This paper explores the complex attitude towards the classical past in Dionysius’ critical writings along with the ways in which connecting with and experiencing the past is bound up with classicist practices of reading and writing. The classical past for Dionysius is not the historical Athens of the fifth and fourth centuries BC but a structure of feelings encoded in and experienceable through the classical texts. The ‘classical’ thus becomes transferable to Augustan Rome where it forms the basis for the creation of a ‘classical’ present and future. At the same time, Dionysius is acutely aware of the gap separating his experience of the classical texts from that of their original audience. It is the continuous (but ultimately never successful) attempt to close this gap and to achieve some sort of an ‘original’ experience of the classical texts that is the driving force behind classicism as a cultural practice.