taken from accounts recorded by Richard Hakluyt, an Elizabethan historian, as transcribed by Andrew Thomas Powell.*
On April 27, 1584 two “barkes well favoured with men and victuals left England for the New World. Commissioned by Sir Walter Raleigh pursuant to a grant from Queen Elizabeth I, and under the command of Philip Amadas and Arthur Barlowe, this first expedition explored that portion of “Virginia” (originally the entire east coast of North America) that we know today as the Outer Banks of North Carolina.
Sir Walter Raleigh:
On July 4 Amadas and Barlowe arrived “upon the coast” (the precise location is difficult to determine from Hakluyt’s account), then sailed north some distance and explored an island (perhaps the “isle of Wokokon,” [Ocracoke] or more likely a part of the northern Outer Banks). Hakluyt describes the island as containing “many goodly woods, and full of deer, conies [rabbits], hares, and fowl…in incredible abundance.”
After several days the English encountered various natives with whom they traded and visited, both aboard their ships, and in native villages on the mainland and on Roanoke Island. Hakluyt goes on to describe many customs and manners of the native people.
While exploring this area the English learned of “a ship cast away” “five and twenty years past.” These white castaways, almost certainly Spaniards, remained several weeks, according to the natives, on “an out island unhabited, called Wococan.” With help from the residents from Sequotan, a village on the mainland, they departed in a makeshift vessel of two boats fastened together, and “were cast away, for the boats were found upon the coast, cast aland in another island adjoining [very likely Portsmouth Island].”
Sequotan (Secotan), a Drawing by John White, 1585:
Hakluyt describes Ocracoke as “unhabited,” but two early maps, White-DeBry from 1590 and Mercator-Hondius from 1606, clearly show one settlement on the island. Although no archaeological evidence of a permanent village on Ocracoke has yet been discovered, a number of Native American arrowheads and pipe bowls have been found on the island.
About the middle of September  Amadas and Barlowe’s ships returned to England.
In the spring of 1585 Sir Richard Grenville, commanding seven ships and several hundred men, set sail from Plymouth, England on the second of Sir Walter Raleigh’s expeditions. The goal was to establish a military colony on Roanoke Island under the leadership of Ralph Lane. In June they anchored at the Spanish port of Isabella, on the north side of Hispaniola (the island of Haiti and the Dominican Republic).
There, according to Hakluyt, they traded for many “commodities of the Island” including horses. Andrew Powell, in his book, Grenville & the Lost Colony of Roanoke, observes that “this is clear evidence that Grenville’s vessel did have Spanish horses on board when it arrived at the Outer Banks.” He goes on to speculate, “Might the progeny of these bartered-for horses of Hispaniola be the Ocracoke Banker horses of today?”
Hakluyt says that on “the 26th [of June] we came to anchor at Wocokon. The 29th we weighed anchor to bring the Tyger [the Grenville fleet’s flagship] into the harbour [the calmer waters of Pamlico Sound…not Silver Lake Harbor], where through the unskillfulness of the Master whose name was Fernando, the Admiral [the flagship Tyger] stroke on ground, and sunk.” The wreck of the Tyger at Ocracoke Inlet in 1585 is the first recorded shipwreck along the Outer Banks.
John White’s Map of “Virginia,” 1585:
In a letter dated Aug. 12, 1585 from Roanoke Island, Ralph Lane writes to Sec. Walsingham in England: “There are only three entries and ports; these they have named, Trinity, Scarborough, and Ococan, where their fleet struck aground, and Tyger was nearly lost.” Ocracoke (Ococan) Inlet is the only inlet that has remained open continuously since 1585. We cannot be certain where the other two inlets were located.
For nearly a month Grenville’s fleet remained at Ocracoke while various members of the party explored native villages on the mainland. In the process they burned a village and destroyed crops in retaliation for a silver cup they believed stolen by the “savages.” By the 27th of June the Englishmen had anchored at Hatoraske.
