Caroline County was named for Caroline of Anspach, consort of George II. It was formed from Essex, King and Queen, and King William Counties in 1728, and additional parts of King and Queen were added in 1742 and 1762.

Most loose records and deed books prior to 1836 and will books prior to 1853 were stolen, mutilated, and/or destroyed by Union troops who ransacked the courthouse in May 1864. A near-complete run of order books exists.

In 1780 the Virginia General Assembly replaced the Anglican vestries and churchwardens of the colonial period with elected bodies called Overseers of the Poor. The Overseers provided food, clothing, shelter, and medical treatment for the persons who were too poor to support themselves or too ill to provide for their basic needs. They also bound out children whose parents could not support them or who failed to educate or instruct them, as well as orphans to become apprentices. The boys learned a trade and the girls learned domestic skills.

In 1844, the General Assembly enacted laws to create poor farms overseen by boards of directors for the maintenance and education of the poor. The boards bought farms and built buildings, appointed a superintendant for each poor farm, and chose a physician to attend the sick and teachers to educate the children. The adults and older children were required to work if they were able.