Battle of Vinegar Hill The Battle of Vinegar Hill , Irish Chnoc Fíodh na gCaor was an engagement during the Irish Rebellion of 1798 on 21 June 1798 when over 15 , 000 British soldiers launched an attack on Vinegar Hill outside Enniscorthy , County Wexford , the largest camp and headquarters of the Wexford United Irish rebels . It marked a turning point in the rebellion , as it was the last attempt by the rebels to hold and defend ground against the British military . The battle was actually fought in two locations : on Vinegar Hill itself and in the streets of nearby Enniscorthy . Preparations . By 18 June , the British had surrounded county Wexford with an estimated 20 , 000 troops and were ready to pour into Wexford to crush the insurgency . The rebel leadership issued a call to all its fighters to gather at Vinegar Hill to meet the army in one great , decisive battle . The number assembled was estimated at 20 , 000 , but the majority lacked firearms and had to rely on pikes as their main weapon . The camp also included many thousands of women and children who were staying there for protection against the rampaging military . The British plan , as formulated by Gerard Lake , envisaged the complete annihilation of the rebels by encircling the hill and seizing the only escape route to the west , the bridge over the Slaney . Lake divided his force into four columns to accomplish this ; three columns , under Generals Dundas , Duff and Needham were to assault Vinegar Hill , while the fourth column , under General Johnson , was to storm Enniscorthy and its bridge . Bombardment of Vinegar Hill . The battle began shortly before dawn with an artillery bombardment of Irish positions on the hill . Advance units quickly moved against rebel outposts under cover of the bombardment and moved artillery closer as forward positions were secured . The tightening ring forced the rebels into an ever - shrinking area and increased exposure to the constant bombardment , including new experimental delayed - fuse shells resulting in hundreds of dead and injured . At least two mass charges were launched by the rebels which failed to break the lines of the military and the situation on Vinegar Hill soon became desperate for the rebels . Attack on Enniscorthy . Meanwhile a detachment of light infantry under the command of General Johnson attacked the town of Enniscorthy but met with fierce resistance . Buildings in the town had been fortified , and the initial attack was driven back , with the loss of munitions and men . A second attack commenced with reinforcements including cavalry , which retook the lost cannon and ammunition while also incurring considerable casualties . The Irish rebels were slowly driven out of the town but managed to hold the Slaney bridge and prevent the British from crossing . Rout and atrocities . When British troops crested the eastern summit of Vinegar Hill , the rebels began to slowly withdraw through a gap in the British lines later known as " Needham ' s Gap " , so - named because the late arrival of General Needham ' s troops prevented a total encirclement of the hill . Although the bulk of the rebel army escaped , many were left behind and killed in the rout phase of the battle , from both cavalry and infantry attack , but also from the advanced field guns which were switched to grape shot to maximise casualties . In addition to conventional casualties , the military were guilty of instances of gang rape of females amongst the rebel camp and in Enniscorthy , rebel wounded were burned to death when soldiers set fire to a building used as a casualty station . The Irish rebels abandoned much of the supplies they had taken from surrounding areas , and thirteen cannons were captured by the British , a number of which had been taken from the British forces previously . Archibald McLaren , an eyewitness , wrote that the Irish rebel casualties totalled about 1200 men . Aftermath . Meanwhile , the bulk of the rebel force streamed unmolested towards the Three Rocks camp outside Wexford town and , following the decision to abandon the town , split into two separate columns in a new campaign to spread the rebellion beyond Wexford . One immediately set out to the west , the other northwards towards the Wicklow Mountains to link up with General Joseph Holt ' s forces . The defeat was therefore not the immediate crushing blow to the Wexford rebels that it has traditionally been depicted as , but it did alter the course of the fighting as continued resistance now took the form of mobile warfare , raids , and large scale , guerilla - type operations .