At Pompeii, like many Roman cities, there is a broad thoroughfare that cuts a wide and direct course across the space of the city. The via Stabiana, or via Pumpaiiana as its Oscan name might have been, runs diagonally across the middle of a southward sloping plateau jutting out from the base of Mt. Vesuvius, connecting the Porta Vesuvio to the Porta Stabia. More than dividing Pompeii roughly in two, via Stabiana cuts through the entire history of the ancient city and served witness to its development from the archaic era until its violent destruction in 79 CE. This paper takes this long-lived route as a means to delve into the evolving landscape of an ancient urban street, beginning with via Stabiana’s role within the development of Pompeii’s street network, as different grid systems grew up around and eventually incorporated it. The focus next narrows to the variety of surfaces that covered the street – the pavements made of beaten ash, lava stone, and even post-earthquake(s) debris – as well as the architectures that surrounded it, such as the curbstones that separated vehicles and pedestrians and the steeping-stones that permitted both pass unimpeded through intersections. What we know of the volume of traffic and even the particular directions these vehicles and pedestrians took are then examined, setting up a discussion of the need for street repair and the surprising manner in which the Pompeians accomplished this just before the city’s internment: by pouring molten iron and iron slag into holes in the pavements and onto its deepest ruts.