The marsh along Bland creek just south of Werowocomoco.

Werowocomoco at the Time of English Settlement, 1607-1609

The paucity of historical records concerning the earliest years of English contact with the Virginia Indians leave historians and archaeologists with a limited but colorful account of cultural interaction at Werowocomoco. John Smith's A True Relation describes his December 1607 capture near the headwaters of the Chickahominy River by warriors loyal to Powhatan's brother, Opechancanough. Smith and his party were taken to "Waranacomoco upon the River of Pamauncke [York], where the great king [Powhatan] is resident." During his stay at Werowocomoco, Smith used the Spaniards as an excuse for the English presence in Powhatan territory and divulged the need to "revenge" the death by grisly torture of one of their party by what he supposed to be members of the neighboring Monacans. Powhatan informed Smith of the lands and peoples under his control and of his neighbors and enemies (including the Monacan). Smith describes the "River of Pamauncke" as "not past twelve miles from that we dwell on [the James], his course northwest and westerly as the other” with “Weraocomoco" being "upon salt water in breadth two miles." This meeting is later elaborated upon in The General History: The Third Book to include Smith's rescue by Pocahontas.

Late in February of 1608, Smith returned to Werowocomoco with Captain Newport and a group of 30-40 armed men for an official visit to discuss relations between the two groups. Smith describes the bay upon which Werowocomoco was sited as having "3 creeks, and a mile and a half from the channel all ooze," the three creeks mentioned being in all likelihood present-day Caffee, Leigh, and Purtan Creeks, and the "ooze" needing no explanation to anyone who has been up any of them. Smith found himself "mistaken in the creek, for they all there were within less than a mile," a description which closely matches the layout of creeks feeding into Purtan Bay.

Smith's later embellishment of his meeting with Powhatan in The General History: The Third Book includes details of the trade of an English boy (Thomas Salvage) for a Native American (Namontack), Powhatan's interest in blue beads, the construction of bridges crossing the various creeks of the bay, and the population of Werowocomoco "by two or three hundred savages."

The Fall of 1608 saw Captain Newport desirous of making Powhatan a vassal of King James. Newport believed this would ensure the Virginia Indian leader’s future cooperation. The Captain arrived from Jamestown "overland to Werawocomoco, some 12 miles.” There he passed the River of Pamaunkee in a “savage canoe" with four men to a reception of dancing, the next day intending to "crown" England's newest ally.

By December of 1608, the English supplies were running short. Needing to obtain more provisions they approached Werowocomoco for corn. Their failure to obtain enough food to sustain the fort at Jamestown convinced John Smith to travel to Werowocomoco. Powhatan agreed to provide the English with food in exchange for a grindstone, fifty swords, guns, beads, chickens, and an English-style house. Four Dutchmen and the Englishman Richard Salvage were sent to Powhatan to construct his new dwelling at year's end. By mid-January 1609 relations between the two parties had grown increasingly distrustful, with rampant insinuations regarding the trustworthiness of the Dutchmen. Some of the English blamed the Dutchmen for inciting the Virginia Indians against the English. Soon thereafter, Powhatan had removed himself, his warriors, and all his valuable provisions to the village of Orapaks on the Chickahominy River.