Between the Warraskoyaks and the Nansemonds lay an area of creeks and marshes to the east of the Pagan River. To the west were Quiyoughcohannock, who, like the Warraskoyak, were a more peaceful and accomodating tribe than the Nansemonds. They were ruled by Tatahcoope, one of Powhatan's sons. In the spring of 1609, this tribe provided guides to conduct an English expedition in search of any survivors of the 1587 Roanoke colony. This tribe inhabited territory on the opposite shore to Jamestown and contact with the Jamestown settlers took the form of the regular provision of food.
"Choapock: weeroance of the Quiocquahanocks did always at our greatest need supply us with victuals of all sorts, which he did notwithstanding the continual wars which we had in the rest of the country, and upon his deathbed charged his people that they should forever keep good quiet with the English. Pippisco now weeroance doth not forget his predecessor's testament". [See Jamestown Narratives, page 148 by Edward Wright Haile. From John Smith's "A True Relation"]
Indeed, the tribes south of the James River, with the exception of the Nansemonds, were relatively weak and were therefore more responsive to a show of force and consequently were more open to conciliation with the settlers. It would seem that they had few warriors even to protect themselves. In "Notes on the State of Virginia", Thomas Jefferson reviewed various aspects of the state of Virginia and one area was an overview of the native tribes. In a table, he provides information on the tribe, their home town and numbering their fighting strength in 1607 and 1669. The "Quicochanocs" had twenty five warriors in 1607 and had been reduced to "3 Phoics" in 1669, while the figures for the "Warrasqueaks" were left blank. The Warraskoyaks may have been linked with two subordinate tribes, the Alokete and the Mathomauk, both living in near proximity. The Nansemonds, however possessed two hundred warriors in 1607, and still had forty five in 1669. No wonder the Quiocquahanocks and the Warraskoyaks were more amenable than the Nansemonds.
The original settlers arrived in April 1607 and , for defence reasons, chose a marshy peninsular - a presqu'ile - , on which to site their settlement which they called Jamestown. From here expeditions went out to explore the region under the command of Capt. John Newport or Capt. John Smith.
In the summer of 1607, after having returned from reconnoitring the shores up-river, Smith continued his explorations, following the river down to Kiccoughtan (Kecoughtan) and across to Warraskoyack (Isle of Wight), making journeys along the shore line, exploring the creeks, etc., in that section. In the fall he began mapping out the country along the banks of the Chickahominy, exploring the river as far as possible for him to use a canoe.
And so, the situation that faced the English colonists in the first few years was desparate. They could not grow enough food to sustain themselves and they could not subjugate the local Indian confederacy under the chief Powhatan. They understandably feared that he could wipe them out with a concerted attack, while they remained dependent on supplies that his people could supply from their agricultural surpluses. Captain John Smith continually met groups of the neighbouring tribes on his journies of exploration into the hinterland and surrounding waterways. It was during these early forages for food supplies that the colonists came into contact with, amongst others, the Warraskoyak tribe.
In September 1607, on finding only eighteen days worth of supplies left, Smith set off down to Kecoughtan to trade for corn and "try the river for fish". Once there, he was able to obtain fish, oysters, bread, venison and sixteen bushels of corn. On his return journey, Smith came across two Warraskoyak canoes and managed to trade for fourteen more bushels of corn.
As well as trying to find gold and a route through to the Far East, the colonists were also instructed to search for the lost colonists of the 1587 Roanoke settlement. In February 1608, two colonists set off with guides from the Paspahegh tribe and their werowance, Wowinchopunk to find any survivors. However they merely went down to the Warraskoyak, who allowed them to stay for several days, before returning and "deluding us for rewards". Again, on 29 December 1608, Capt. John Smith and thirty eight men set out from Jamestown for Powhatan's capital at Werowocomoco in order to trade for corn and provisions for the stricken colony. That night, they bivouaced in the territory of the Warraskoyak and Smith met their leader, Tackonekintaco. Smith requested guides to accompany Michael Sicklemore on his journey south into the Chowanoc country. Sicklemore was described by Smith as "a very honest, valiant, and painful (Painstaking, conscientious.) soldier" and he was provided with two Warraskoyak men and "directions how to search for the lost Company of Sir Walter Rawley, and silk grass".
"This company being victualled but for 3 or 4 days lodged the first night at Weraskoyack, where the President took sufficient provision; This kind savage did his best to divert him from seeing Powhatan, but perceiving he could not prevail, he advised in this manner Captain Smith, "you shall find Powhatan to use you kindly, but trust him not, and be sure he have no opportunity to seize on your arms, for he hath sent for you only to cut your throats;" the Captain thanked him for his good counsel, yet the better to try his love, desired guides to Chowanoke, for he would send a present to that king to bind him his friend. To perform this journey, was sent Michael Sicklemore, a very honest, valiant, and painful soldier, with him two guides, and directions how to search for the lost company of Sir Walter Raleigh, and silk grass: then we departed thence, the President assuring the king his perpetual love, and left with him Samuell Collier his page to learn the language..." (John Smith: The Proceedings of the English Colony in Virginia, 1612)
Sicklemore was gone for three months but found nothing. It is clear that the Warraskoyak chief was keen to establish good relations with John Smith and the English colonists and did not present a hostile face. This apparent friendliness induced Smith to leave his page, Samuell Collier, to learn the language, Algonquin, one of the three major native American language groups. Indeed, being so close to James town, the Warraskoyak were one of several local tribes who, as Captain Newport observed, all came paddling up with food to barter for "beads and cloth", pins, bells etc. from a ship off Jamestown. It would also seem that Warraskoyak was a convenient stopping-off place on any outward expeditions from Jamestown.
Again the amenable nature of this tribe was highlighted in 1622 by the fact that Browne, a servant of Captaine Hamor, returned from living with the Warraskoyaks, where he had been placed to learn the language.("A declaration of the State of the Colony and Affaires in Virginia. With a relation of the barbarous massacre..." 1622. Edward Waterhouse.)
The name 'Warraskoyak' continued to be used as the collective name for the plantations in this area until 1634 when the first 8 official counties of Virginia were established and their boundaries fixed. The term 'Warraskoyak' finally faded away as the new county name, Isle of Wight County, took its place, symbolising the replacement of a native American population with an English presence.