Origin of the Name "Monticello"
From Thomas Jefferson Encyclopedia
The exact source of the word "Monticello" (pronounced as Monti-cello like the musical instrument) as the name for Jefferson's plantation home remains a mystery. Jefferson's earliest documented use of the word appears in his Garden Book entry of August 3, 1767: "inoculated common cherry buds into stocks of large kind at Monticello." Yet just two years later in his Account Book Jefferson records that 9787 pounds of tobacco were made at "Moncello" in 1768. Then in a January 1770 entry of his Account Book Jefferson notes "work to be done at Hermitage," but at some point, he crosses Hermitage out and writes in Monticello. After this last entry, Jefferson consistently refers to his property as Monticello, but because these early entries may have been made retroactively, it is impossible to pinpoint exactly when Jefferson began to use the name.
Since Monticello means "hillock" or "little mountain" in Italian, there is a logical explanation for Jefferson's choice. He could have translated into Italian the names that appear in Albemarle County Deed Books as Little Mountain and High Mountain, the latter becoming Montalto, a mountain to the southwest of Monticello that Jefferson acquired in 1777. Jefferson's interest in Italian began as early as 1764 when he purchased an Italian-English dictionary, two historical works in Italian, and the works of Machiavelli. By 1767 Jefferson had also convinced Francesco Alberti, a musician from Faenza, to move into the area so that he could study the violin with him.
Another source may have been Andrea Palladio's Four Books of Architecture, a work Jefferson deemed to be his "bible." In Book Two of the 1721 Leoni translation that Jefferson refers to in the account books of the 1770s, Palladio describes the ideal setting for a country house, his famous Villa Rotunda near Vicenza: "Its situation is as advantageous and delicious as can be desired, being seated on a hillock of a most easy ascent." Whether or not Jefferson read this in Italian at this early date is unclear, but it is a possibility. At least the theater-like description of the site, located on top of a hillock above a navigable river and surrounded by hills and orchards, must have influenced Jefferson.
Because Jefferson knew Italian and himself named Monticello, it seems apparent that he would have used the Italian pronunciation. The name has been used elsewhere in the United States and Americanized into "Montisello," but there is no contemporary evidence to support this pronunciation. We do not have anything in Jefferson's writing that tells us how he pronounced the word, but we have other written records that indicate the Italian pronunciation. For example, in 1781 George Gilmer writes to Jefferson, "I long to behold the period when you may with propriety retreat to Montichello." In 1843 James Adams Kasson, a newcomer to Albemarle County who becomes acquainted with a member of the Jefferson family, writes: "I am working my way around . . . into most of the families of this circle which contains, besides those I have before mentioned, a gentleman closely related to Jefferson and brought up at Monticello (President J.'s seat), the 'c' pronounced like 'ch' in chair -- 'Montichello.'"