Reverend Horace Holley, a New England-born, Yale-educated, Unitarian minister from Boston, was offered the presidency of Transylvania University in the town of Lexington, Kentucky, in 1817. He investigated the opportunity by way of a "tour of inquiry," a circuitous route west through notable "literary establishments" of the east. His purpose was to learn the character of higher learning--the content, expectations, uses, and structures of America's colleges--in anticipation of his start at Transylvania. This article interprets Reverend Horace Holley's reflections as part of a larger narrative of academic self-identity and therefore sits at the intersection of two distinct yet complimentary historiographic traditions, biographies of early college presidents and the history of American professionalism.