Upton Train Ambush The Upton Train Ambush took place on 15 February 1921 , during the Irish War of Independence . The Irish Republican Army ( IRA ) mounted an attack on a train carrying British soldiers at Upton , County Cork . The action was a disaster for the IRA ; three of its volunteers were killed and two wounded . Six British soldiers were wounded , three seriously . Six civilian passengers were killed and ten wounded in the crossfire . Background . According to a study of the region , Cork was " by far the most violent county in Ireland " during the War of Independence and had several active guerrilla brigades . Of these , the Third ( west Cork ) was one of the most effective and it was a unit from this Brigade that carried out the Upton ambush . Up until the end of 1920 , the British had been unable to move troops by train , due to a nationwide boycott by railway workers of trains carrying the British military . However , this strike was lifted in December 1920 . While this helped the British military ' s mobility , it also gave the IRA a new target : trains carrying soldiers . A week before the Upton ambush , the local IRA had made a successful attack on a train travelling from Killarney to Millstreet near Drishanbeg , killing one sergeant and wounding five more soldiers . Ambush . Five days after the Drishanbeg ambush , plans were made for an attack at Upton and Innishannon railway station on a train travelling between Cork city and Bandon . The ambushers , led by Charlie Hurley , were 13 strong but had only 7 rifles , the remainder being equipped only with revolver s or semi - automatic pistol s . They took up position at the station ten minutes before the train pulled in , imprisoning the station master , clearing the station and taking cover behind sacks of grain and flour taken from a store . The train was carrying around 50 British soldiers of the Essex Regiment , who were mingled with civilian passengers throughout the train ' s carriages . The IRA party was therefore quite heavily outnumbered and out - gunned . However they were not warned of this , as two IRA scouts , who were supposed to have been on the train and signalled to them of British numbers , never turned up . They also wrongly believed that the British troops were all in the central carriage . As a result , when the IRA opened fire on the train , there were heavy civilian casualties . The " New York Times " reported that " a shower of bullets was rained on the train , practically every compartment being swept " . The firefight lasted for only ten minutes , but in that time six civilian passengers were killed and ten wounded in the firing between the British and IRA . Six British soldiers were also injured , three of them seriously . Two IRA volunteers were killed outright , another was fatally wounded and two more were badly wounded but survived . Charlie Hurley , who had led the ambush , was among the wounded , being struck in the face by a bullet . IRA leader Tom Barry later wrote , " Through some miracle , the nine unwounded and two wounded got away across country , in small parties , with the British following close behind " . Three civilian passengers , one unwounded and two wounded were detained by the British on suspicion of belonging to the ambush party . Aftermath . The Upton ambush was part of what Tom Barry described as " twelve dark days " for the 3rd Cork Brigade of the IRA . Between 4 February and 16 February , eleven members of the Brigade were killed . One was shot dead by British troops when they raided a safehouse on the 4th , another died in an accidental shooting on the 7th , two more ( the Coffey brothers ) were assassinated in their beds on the 14th by Black and Tans or Auxiliaries , three died at Upton on the 15th and four were killed on the 16th when they were arrested by the Essex Regiment in Kilbrittain while digging a trench and shot dead . Of the eleven dead , only those at Upton were killed in combat . The Upton attack also highlighted the dangers , and particularly the risk to civilians , of attacking trains carrying troops . Only a month later at the Headford Ambush in neighbouring County Kerry , an IRA column successfully attacked a train - load of troops , but again , there were civilian casualties alongside the IRA and British Army losses . One of the three men captured by the British at Upton is reported to have given information leading to the Third Cork Brigade ' s main column of over 100 fighters almost being encircled at the Crossbarry Ambush . Hurley himself was killed in this action . The Upton ambush was later made famous in a popular 1960s Irish ballad titled " The Lonely Woods of Upton " .