Thomas Jefferson was an avid book-collector, a voracious reader, and a gifted writer, a man who prided himself on his knowledge of classical and modern languages and whose marginal annotations include quotations from Euripides, Herodotus, and Milton. And yet there has never been a literary life of our most literary president. In The Road to Monticello, Kevin J. Hayes fills this important gap by offering a lively account of Jefferson's intellectual development, focusing on the books that exerted the most profound influence on his writing and thinking. Moving chronologically through Jefferson's life, Hayes reveals the full range and depth of Jefferson's literary passions, from the popular "small books" sold by traveling chapmen, such as The History of Fortunatas and The History of Tom Thumb that enthralled him as a child, to his lifelong love of Aesop's Fables and Robinson Crusoe, his engagement with Horace, Ovid, Virgil and other writers of classical antiquity, and his deep affinity with the melancholy verse of Ossian, the legendary third-century Gaelic warrior-poet. Drawing on Jefferson's letters, journals, and commonplace books, Hayes offers a wealth of new scholarship on the literary culture of colonial America, identifies previously unknown books held in Jefferson's libraries, reconstructs Jefferson's investigations of such different fields of knowledge as law, history, philosophy, and natural science and, most importantly, lays bare the ideas which informed the thinking of America's first great intellectual.