Its importance was recognised long before the plantation era; the O’Donnells built a castle here in the fifteenth century, though this structure actually stood on the Tyrone side of the river. Throughout the 1500s, various English expeditions eyed this location with interest. The Earl of Essex arrived in 1574 during his doomed Ulster campaign, whilst Perrott proposed establishing an English garrison here a decade later. It wasn’t until 1600, when Niall Garbh O’Donnell captured it for Dowcra’s forces, that the English finally gained control. By then, a modest settlement had already formed around the fort, described by contemporaries as “some eighty houses set in a plain green upon the river side and encompassed by an old ditch”.

Following the Flight of the Earls, Lifford was earmarked for plantation. In 1611, Sir Richard Hansard received the village, its fort (known as Captain Brooke’s Fort), and roughly 500 acres of land. His grant came with conditions: within five years, he needed to allocate plots to sixty inhabitants for houses and gardens, plus set aside 200 acres as common land. These requirements were soon relaxed; by 1612, he only needed to settle thirty English or Scottish tradesmen as burgesses, though he also had to reserve 100 acres for keeping fifty horses should the Crown decide to garrison the town. Hansard threw himself into developing Lifford, constructing twenty-one half-timbered houses and thirty-seven single-hearth cottages by 1611.

That same year, the surveyor Pynnar painted a vivid picture of Lifford’s fortifications and emerging community. He described a substantial stone fort with bulwarks, parapets, and a deep ditch on the riverside, complete with storehouses, a gatehouse, and drawbridge. A second, smaller fort existed somewhere in the town, surrounded by English-style timber houses that served as a jail and gaoler’s quarters. The town itself bustled with English, Scottish, and Irish inhabitants pursuing various trades. Today, nothing remains of these impressive fortifications that once guarded this crucial river crossing. A contemporary plan of “the king’s fort at Lifford” survives in Trinity College Dublin’s library, offering a glimpse of what once stood, whilst the exact location of the second fort mentioned by Pynnar remains a mystery.