January 6, 1585 - Sir Walter Raleigh is knighted by Queen Elizabeth who appoints him Lord of the new territories that he will discover in North America.
February, 1585 - Queen Elizabeth grants a charter to Adrian Gilbert, the young brother of Sir Humphrey Gilbert, allowing him to sail north, northwest and northeast with so many ships as he could, with the aim of colonizing all the lands that he would discover.e will discover in order to set up a trade monopoly.
Sir Humphrey Gilbert and Martin Frobisher's failures had not appeased the enthusiasm of those who sought to find the Northwest Passage. Adrian Gilbert, the philosopher John Dee and Secretary of State Sir Francis Walsingham had joined for further research. They will organize, to this end, several expeditions but none will achieve results.
April 9, 1585 - the 5-ship expedition commanded by Sir Walter Raleigh’s cousin, Sir Richard Grenville, newly appointed General of Virginia, leaves Plymouth with a group of 600 would-be settlers and sets sail to Roanoke, North Carolina.
With the Tiger, a 140 ton-vessel commanded by Sir Richard Grenville himself, who was also the biggest ship, the others being the Roebuck (140 tons, John Clark captain), the Red Lion (100 tons, owned and captained by George Raymond, a merchant-adventurer from Chichester), the Elizabeth and the Dorothy. Among the present officers were both veterans Philip Amadas and Simon Fernandes, but also Thomas Cavendish who will later become the third sailor to perform a full world tour, John Arundell, Grenville's half brother and John Stukeley, his brother-in-law.
There were also cousins and friends of Raleigh including Richard Gilbert, a Courtenay, a Prideaux, Ralph Lane and Anthony Rose. There were finally an illustrator, John White, two scientists, Thomas Harriot and Robert Hues, and among the most humble, an Irishman named Darby Glande. Both Indians Winchese and Manteo were part of the trip.
The chosen route was to pass Canary Islands and the Spanish West Indies.
May 12, 1585 - After suffering a storm in the Bay of Portugal, the Grenville's fleet casts anchor in Mosquito Bay, Puerto Rico. The Roebuck and the Red Lion have followed other routes. Grenville orders the building of a fort and the fitting out of a small smithy. He also asks his men to build a new rowboat intended to replace the one lost in the gale.
Tired of waiting in vain the missing ships, the Raleigh expedition left late May Puerto Rico, not without having previously burnt the fort and the neighboring woods, nor forgetting, by the way, to loot two Spanish frigates, proving that England and Spain were virtually at war. The open conflict was going to burst only three years later but, at that time, the British felt involved in a sort of "cold war" due to the fact that already based in Florida, Spain saw unfavorably the English colonial attempts in the North American continent. Their ambitions went against the Spaniards' interests who feared that they would directly affect their trade with the New World. And it was obvious that such possibility was essential for Raleigh and Grenville who hoped seriously to finance their colonial program by piecemeal privateering against the Spanish galleons.
June 1, 1585 - Having reached the island of Hispaniola, the English fleet casts anchor in the port of La Isabela where Grenville invites the residents to go aboard the Tiger.
June 3, 1585 - the Spanish governor agrees Grenville's invitation to have dinner at his table and goes aboard the Tiger.
This one felt flattered of this attention and allowed back Grenville and his men to get all the supplies required for their settlement: horses, mares, cows, bulls, goats, pigs, sheep, sugar, etc....
June 8, 1585 - Grenville and his men leave La Isabela to the Bahamas from where they have to set sail to the North American coast.
June 16, 1585 - The Red Lion, commanded by captain George Raymond, arrives at Cape Hatteras. About thirty men are landed on Croatoan Island looking forward to the other boats of the Raleigh expedition while Raymond decides for his part to leave to Newfoundland for a privateering campaign.
Grenville's fleet had been dispersed further to a storm off the Bay of Portugal and the Red Lion had since followed an other route.
June 26, 1585 - the expedition reaches Wococon Island (today Ocracoke) South of Cape Hatteras.
June 29, 1585 - Despite his pilot's skills, Simon Fernandes fails to steer properly the Tiger when crossing the Wococon inlet and causes an important waterleak damaging the major part of the provisions.
This incident was even more disastrous than while provisions had initially to allow the colony to survive for a year, what was left insured its livelihood for barely a month. Fernandes caused accordingly a lot of resentment among the colonists.
July 3, 1585 - Grenville sends Winchese and a small company to inform King Wingina of their arrival.
Unlike Manteo who was rather well accustomed to the English manners, Winchese had never really agreed to be hauled despite him to England and just arrived at Dasamonquepeuc, he hastened to chase away his guides, informing his tribe that the newcomers were not as trustworthy as they believed.
July 6, 1585 - Grenvile's half-brother John Arundell is sent with Manteo to Croatoan Island where they find the men landed shortly before from the Red Lion.
July 11, 1585 - Grenville leaves for exploration in mainland accompanied with about sixty men and the Indian Manteo.
July 12, 1585 - The English visit the village of Pomeiooc where lives Pemiacum, a rival of Wingina. John White makes on this occasion spectacular watercolor sketches of the town with longhouses and palisade around it.
July 13, 1585 - the settlers go to Aquascogok.
July 15, 1585 - Grenville and his men are welcomed at Secotan.
