This strategic riverside location, combined with the area’s notably fertile agricultural land, made it an obvious choice for settlement long before the Ulster Plantation. The O’Donnells recognised its importance in the fifteenth century when they built a castle here, though technically just across the border in what’s now County Tyrone. The site changed hands multiple times during the turbulent late 1500s; the Earl of Essex arrived in 1574 during his disastrous Ulster expedition, whilst Sir Henry Dowcra’s forces finally captured it for the English Crown in 1600. By then, there was already a substantial settlement of about eighty houses surrounded by an old ditch, significant enough that Dowcra secured market rights for the town in 1603.

The real transformation came with Sir Richard Hansard, who received a grant for the village in 1611 on condition he settle sixty inhabitants within five years, though this requirement was later halved to thirty English or Scottish tradesmen. Hansard threw himself into developing the town with remarkable enthusiasm, constructing twenty-one half-timbered houses in the English style and thirty-seven single-hearth cottages by 1611. The town boasted impressive fortifications; a substantial fort built of lime and stone with bulwarks, parapets and a deep ditch, plus a smaller fort that housed the gaol. When Pynnar visited that same year, he found a thriving community of English, Scottish and Irish inhabitants practising various trades. By 1622, Lifford had grown to at least fifty-four houses with about one hundred male residents, making it one of Ulster’s more successful plantation towns. Hansard’s dedication to his creation extended beyond his death in 1619; his will left provisions for the corporation, a church, a school, and salaries for the schoolmaster and town officers.

The town’s layout centred on the Diamond, with the main street running southwest towards the ferry crossing that preceded the modern bridge. The market, held weekly on Mondays from 1612, took place in the Diamond, whilst burgage plots along the northwestern street possibly housed those original cottages from 1611. Archaeological work in the 1990s revealed that the River Foyle has been considerably narrowed since the plantation period, with excavations behind the courthouse uncovering sands and gravels that suggest the river once flowed much closer to the town centre. Though the defensive ditch shown on a 1600 map has long since vanished, Lifford remains a fascinating example of plantation town planning, where English colonial ambitions met Irish geography to create something uniquely Ulster.