The concern of this paper is with the towns of Pella/Fihl, Gerasa/Jarash and Philadelphia/Amman, all located in modern Jordan, during early Islamic times. A long-established road linked these three towns, striking eastwards from Fihl up the Jordan Rift scarp into the highlands of Jordan, eventually reaching the regional capital of Amman. Unlike the route between Qaysariyah and Baysan, the Fihl – Amman road is not described by any of the third/ninth and fourth/tenth century Arabic geographical sources, but archaeologically there is little doubt that this route was active, to varying degrees, in the early Islamic period. The paper investigates the urban nature of these towns at that time, and in what ways these centers differed from their late antique predecessors of, say, the mid-sixth century CE, beginning with Pella/Fihl and then continuing eastwards to Jarash and Amman, and finishing with a reflective look at Skythopolis/Baysan