Cheesman was born in Virginia, probably in what is now York County and probably a year or two after the marriage in the mid-1640s of his father, Edmund Cheesman (d. by 24 February 1674), to a widow, Mary Lilley, whose maiden name is not known. She had at least one son at the time of the marriage. Contemporaries spelled his surname in a variety of ways, the most common being Chisman, and some records mistakenly refer to Cheesman and his father by the given name Edward. His father and two uncles, including(d. by 2 May 1665), who served on the , emigrated from England and patented land on Poquoson Creek and what was later known as Chisman Creek in York County. In spite of a decree the General Assembly had issued, in 1661 Cheesman’s mother apparently involved her husband, “his said negroes & whole family” in an illegal Quaker meeting.
Cheesman married late in the 1660s and had one son, who died at age ten. His wife’s given name was Lydia, and her maiden name may have been Farloe or Farlow. Her stepfather was probably a Quaker, and it is possible that she also followed that religion. Cheesman patented about 200 acres of land in York County on July 8, 1670, and on July 25 became a justice of the peace. He attended court sessions regularly, was a captain in the York County militia by 1672, and four years later became a major. When Bacon’s Rebellion began in the summer of 1676, Cheesman supported Nathaniel Bacon. His father had marched against the Pamunkey Indians in 1644, and Cheesman may have embraced Bacon’s plans to make war on Virginia’s Indians, but his wife later asserted that she bore responsibility for his choice. His wife’s uncle also supported the rebellion and later was hanged.
Cheesman’s role in Bacon’s Rebellion is sparsely documented, but he was described as one of the principal actors. Captured in York County in November 1676, about a month after Bacon’s death, Cheesman was accused of treason. His wife contrived to be present when Governor Sir William Berkeley questioned him, and she pleaded with the governor to spare her husband’s life on the grounds that “if he had not bin influenc’d by her instigations, he had never don that which he had don.” On “her bended knees” she begged the governor “that shee might be hang’d, and he pardon’d.” Her eloquence and bravery failed to persuade the governor to release or spare him, but before his trial could take place, Edmund Cheesman “dyed in prisson, of feare, Greife, or bad useage.” The date of his death is not recorded. Berkeley’s proclamation of pardon, issued on February 10, 1677, exempted several men, including Cheesman, who were already dead and declared that they were to be adjudged convicted and attainted of high treason as though they had been tried. In April 1678 Lydia Cheesman claimed her husband’s estate, which consisted of 250 acres in York County, six laborers (five black, one white), livestock, and household furnishings. She married Thomas Harwood in June of that year and lived until the spring of 1695.