The castle, which likely stood on or near the present site of the now demolished Castleforward House, was held by the O’Doherties clan in 1440 before meeting its first destruction in 1529. Following its dismantling, the O’Donnell family took possession of the site, continuing the pattern of ownership amongst Gaelic Irish nobility that characterised much of medieval Ulster.

The castle’s tumultuous history continued into the early 17th century, when records indicate it had fallen into disrepair by 1600, only to be restored the following year. This renovation proved timely, as English forces established a garrison there in 1610 during the period of increasing Crown control over Ulster. The castle’s military significance appears to have been short lived, however; it was likely demolished entirely during the 17th century, possibly as part of the widespread destruction that accompanied the various conflicts of that era.

Today, visitors to Castleforward Demesne will find scant physical evidence of this once significant fortification. Archaeological surveys conducted by Davies and Swan in 1939 noted several stones that may have originated from the castle, though only one stone, embedded in a wall beside what was then Castleforward House, could be definitively located during later investigations. Even this tenuous link to the past has since been compromised, as Castleforward House itself has been razed to the ground, leaving only historical records and archaeological notes to tell the tale of this vanished stronghold.