The Siege of Enniskillen took place at Enniskillen in Fermanagh, Ireland, in 1594 and 1595, during the Nine Years' War. In February 1594, the English had captured Enniskillen Castle from the Irish after a waterborne assault and massacred the defenders after they surrendered. From May 1594, an Irish army under Hugh Maguire and Cormac MacBaron O'Neill besieged the English garrison in the castle, and in August they defeated an English relief force. A second relief force was allowed to resupply the garrison, but the castle remained cut off. Eventually, in May 1595, the English garrison surrendered to the Irish and were then executed.
Enniskillen Castle sat on the River Erne and commanded the strategic bottleneck between Upper and Lower Lough Erne. On 25 January 1594, English Captain John Dowdall arrived at Enniskillen by boat with three infantry companies. They dug trenches in which they placed light cannons and musketeers, but the cannons were too small to make much of an impact on the castle walls.. On 30 January, Captain George Bingham arrived with 300 men. They launched a waterborne assault on the castle. While musketeers in boats and artillery on land fired at the castle, a large boat holding 67 men anchored at a vulnerable part of the walls. They made a breach in the wall with pickaxes, forcing the Irish to take shelter in the keep. Dowdall threatened to destroy the castle with gunpowder if the garrison did not surrender. An Irish witness claimed there were 36 fighting men and 40 women and children in the castle, while Dowdall claimed there were 200. After they surrendered, Dowdall had them put to the sword and claimed to have killed 150. Captain Thomas Lee, who was present, described this as a great dishonor to the Queen as the defenders had surrendered "uppon composicion, And your majesties worde being past to the poore beggars that kept it, they were all notwithstandinge dishonourably putt to the sworde in a most miserable state". Dowdall wrote on 2 February to the Lord Deputy that he had captured the castle from the "rebel" Hugh Maguire. An English garrison was left in place. A detailed coloured illustration of the siege was made shortly after.
Second siege
On 17 May 1594, now acting with the covert support of Tyrone, Hugh Maguire and Cormac MacBaron O'Neill laid siege to Enniskillen which was now isolated in hostile country. Their army consisted of 1,400 foot soldiers and 600 horsemen. It quickly grew with support arriving from Hugh Roe O'Donnell. The English commander, James Eccarsall, had only 50 foot soldiers and 24 horsemen to defend the castle, along with some light artillery. Eccarsall launched a sortie by boat but had to retreat under heavy fire. Irish fortifications cut off access by river and the castle was attacked nightly. Many of the garrison fell sick due to food shortages and exhaustion brought on by incessant skirmishing with the Irish. On 7 August, Maguire and his allies defeated an English relief force for Enniskillen at the Battle of the Ford of the Biscuits. A second relief force commanded by the Lord Deputy William Russell was sent by another route. Although it was not attacked by the Irish, none of Russell's scouts or messengers reached the castle nor returned. Russell relieved the beleaguered garrison by 30 August with six months supplies, then withdrew. Following this, there was a truce, but "subterfuge and deception were the hallmarks of this stage of the war".
Third siege
The castle was again attacked by Maguire's troops in January 1595. Forty picked men dressed in chain mail and armed with axes attacked at night. His men overran the outer defences but the garrison held out in the tower. The Irish withdrew but took with them the garrison's three boats, preventing the English from patrolling the Erne and cutting them off. The garrison's plight was not lost on the authorities in Dublin, but the Crown did not have enough troops for a relief force, and Lord Deputy Russell considered withdrawing the garrison. A report to the Lord Deputy suggested that the Irish planned to bring down the walls with gunpowder. In May 1595 the garrison agreed to surrender Enniskillen in exchange for their lives. However, the entire garrison was then massacred. Russell reported that the garrison had surrendered on terms to Cormac MacBaron O'Neill, who later reneged on his word and had the garrison executed. This was inconsistent with the treatment of other English garrisons, such as the Blackwater Fort, who were granted liberal terms to leave their position in February 1595. However, the Enniskillen garrison may have been killed in retaliation for Dowdall's massacre of the Irish defenders of the castle the year before.