Unlike the previous year, the Indians remained divided on the reception to be reserved to the foreigners. Their return had been preceded by strange phenomena as a total solar eclipse and the appearance of a comet but the most worrying came from the insidious arrival of a disease that recently began to decimate the Native population.
July 16, 1585 - Sir Richard Grenville sends Admiral Phillip Amadas to Aquascogok to get back a silver cup stolen during his visit. The Indians not being decided to do so, the order is given to chase away all the inhabitants and to burn the village and the corn crops.
Grenville triggered the Secotan's anger by not hesitating to sack and make burn down the whole village of Aquascogok for the simple theft of a silver cup. What ordered Grenville reflected that the English culture was unable to consider the Natives otherwise than as savages and treat them accordingly.
July 21, 1585 - Leaving Wococon, Grenville sets sail following the outer banks northbound up to Roanoke. He meets Granganimeo, King Wingina's brother in Dasamonquepeuc and asks him to allow his group to settle in the north of the island.
July 27, 1585 - Grenville anchors at Hatoraske, not far from the strip of coastal dunes, at a short distance from Roanoke.
There was then real tensions between officers an gentlemen and mainly between Sir Richard Grenville and Ralph Lane, a veteran allied to Sir Francis Walsingham who was less concerned with the founding of a colony than to engage fight against the Spaniards whose strengths he judged rather weak. The colony finally settled in the northern end of Roanoke Island and Ralph Lane was appointed the first governor. He sent a letter to Sir Phillip Sidney, the son-in-law of Walsingham who closely followed the New World's exploration, informing him about the success of the expedition. In another letter to geographer and historian Richard Hakluyt, the new governor of Virginia pointed out that he was really impressed by the immensity of this unknown continent. He added that if the colony had horses and cows in reasonable quantities and was inhabited by Englishmen, no realm of Christendom would be comparable to it.
The Natives he described naively as courteous and eager to wear clothes, seemed chiefly interested in red copper. Their leader Wingina received the English with hospitality and cooperated with them at the beginning of their settlement.
August 25, 1585 - Grenville returns to England for provisions. He leaves on Roanoke 107 men under new governor Ralph Lane.
On the way back, Grenville seized a Spanish galleon whose booty was used to pay off generously the costs incurred during the expedition. Upon his arrival in England, he reported to Walsingham who confirmed him all the interest of the Queen to his project and insisted on the "national" character of the Virginian venture. According to Ralph Lane, Grenville was especially, as General of Virginia, noted for his brutality and tyrannical conduct. He relied on the foresight of Sir Walter Raleigh to move him aside from the project of colonization, for his pride and immoderate ambition had more endangered the settlement than contributed to its safety.
September 3, 1585 - Ralph Lane writes a letter to Richard Hakluyt describing the new colony as "the goodliest and most pleasing territorie of the world".
Lane built a small fort he called Fort Raleigh the remains of which were still visible in 1896. It was located near the shore, on the East Coast of Roanoke between the northern point and a rather wide cove used as mooring for small boats. The fort looked like the one previously built in Puerto Rico forming a square strengthened by fitted out bastions in the middle of each side.
The houses of the first settlers were nearby. They were, according to their occupants, simple but decent. Roofs were thatched and chimneys, as foundations, were to be brick-built, according to Darby Glande’s report. Vestiges discovered nearby in 1860 and recent excavations have indeed unearthed the remains of bricks probably going back up to the Elizabethan time. Thomas Harriot found that there was no stone on the island but the presence of clay could serve to make bricks and it was possible to obtain lime from oyster shells deposits, as were particularly in England on the islands of Tenet and Shepy.
As the searches were not however able to highlight the significant use of the brick, it is reasonable to assume that the main construction material was wood. Richard Hakluyt, in his "Discourse of Western Planting" wrote that the will of Sir Walter Raleigh, dictated in 1584, one year before the expedition started, was to have it mostly composed with expert hands in the art of fortification, people knowing to manufacture blades and shovels, shipwrights, carpenters, brickworkers, tile makers, whitewashers, masons, roofers, thatchers, etc.... It is assumed that the buildings erected at Roanoke by the craftsmen were widely inspired by traditional English cottages.
Relationship with the American Natives was initially friendly although the English settlement did not please everyone at the tribe's Council. The Indians made sowings and laid fishtraps while the colonists used their diplomatic skills to convince their leader Wingina to farm at the same time his lands on Roanoke and those around Dasamonquepeuc, so that they could supply them if their settlement grew.
The coast was explored to the South until Secotan (c. 80 miles) and to the North until Chesapeake (c. 130 miles). Thomas Harriot gathered information on plants, animals and stones. John White made inimitable watercolour paintings of the Secotan life in Roanoke and the coast. The settlers also learned to smoke tobacco by using Indian pipes.
It is unclear to what extent the first settlers conformed to the criteria laid down by Richard Hakluyt but records tell that there were experts in fortification, brickmakers, carpenters and roofers. We also know the name of the colonists. Thomas Harriot teaches us that some of them were highborn citizens who became fast nostalgic of their cosy bed and delicate food. Others, according to Lane's testimony, were excellent soldiers. There were also people of humble condition of whom Darby Glande had to be the representative and who, although Irish, had certainly taken part in the expedition without having really chosen.
This expedition looked more like a military campaign than a genuine settlement.