This paper provides background to the various road transport routes between Grafton on the North Coast and the Northern Tablelands of New South Wales and why the Grafton-Glen Innes line was eventually chosen. The development of the Grafton-Glen Innes link and its evolution through to the contemporary line are discussed along with some unique circumstances and events of that period. Not only was local competition active among towns vying for direct road links, but also competing with the burgeoning rail network, expanding throughout NSW. Eventually rail won out and remained the dominant form of land transport in the area well into the 20th century. However, that win had some losses in other areas, resulting in change to town and population dynamics and patterns of settlement.