In his study of the historical geography of early modern Ireland, William J. Smyth recognized the central role of towns and villages in the transformation of the cultural and social landscape of Ireland during British settlement in the sixteenth and seventeenth centuries. The changes wrought by these urban settlements can be observed most acutely in Ulster where, from the early seventeenth century, officials made preparations for a plantation. Towns and villages became a core feature of the conditions for plantation, with twenty-five corporate towns proposed in the plan. The plantation conditions also instructed undertakers of the largest estates to encourage clustered village settlement on their lands. These towns and villages had a dramatic effect on the social and cultural landscape of the province, with the emergence of an urban network built and governed in the same fashion as early modern towns in England.

By 1641, Ulster had a significant urban geography with sixteen of the twenty-five towns proposed under the plantation fully incorporated, and large numbers of towns and villages scattered across the plantation network as a whole. In County Donegal, for example, four towns – Ballyshannon, Donegal, Killybegs and Lifford – had received their charters, while significant market towns had developed at Letterkenny and Raphoe. While County Donegal is geographically a large area, the emergence of such a large town network from the north to the south suggests just how significant the urban spread was in Ulster in the aftermath of plantation.

It is not surprising, therefore, that at the outbreak of rebellion in October 1641, these towns became the focus of rebel attacks. Towns and fortified settlements such as Dungannon, Charlemont, Mountjoy, Cookstown, Moneymore and Dungiven were among the first locations to fall into rebel hands in Ulster.