The first stone castle in Killorglin was built on the instruction of Maurice FitzGerald in 1215AD as part of a line of frontier defences on the Laune and Maine river valleys.

Geoffrey de Marisco, the King’s justiciar in Ireland, gained control of the Manor of Killorglin from the outset, holding it until his death in 1245.

The McCarthys destroyed Killorglin Castle in 1261 following their victory at the Battle of Callan. It was easily rebuilt as ‘destruction’ was usually symbolic – burning the wooden floors to make the building uninhabitable and demolishing the battlements to render it undefendable. The McCarthys destroyed the outpost again in 1280, by which time a small village had grown up on the Dromavally side of the river.

The Earl of Desmond was created in 1329 and the McCarthys became vassals of the FitzGeralds, residing in Killorglin Castle until the 1580s, when the castle was destroyed at the beginning of the Second Desmond Rebellion.

Jenkin Conway was granted the Castle in 1587 under the terms of the Plantation of Munster. The Irish name for the hillock ”Cnocán na gCeap” – on which the fortification was rebuilt – means “the Little Hill of the Stockade”.

During the Nine Years War (1894-1603) most Elizabethan settlers left Munster; not so Jenkin Conway who remained in Killorglin. He was physically removed – at sword point –  from his home in 1600 by Finín McCarthy who burned the Castle to the ground but spared the Conways.

For the remainder of the 17th century the Conways and their successors (ca. 1690), the Blennerhassetts, lived at Reen Lodge, near Ballykissane Cross.

Captain John “Black Jack” Blennerhassett supported the Williamite Cause in the 168801690 War and returned to Killorglin after the victory at the Boyne in July 1690. He rebuilt the family mansion in the late 1690s/early 1700s, naming it “Castleconway” – which was also the name of the village/town for the next 100 years or so.

Harman Blennerhassett sold Killorglin to Thomas Mullins in 1795. Mullins became Lord/Baron Ventry in 1800, leasing Castleconway House to various tenants. Fr. James Luony PP, Killorglin was the last resident in the building, where he died in 1844.

Lord Ventry 1V, who inherited the Ventry estate in 1868, decided to demolish Castleconway House and to use it as a site for a new Courthouse. Almost 80% of the structure was destroyed when Ventry opted for a greenfield site on Market Street.

A section of the 1690’s building can be viewed in Kingston’s Beer Garden.