Calthorpe was the son of Christopher Calthorpe and Maud Thurton Calthorpe, of Norfolk County, England. He was probably born there and on April 22, 1605, was baptized in Cockthorpe Parish in that county. The family of Calthorpe (also spelled Calthrop) was respectable and well connected. His paternal grandfather was a knight, and he may have been distantly related to Nathaniel Bacon (1620–1692), who became a member of the governor’s Council while Calthorpe was living in Virginia.
Calthorpe arrived in Virginia aboard the Furtherance in 1622. George Sandys, the treasurer of the colony, offered him a room in his house, introduced him to the governor, and advised him how to succeed, but Calthorpe was then only about eighteen years old, and the next spring Sandys wrote of Calthorpe’s inauspicious first months in the colony: “At the first he kept Companie too much with the Inferiours, who hung vpon him while his good liquor lasted.” Calthorpe then spent unprofitable time with “a man of no good example” before joining Thomas Purefoy’s household in 1623 or 1624 in what became Elizabeth City County.
Purefoy, who became a member of the governor’s Council a decade later, may have had a stronger influence on Calthorpe than did Sandys. In 1628 Calthorpe purchased 100 acres of land near Purefoy’s property. Three years later, after the governor and Council opened for settlement the region that became York County, he acquired 500 acres at “the New Poquoson” adjoining a small watercourse later known as Calthorpe’s Creek. In 1636 Calthorpe received patents that secured his title to 1,100 acres in New Poquoson Parish and 100 acres in Warwick County. He named his property Thropland after the family estate in England.
Calthorpe was a captain in the county militia from 1635 to 1648, major by 1652, lieutenant colonel in 1655, and colonel from 1656 to 1661, and he was a justice of the peace from 1652 to 1661. He represented York County in the House of Burgesses in the sessions that met in March and October 1644, Elizabeth City County in the assembly of February 1645, and York County again in the assemblies of November 1645 and March 1646, November 1652, July 1653, and March and October 1660. Although there is no evidence that Calthorpe served as a vestryman, the New Poquoson Parish church was on his property.
Calthorpe’s family life is poorly documented. County records mention his wife, Ann Calthorpe, and indicate that they were married by the mid-1640s. They had at least one son and three daughters. Indentured servants also lived in the household or on Calthorpe’s property, and he relied on tenants to develop sections of his plantation. He lived a longer life than many early immigrants, and his ownership of land and occupation of public offices indicate that he was more successful and more respected than most of his neighbors. Calthorpe did not, however, move into the top rank of colonial society, nor did his children. In that, he was a more nearly typical colonist. Unlike some other planters living in his vicinity during the 1650s, Calthorpe did not replace indentured servants from England with imported Africans or descendants of Africans, although this initial failure to participate in the new labor economy need not necessarily have worked to his family’s economic disadvantage.
In April 1661 the York County Court replaced Calthorpe as a justice of the peace because he had left Virginia, having gone south in search of unsettled land. In a deed executed on January 13, 1662, he identified himself as “Christopher Calthorpe, late of New Poquoson in the county of York in Virginia now of Carolina to the South of Virginia.” Christopher Calthorpe died between then and April 23, 1662, when his widow appointed an attorney to present evidence on Calthorpe’s nuncupative will to the York County Court. The October 1662 inventory of his estate, which was valued at 30,480 pounds of tobacco and cask, showed that five tenants then lived on his property. Calthorpe’s house had at least two well-furnished rooms, his farm had a shed, he owned several draft oxen, and corn and tobacco were growing in his fields. He also owned one or more beehives, on which the appraisers did not set a value.