The graveyard began with a boyhood promise. As schoolmates, Thomas Jefferson and Dabney Carr, his close friend and later brother-in-law, would often go to Monticello Mountain to read beneath the shade of a "great oak." So attached were they to this tree that they pledged that whoever died first would be buried at its foot.
Carr married Jefferson's sister Martha in 1765. He served with Jefferson in the House of Burgesses for a short time and was known as a powerful speaker--Jefferson said that he "was one of the earliest and most distinguished leaders in the opposition to British tyranny." Tragically, Jefferson had to fulfill his boyhood promise when Carr died at the age of 30. To prepare for his burial under the great oak, Jefferson wrote in his garden book, that they “grubbed the graveyard 80 feet square 1/7 of an acre.” The second burial was probably in 1775 of Jefferson’s second child, named after his mother, Jane Randolph, but no stone is left to verify her burial. Jane Randolph herself (d. 1776) was the next burial. By 1782 Jefferson had also buried his wife Martha, and three more children, most likely in the graveyard, although no evidence exists to confirm the children's burial. (Robert H. Kean, History of the Graveyard at Monticello.)
The earliest indications of the physical design of the Graveyard date to 1806, when Jefferson’s garden book indicates a straight route to the graveyard from the house. In 1808, he instructed the farm manager to “plant weeping willows ... around the graveyard exactly on the line of the old paling, and a double row of them on a line with the double row of mulberries from where the mulberries end at the saw pit, down to the graveyard.” In 1885 Jefferson’s great-grandchild, Ellen Wayles Harrison, wrote Prof. A. F. Fleet of the University of Missouri that at the time of Jefferson's death, the graveyard was “enclosed by a double wall filled in between with earth, in which was planted a pyracanthus hedge...” (Robert H. Kean, History of the Graveyard at Monticello.)