1190	Maud de Quency (granddaughter of the famous Strongbow) marries Philip de Prendergast (son of Anglo-Norman Knight Maurice de Prendergast) and they reside at Enniscorthy Castle from 1190 to his death in 1229. From then until the 1370’s, their descendants, and other Anglo-Norman families rule the Duffry and reside in Enniscorthy Castle
1375	The fief (a defined area of land or territory) of the Duffry  and Enniscorthy Castle are forcefully retaken by Art MacMurrough Kavanagh who regains his ancestral lands. This marks a time of Gaelic Irish revival. The MacMurrough Kavanagh dynasty rule until they eventually surrender the Castle and lands to Lord Leonard Grey in 1536. At this time Enniscorthy Castle is reported be in a ruined condition.
1569	The Butlers of Kilkenny and the Earl of Kildare lead a raid on Enniscorthy town on a fair day, killing numerous civilians and burning the castle.
1581	The poet Edmund Spenser leases the Castle but never lives in it. Historians speculate that this was because Spenser feared the MacMurrough Kavanagh’s.
1585	Henry Wallop receives ownership of the Duffry by Royal Appointment. He exploits the dense forests (the Duffry, An Dubh Tír in Irish, meaning “The Black Country”) surrounding Enniscorthy which brings considerable wealth to the town, and funds the rebuilding of Enniscorthy Castle which we see standing today. Enniscorthy begins to rapidly develop as a plantation town.
1649	Oliver Cromwell arrives in Co. Wexford. Enniscorthy Castle is beseiged by his forces; its defenders surrender, leaving it intact. In December of the same year the Castle once again fell to the Irish (under Captain Daniel Farrell), but two months later Colonel Cooke, the Governor of Wexford, reoccupied the castle.
1798	The Castle is used as a prison during the rebellion. The nearby National 1798 Rebellion Centre tells this epic story, and is well worth a visit.
1863	The Earl of Portsmouth uses the ground floor of the Castle as an estate office. The second floor was used as a registration office for the diocese of Ferns while the upper floor was used as a printing office by John Pilkington who founded the “Enniscorthy News”.
1867	The Castle is used as billet accommodation for extra police who were drafted into the area during the Fenian Rising.
1898	The Castle is leased by Patrick J. Roche from the Earl of Portsmouth. P.J. Roche restores and extends the Castle making it into a residence for his son Henry J. Roche.
1916	Roche family forced to vacate their home as Enniscorthy Castle is occupied by members of the Irish Volunteers during the Easter Rising. The Volunteers hold the town for almost a week before surrendering on May 1st.
1922	Roche family vacated the Castle for a period of time after it was commandeered by the Free State Army during the Irish Civil War.
1951	Roche family leaves.
1962	Castle opens as Wexford County Museum.
2006	Closure of the Castle for major renovations.
2011	Reopening of Enniscorthy Castle in May as “A View from the Keep”. Change of focus from a county museum to depicting the story of Enniscorthy town through the eyes of the castle, and how both have developed over the centuries.