James Pittillo (b. 1690-1698 Scotland - d. 1754 Dinwiddie County, Virginia) was a Scots laborer and Jacobite rebel, who became a major landowner after being deported in 1716 to the Colony of Virginia. After completing service of his indenture, in 1726 Pittillo was granted 242 acres (1.0 km2) on Wagua Creek in Brunswick County, Virginia.
Appointed as a tobacco inspector in Bristol Parish in 1728, that year he was also selected for the major expedition of William Byrd II to survey the border between Virginia and North Carolina. Through grants of headrights and purchases, Pittillo eventually acquired more than 4,000 acres (16 km2) in the area of what developed as Prince George, Brunswick, and Dinwiddie counties in Southside Virginia.
James Pittillo was born between 1690 and 1698 in Scotland, likely in Perthshire. According to records in the British Archives of persons captured in the Jacobite rising of 1715 and deported to the colonies, James Pittillo was a laborer from the parish of Logierait in the ancient county of Perthshire (or Perth). Pittillo was captured at the Battle of Preston, tried, and transported on the ship Elizabeth and Anne to Virginia in June/July 1716.
James settled in Bristol Parish, Prince George County. This was part of what became known as Southside Virginia. His name first appeared in colonial Virginia records in February 1723/24 when he witnessed the will of Richard Smith. In April 1724, Pittillo was recorded as surveying 200 acres (0.8 km2) on the north side of Moccosoneck (presently called Rowanty) Creek in Prince George County, Virginia.
In October 1726, having served his indenture to pay for the costs of his transportation to the colony, Pittillo was granted 242 acres (1.0 km2) on Wagua Creek in what was now Brunswick County. (The county was formed in 1720, partly from land previously assigned to Prince George County.) In 1734, Pittillo received a grant for 844 acres (3.4 km2) on both sides of White Oak Swamp of Rowanty. In 1735, he was granted 252 acres (1.0 km2) on Sturgeon Run, land which he sold in 1742.