Upper Marlboro was a small tobacco town on the western branch of the Patuxent River in Prince George’s County, Md., about halfway between Annapolis and Mount Vernon. In 1775 it was described by a visitor as “a very pleasant” place, “containing about a Dozen very neat houses & 3 or 4 stores” (HONYMAN description begins Philip Padelford, ed. Colonial Panorama 1775: Dr. Robert Honyman’s Journal for March and April. San Marino, Calif., 1939. description ends , 4).

Atty. Gen. John Randolph of Williamsburg and Edmund Pendleton (1721–1803) of Caroline County were retained by GW about this time to act with James Mercer of Fredericksburg as attorneys for the Custis estate in a suit that was apparently to be heard in the General Court at Williamsburg between 10 and 15 Oct. The case involved an old claim against the family for payment of a substantial sum of money allegedly owed to descendants of an illegitimate daughter of Daniel Parke (1669–1710), Jacky and Patsy Custis’s great-grandfather. That dispute, which had been going on for more than 50 years, would continue for at least a few more years, but the plaintiffs would never obtain a final judgment in their favor (General Ledger A description begins General Ledger A, 1750–1772. Library of Congress, George Washington Papers, Series 5, Financial Papers. description ends , folio 345; FREEMAN description begins Douglas Southall Freeman. George Washington: A Biography. 7 vols. New York, 1948–57. description ends , 2:281–91, 298–301, 3:225–27, 282, 335).

John Randolph had attended the races in Annapolis with his daughters, traveling there on board the armed schooner Magdalen (Va. Gaz., P&D, 17 Sept. 1771).