Charles City County originally included land on both sides of the James River, and the name of City Point near the mouth of the Appomattox River is a residue of those boundaries
Source: Library of Congress, A new map of Virginia, Maryland, and the improved parts of Pennsylvania & New Jersey (1685)
Counties were not planned in advance to be part of the English settlement in Virginia in 1607. The new colony was a private company's investment, and was governed by the stockholders of the company until it went bankrupt and the charter was revoked by King James II.
Government in Virginia, including the formation of counties and cities, evolved in reaction to unplanned events. In 1607, there was no expectation that the venture capitalist's investment in a foreign land would result in "government of the people, for the people, by the people." Democracy was not imported into Virginia on the Susan Constant, Godspeed, and Discovery.
The Virginia Company of London was managed by a council in London, orginally appointed by King James I. The company sent its colonists to the New World without even announcing who would be the local leaders in Virginia. When the Susan Constant, Godspeed, and Discovery finally reached the James River, Captain Newport opened the sealed envelope with the London Company's instructions - and had to release Captain John Smith from confinement, so that prisoner could take his place on the resident council.
Until 1624, the colony of Virginia was a business managed by the equivalent of a plant manager (the "president" of the council, then the "governor") with a local oversight board (the council, then the General Assembly). The company's "Board of Directors" was the London Company lead by its Treasurer, and those directors remained in England.
Management from the other side of the Atlantic Ocean was weak, while conflict among members of the local council in Jamestown was intense at times. In the early days of Jamestown, one local member of the council was executed as a Spanish spy while John Smith was threatened with execution by his Council rivals. The explosion of his gunpowder pouch in 1609 while he slept, which damaged his thigh and caused him to return to England in October, may have been an assassination attempt rather than an accident. Leadership in the colony was never easy.
To attract settlers after the "starving time" in 1609-10 and the failure of the colony to thrive, the London Company offered potential investors a great deal of flexibility in creating new settlements. Shiploads of settlers were sent to Virginia to create largely self-sufficient "hundreds." The name reflected the anticipated number of new settlers required to establish a permanent community. These new hundreds were required to be at least several miles from any existing community, and Bermuda Hundred became a famous place name on the James River during the Civil War.
Within the London Company, there were internal disputes between investors who wanted to maintain strict discipline over colonists as reflected in the "Laws Divine, Morall and Martiall." The faction led by Thomas Smythe finally lost control to the group led by Edwin Sandys, and in 1618 the company adopted the Great Charter. The new group sent a new governor, Sir George Yeardley, to Virginia with the intention of making the place attractive to new settlers, in part by granting greater freedom and in part by sending more women across the Atlantic so English families could be established in Virginia.
In the 1618 instructions to George Yeardley (the Great Charter) issued by the Virginia company in 1618, the colony was divided into four parts called "incorporations" - Henricus, Charles City, James City, and Kecoughtan. That same year, King James I granted the Third Charter with provisions for elected representatives to help govern the colony.1
In 1619 the 11 small settlements elected representatives to the first General Assembly; representation was not based on the boundaries of the four Incorporations. In addition to those 11 settlements, there were also "particular plantations" outside the direct control of the London Company. That first General Assembly in 1619 rejected representatives that were elected from Martin's Brandon, in today's Prince George County, because that particular plantation was not obliged to comply with whatever decisions wre made by the General Assembly.2
the 1907 Memorial Church on Jamestown Island was built on top of the foundations of the 1617 church in which the General Assembly first met
Starting with the 1619 meeting, the General Assembly handled executive, legislative, and judicial issues for the Virginia colony. The assembly created the first local courts to handle small lawsuits in 1622.3
After the Native American uprising of 1622, it was clear that the Virginia colony would never be profitable. The colony might be an outpost of English culture and government in the New World, but the stockholders would not get a good return on their investment. In 1624, King James I took official control of Virginia by revoking the London Company's charter. The General Assembly continued to meet after King James I assumed control.
Between 1624 and the American Revolution, Virginia was ruled as a royal colony of the king. In contrast to Maryland and Pennsylvania, Virginia was never a proprietary colony where authority was granted to an individual such as William Penn or Lord Calvert.
The population increase to about 5,000 colonists in 1634 caused the General Assembly's administrative workload to become a hassle. Population growth of the colony triggered a need for official decisions that were local and not of concern to the entire General Assembly, or appropriate to delay until the next session.
In 1634 the elected legislature, with the approval of the appointed royal governor, chartered eight units of local government. Local officials, appointed by the General Assembly, were expected to handle more responsibilities beyond the minor legal disputes already being resolved by local courts started in 1622.
The term "shires" was used in the original act. Since then, those local governmental units have been described as "counties" - but the key law enforcer in most county governments is still known as the sheriff (derived from shire reef).
The eight new jurisdictions, which were commonly called "counties" rather than "shires," included the four existing Incorporations of Henrico, Charles City, James City, and Elizabeth City. Elizabeth City replaced the "heathen" name of Kecoughtan, and is now part of the City of Hampton. Four new counties were also incorporated: Accomack, Charles River (renamed York in 1643), Warrosquyoake (renamed Isle of Wight in 1637), and Warwick River (now part of Newport News).
The boundaries of future counties were drawn and then modified so most landowners in that jurisdiction could reach their county court sessions, where justices dealt with property issues and criminal accusations, in one day. County boundaries would be defined and altered until the last county of Virginia (Dickenson) was created in 1880, but the primary basis for drawing Virginia's county boundaries was to make the courts accessible.