28 May 1798: Enniscorthy was captured from the British on this day. The Wexford insurgents, amounting to several thousand people, had that morning marched northwards to Camolin. By midday they were at Ferns and by the early afternoon they had reached the outskirts of Enniscorthy. They now numbered about 7,000 people. The Crown Forces that opposed them there were supplied with small arms but had no artillery and numbered only about 300 soldiers. The Wexfordmen were without artillery too and mostly carried pikes and homemade weapons. Nevertheless they stormed the town and drove the British southwards toward Wexford Town. Enniscorthy was left more or less a blackened ruin. As a result the United Irishmen made Vinegar Hill, just to east of the town their headquarters.

Members of the Crown Forces under Sir James Duff slaughtered 350 insurgents at the Curragh, Co Kildare. They had gathered there to surrender their weapons on agreed terms. Once they had laid down their arms the massacre began. The chief culprits in this were Roden's Light Dragoons, including the Monasterevan cavalry along with other militia units. Many others were wounded and others either fled on realising what was happening or feigned death till the troops departed.

At Enniscorthy the released captives Edward Fitzgerald and John Henry Colclough, arrived from Wexford Town with a message from the British Commander there. They gave a message that they should disperse and return to their homes or face retribution. Fitzgerald and Colclough had both been arrested two days before as suspected members of the United Irishmen. The British seemed to have assumed they might have enough influence with the Insurgents to persuade them to call off their campaign. In a dramatic moment though, the crowds in the town persuaded both men to join them and the Leadership decided to lead the thousands of armed men they now had under their control, southwards to attack Wexford Town.