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- May 4 - While exploring the James River, the English party first make contact with the Paspahegh, enjoy a feast with them, and listen to, but are unable to understand, an oration by the Paspahegh weroance, Wowinchoppunck.
- May 14 - The English begin their occupation of Jamestown Island, an island in Paspehegh territory where Indians sometimes camped, though without any permanent habitations. The English begin building a defensive fort on the island; a few Paspehegh braves paddle in on canoes around midnight to investigate what they are doing, but flee when the English watchman sounded the alarm. A few days later, two well-dressed and highly decorated Paspehegh messengers arrive at the fort to announce that their weroance would soon be paying them a visit, and bringing a "fat Deare" with him.
- May 18 - Wowinchoppunck and one hundred armed men visit Jamestown fort. According to George Percy's 1608 account, Wowinchoppunck indicated that he would grant the settlers "as much land as we would desire to take," although it is highly dubious that he would have said any such thing, according to later historians. The Paspaheghs leave in anger after a violent dispute over an English hatchet.
- May 19 - Percy and 3 or 4 others explore the woods on foot and discover a nearby Paspahegh village; they receive gifts of tobacco, but return to the fort quickly after they see an armed brave suddenly plunge into the woods, probably to notify Wowinchopunk.
- May 20 - Forty Paspahegh braves arrive at the fort with a deer for feasting; they engage in target practice for the English, demonstrating that their bows were capable of piercing wood, but not steel.
- May 26 - While half of the English party is away with Captain Newport exploring upriver in Weyanoke, Appomattoc, Arrohattoc and Powhatan territory, a combined force of 400 Paspaheghs, Quiockahannocks, Weyanokes, Appomattocs and Chiskiacks assault the fort, but withdraw upon receiving English gunfire; at least 3 Indians and 1 colonist are killed, with several wounded on both sides. Indian raiding and harassment continues for a week or two thereafter as the English hasten to complete their fort.
- June 15 - The paramount chief Powhatan (Wahunsunacock) announces a ceasefire, causing Paspahegh raids to cease abruptly.
- November - The Paspehegh return an English boy who had run away, confirming their intentions are no longer hostile. Faced with starvation, the settlers turn to the neighboring tribes, including the Paspehegh, for help, buying small amounts of corn from them on three occasions. However, John Smith wrote of one of these occasions in ungrateful terms, calling the Paspahegh a "churlish and treacherous nation."
- December - While exploring the Chickahominy country, Smith stumbles upon a huge communal hunting party of several Powhatan subtribes, including the Paspehegh, being led by Opechancanough, brother of the paramount chief Powhatan. Smith is captured and taken around Powhatan territory as an involuntary guest, eventually meeting the paramount chief himself, who orders the English to leave Paspahegh territory and instead take up residence at Capahosic, a satellite village near his own capital Werowocomoco, where he would provide them food and security in exchange for metal tools. Smith promises to comply, and is released on January 1, 1608.
- Spring, 1608 - An uneasy alliance concluded with chief Powhatan in the winter — during which time he saved the English from starvation by sending them regular supplies of corn — begins to fall apart, when the English are seen to be conducting military drills outside their fort in the Spring. Paspahegh harassment and filching tools at the fort then resumes, causing the English to take eight of them prisoner; the Paspahegh responded by taking two Englishmen who wandered outside the fort as their own prisoners. The same night, the colonists escalated hostilities, raiding and burning the nearby Paspahegh villages. At this, Wowinchopunk released the two Englishmen, but the English only released one Paspahegh, keeping the rest until chief Powhatan sent a gift of corn along with his own young daughter, Pocahontas, to plead for their return.
- Fall, 1608 - Again faced with starvation, the English try to buy corn from their neighbours, but find them less willing to sell, being particularly antagonized by Captain Newport's mock coronation of paramount chief Wahunsunacock as a supposed "vassal" of King James I, then leading a military expedition to the Monacan country, against the chief Powhatan's wishes. The Paspeheghs and most other tribes along the James abandoned their villages and hid when the English came to buy corn that fall, and only a few natives were found whom they could force at gunpoint to sell their corn.
- Spring, 1609 - Harassment by the Paspaheghs and other groups continues at the fort; in one skirmish, the weroance Wowinchopunk himself is captured by John Smith, at the time President of the colony. He eventually escapes, at which Smith raids his town, stealing two canoes, and killing six at another town. Wowinchopunk (through his orator, Ocanindge) later makes peace, but stating that if the English use further force against him, he will abandon them to starve, and telling Smith "We perceive and well knowe you intend to destroy us, that are here to intreat and desire your friendship..."
Several colonists are boarded in Indian towns in the following truce, but relations remain strained, and the truce again falls apart when Smith tries unsuccessfully in the summer to establish further English fortifications in the territory of the Nansemond tribe (who lived downriver) and the Powhatan proper (who lived upriver around what is now Richmond, Virginia). Smith left Virginia in October 1609, but that same month the colonists did succeed in establishing an English fort (Fort Algernon) in the territory of the Kecoughtan tribe (near modern Hampton, Virginia).
- May - After a particularly harsh winter in which many English died of starvation, Sir Thomas Gates arrives with more colonists, provisions, and orders from King James to "christianize" the Indians, which at that point seemed hardly feasible, given the hostile and abusive relationship between them up to that point. After taking a look around, Gates decided to evacuate the colony, and Jamestown was abandoned. The day after setting sail, they encountered the remainder of Lord De la Warr's fleet coming into the Chesapeake bay — which had left England a year earlier, but become lost in a hurricane. They therefore returned to the fort under Lord De la Warr's command.
- July - The nobleman, Lord De la Warr, proved far harsher and more warlike toward the Indians than any of his predecessors, and his solution was simply to engage in wars of conquest against them, first sending Gates to drive off the Kecoughtan from their village on July 9, then giving chief Powhatan the ultimatum of either returning all English subjects and property, or facing war. Powhatan responded by insisting that the English either stay in their fort, or leave Virginia. Enraged, De la Warr had the hand of a Paspahegh captive cut off and sent him to the paramount chief with another ultimatum: Return all English subjects and property, or the neighboring villages would be burned. This time, Powhatan did not even respond.
- August 9, 1610 - Tired of waiting for a response from Powhatan, Lord De la Warr sent Percy with 70 men to attack the Paspahegh capital, burning the houses and cutting down their cornfields. They killed 65 to 75, and captured one of Wowinchopunk's wives and her children. Returning downstream, the English threw the children overboard, and shot out "their Braynes in the water". The queen was stabbed to death in Jamestown.
The Paspahegh never recover from this attack, and abandon their town. This attack, and the offense of killing royal women and children, ignites the First Anglo-Powhatan War.
- February 9 - In a skirmish near the Jamestown fort, Wowinchopunk is mortally wounded. Soon thereafter, his followers avenge his death by luring several colonists out of the fort and killing them. However, the bulk of the broken tribe appear to have merged with the other chiefdoms, and they disappear from the historical record at this point. Subsequent use of the word Paspahegh in documents is mainly in reference to their former territory.
- May 21 - Sir Thomas Dale, Lord de la Warr's new replacement, visits the site of the former Paspehegh capital and finds it overgrown with weeds.
The original capital of the Paspahegh Indians, Sandy Point in Charles City County, Virginia, was settled by the English in 1617 as Smith's Hundred. After 1619, it was known as Southampton Hundred. St. Mary's Anglican Church was established there prior to the Powhatans' Uprising of 1622.
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