This paper employs data from selected sample survey areas in the northern Fertile Crescent to demonstrate how initial urbanization developed along several pathways. The first, during the Late Chalcolithic period, was within a dense pattern of rural settlement. There followed a profound shift in settlement pattern that resulted in the formation of large walled or ramparted sites ('citadel cities') associated with a more dynamic phase of urbanization exemplified by short cycles of growth and collapse. By the later third millennium BC, the distribution of larger centres had expanded to include the drier agropastoral zone of northern and central Syria, termed here the 'zone of uncertainty'. This configuration, in turn, formed the context for Middle Bronze Age settlement, and the pattern of political rivalries and alliances that typified the second millennium BC. Evidence is marshalled from archaeological surveys and landscape analyses to examine these multiple paths to urbanization from the perspectives of (a) staple production within major 123J World Prehist (2014) 27:43-109 DOI 10.1007/s10963-014-9072-2 agricultural lowlands; (b) the shift towards higher risk animal husbandry within climatically marginal regions; (c) changes in local and inter-regional networks (connectivity); and (d) ties and rights to the land. Textile production forms the core of the proposed model, which emphasizes how the demand for wool and associated pasture lands opened up new landscapes for agro-pastoral production and settlement. The resultant landscapes of settlement are then compared with the picture in the southern Levant where a more restricted zone of uncertainty may have limited the opportunities for agro-pastoral production.