Captain Walter Raleigh (later Sir Walter) had an association with Midleton, living for periods in nearby Youghal between 1585 and 1602. His presence came about due to a distribution of land in reward for helping suppress the Second Desmond Rebellion of 1579–1583. As part of this suppression he was ordered to seize Barry's Castle at nearby Cahermore. The Desmond FitzGerald Seneschal, or steward of Imokilly, on being expelled from the castle, took refuge in the Abbey, but was again forced to flee by Raleigh.