Siege of Charlemont The Siege of Charlemont took place in July – August 1650 during the Cromwellian conquest of Ireland when the fortress of Charlemont in County Armagh , Ireland was besieged by Charles Coote ' s Parliamentarian army , which was largely composed of soldiers of the New Model Army . The force led by Coote eventually took the fort from its Irish defenders , but not before they suffered heavy losses , with some 5 - 800 Parliamentarian Soldiers being killed during assaults on the formidable stronghold . In terms of the number of soldiers killed in battle , The Siege of Charlemont was the second bloodiest engagement fought by the Parliamentarians in Ireland , only surpassed by the Siege of Clonmel . Background . Charlemont was the first stronghold to be captured in the Irish uprisng of 1641 , seized a force led by Felim O ' Neill within 24 hours of the outbreak of the rebellion . It was one of the most modern fortrifications in Ireland and as such was one of the few strongholds in Northern Ireland to remain in Irish Confederate hands throughout the 1640s . At the end of 1649 , a force of New Model Army soldiers under Robert Venables moved into Ulster and linked up with Charles Coote ' s small army . The combined force conquered eastern Ulster easily , routing the Scottish Royalist Ulster army at Lisnagarvey . The only serious opposition to the Parliamentarian army came from Felim O ' Neill ' s Ulstermen , who launched a night attack on the Parliamentarian camp , though to little effect . At the end of 1649 , the Irish Ulster army had been momentarily paralysed as a result of the death of Owen Roe O ' Neill . In 1650 Heber MacMahon was chosen to lead the Ulster army , and by mid - 1650 the force was once again active , pushing into Ulster and threatening the forces under Coote . MacMahon however was a bishop rather than a military man , and at the battle of Scarrifholis he led the Ulster army to its destruction . The only senior Irish commander to escape Scarriffhollis was Sir Felim O ' Neill . Along with a small number of survivors , he made his way to Charlemont Fort , the last remaining Irish stronghold in Ulster . Realising that the fort would be near impossible to capture without heavy artillery , Venables and Coote brought Siege Cannon and Mortars with their army when they commenced their attack in late July . The Commanders . Charles Coote , who led the mostly English Ulster army , had a savage reputation – during the Parliamentarian offensive in Ulster in late 1649 , he exhibited brutal behaviour , committing atrocities not only against Irish Catholics but also against any Scottish Protestants who resisted his advance . After his victory at Scarrifholis , he executed all the soldiers , regardless of rank , who had surrendered to the lower ranking Parliamentarian officers : Even Henry O ' Neill , the son of Owen Roe , was put to death . This was considered to be a shocking atrocity , even by the low standards of the time . As a Gaelic Irish Catholic , Felim O ' Neill had good enough reason to fear Coote , but O ' Neill had also featured prominently in English Propaganda pamphlets during the 1640s as the authour of a massacre of Protestants . He was thus hated by many Protestant soldiers in Ireland , and the army surrounding him would therefore be particularly vigilant . O ' Neill did however have a few small points to his advantage . Firstly , the fortress at Charlemont was one of the toughest fortresses in Ireland . Secondly , Coote ' s reputation was by now well known , and no Irish Catholic would be mad enough to willingly surrender to him . The defenders of Charlemont were thus well aware that they would have little hope of survival if the Parliamentarians captured the fortress . The fighting would invariably prove to be fierce . The assault . By early August , the Parliamentarians had managed to batter a breach in the fortifications . Coote then ordered his troops to cut approach trenches up to the walls . On 8 August the English launched a major assault . Felim O ' Neill rallied the entire garrison as well the civilian inhabitants to mount a vigorous defence at the breach - even the women had armed themselves as best they could . The defence was in many respects a repeat of the defence of Clonmel in May : Hundreds of English soldiers were killed by the desperate defenders , and the remainder were forced out of the breach and back to their lines . After this huge effort the garrison was however exhausted , bloodied , and had used up almost all of their gunpowder and ammunition . As a result , on 14 August O ' Neill requested terms of surrender . Sir Felim O ' Neill demanded hostages from Coote before he would negotiate the surrender . The terms that O ' Neill obtained were that he and his men would march out with bag and baggage after their wounds had healed , and proceed to a port where Coote would have ship waiting to carry them overseas . These were a remarkably generous set of terms from Coote : He probably had no other option , for by now few would be willing to surrender to Coote unless extraordinary conditions were offered . Aftermath . The fighting at Charlemont was one of the bloodiest conflicts to be fought in Ireland by the Parliamentarians . Although many more soldiers died at Limerick the next year , these deaths were mostly the result of disease . By contrast , almost all the 500 or more soldiers who died at Charlemont were killed in the attempted storm of the fort . Coote bore a great deal of responsibility for the massive casualties he suffered during the siege . Like other Irish Protestant commanders such as Roger Boyle , he had proven himself ruthless on a number of occasions , executing any enemy who fell into his hands . As such , The Ulster Irish defenders were willing to fight to the death . Felim O ' Neill ' s defence of Charlemont , as well as his overall defence of Ulster in 1649 – 50 , was vigorous , a contrast to his often incompetent handling of the early years of the Irish uprising . Although the terms of surrender allowed O ' Neill to leave , he tried to hide in Ulster , and was eventually found and executed . The fall of the stronghold was another blow for Ormonde ' s reputation . In September the Irish bishops excommunicated any Catholic serving Ormonde , and he left Ireland in December . From a Parliamentarian perspective , the fall of Charlemont completed the English conquest of Ulster and left Sir Charles Coote free to advance on Athlone , the passage to the province of Connacht .