On August 17, 1585 Ralph Lane and a band of 107 men arrived at Roanoke Island where they established their military colony. The fleet with the remaining sailors, under command of Grenville, returned to England where they made port by mid October.
On Roanoke Island a number of unfortunate conflicts with the natives ensued. Relations deteriorated rapidly after the English attacked a village and killed their chief, Wingina.
Ralph Lane, in his account of the military colony’s occupation, mentions that the natives “live upon shellfish…going to Ottorasko [Hatteras], Crotoan [an island that is now the northern part of Ocracoke and the southern part of Hatteras], and other places [presumably Wococon] fishing and hunting, while their grounds be in sowing, and their corn growing….”
As it happened, Sir Francis Drake arrived at Roanoke in June, 1586. A severe storm convinced Lane to accept Drake’s offer of passage to England, and he departed with the military men on June 18, 1856. As promised, Raleigh had sent two expeditions under the command of Grenville to re-supply the colony, but they arrived a few days after Drake left with the colonists. After searching Roanoke and surrounding areas without finding any of the colonists Grenville left fifteen men on the island with “all manner of provision for two years” and returned to England.
The second English colony, intended as a permanent settlement, and consisting of 117 English men, women and children, and two “savages” who were returning home, departed Portsmouth, England April 26, 1587 in three ships bound for Virginia. They disembarked on Hatteras Island, and traveled to Roanoke in small boats.
Arriving at Roanoke in July they found none of the fifteen men who had been left there the previous year. However they did find the skeleton of one of the men who had been killed by the natives. The English immediately set about repairing the existing houses and establishing their colony.
In spite of a series of mishaps, including skirmishes with the natives and violent storms, the colony showed signs of stability when Manteo, one of the natives who had accompanied Grenville to England and back, helped foster friendly relations between his people on Croatoan and the English. On August 13 Manteo was baptized.
On August 18 Virginia Dare, granddaughter of John White, governor of the colony, was born. She was the first English child born in the New World.
The Baptism of Virginia Dare:
Nine days later John White departed for England, intending to return the next year. On November 5 he landed at Martesew near Cornwall.
White’s efforts to return to Virginia in 1588 were thwarted when his ships were pressed into service by the crown because of war with Spain.
It was not until March 20, 1590 that three ships, the Hopewell, the John Evangelist and the Little John left Plymouth, England with two small shallops (small open boats propelled by oars and sails). By August they stopped at the “Low sandy Islands West of Wokokon” (Portsmouth Island and Core Banks) to collect fresh water and catch a “great store of fish in the shallow water.”
On the 17th of August White’s party approached Roanoke. While trying to navigate a treacherous inlet one small boat capsized, drowning seven sailors. When White and his company finally made their way to the settlement they discovered no colonists. However the word CROATOAN was carved into a tree. This was the agreed upon “secret token” explaining where the colonists could be found if they needed to remove themselves from Roanoke. It was not accompanied by a cross, the agreed upon sign of distress.
John White Discovers CROATOAN carved into a Tree:
The expedition attempted to reach Croatoan, but were forced away by foul weather. At one time the wind “blew so forcibly, that we were able to bear no sail…wherewith we ran upon the wind perforce, the due course for England.” They arrived at Plymouth, England October 24.
No further attempts were made to contact the colony of 1587.
There is ample reason to believe that the English colonists were integrated with the friendly Croatan Indians on the island of Croatoan, and that their descendants inhabit Hatteras Island, and perhaps Ocracoke Island, to this day. There is also reason to think that a portion of the “lost” colony may have intermarried with mainland North Carolina Indians.
* Grenville & The Lost Colony of Roanoke, by Andrew Thomas Powell, 2011
Other books of interest regarding the early English voyages of exploration and colonization include The Outer Banks of North Carolina, 1584-1958, by David Stick, 1958, and Croatoan: Birthplace of America, by Scott Dawson, 2009.