Though much of this natural moat has since been reclaimed, the strategic brilliance of the location remains evident. The castle first appears in historical records in 1587, when the lands were granted to Sir John O'Doherty, and by 1601 it had grown into a formidable stronghold. Contemporary accounts describe it as the chief seat of the O'Doherty clan, complete with thick ramparts, two casemates and five pieces of artillery defending what was essentially a peninsular fortress.

The castle's turbulent history reflects the wider upheavals of early 17th century Ulster. After brief occupation by English forces in 1601–2, it was returned to Cahir O'Doherty, only to be seized again following his failed revolt in 1608. The subsequent Plantation of Ulster saw the estate leased to Thomas Chichester, who by 1611 had rebuilt the castle, adding a substantial stone house within the bawn and two timber structures outside it. The property later passed to Sir Charles Chichester and likely remained inhabited until around 1690, after which it began its slow decline into ruin.

Today, visitors can still trace the bones of this once mighty fortress, though time has not been kind to its fabric. The keep was already roofless by 1833, and many windows were destroyed in the 1890s, with some demolition occurring even earlier in the 19th century. The extraordinary defensive fosse that once ringed the hilltop, still impressive in the 1830s and traceable as late as 1938, has now been almost entirely ploughed out, surviving only as a slight depression in the landscape. A small section of bank incorporated into modern field walls southwest of the keep may be all that remains of the original enclosing rampart, a humble remnant of what was once one of Ulster's most strategically positioned strongholds.