Battle of Ortona The Battle of Ortona ( December 20 – 28 , 1943 ) was a small , yet extremely fierce , battle fought between a battalion of German " Fallschirmjäger " ( paratroops ) from the German 1st Parachute Division under " Generalleutnant " Richard Heidrich , and assaulting Canadian forces from the 1st Canadian Infantry Division under Major General Chris Vokes . It was the culmination of the fighting on the Adriatic front in Italy during " Bloody December " . The battle , dubbed " Little Stalingrad " for the deadliness of its close - quarters combat , took place in the small Adriatic Sea town of Ortona , with its peacetime population of 10 , 000 . Background . The Eighth Army ' s offensive on the Winter Line defences east of the Apennine mountains had commenced on 23 November with the crossing of the river Sangro . By the end of the month , the main Gustav Line defences had been penetrated and the Allied troops were fighting their way forward to the next river , the Moro , north of the mouth of which lay Ortona . For the Moro crossing in early December the exhausted British 78th Infantry Division on the Allied right flank on the Adriatic coast had been relieved by Canadian 1st Infantry Division . By mid - December , after fierce fighting in the cold and mud , the Division ' s 1st Infantry Brigade had fought its way to within of Ortona and was relieved by 2nd Infantry Brigade for the advance on the town . Ortona was of high strategic importance , as it was one of Italy ' s few usable deep water ports on the east coast , and was needed for docking allied ships and so shorten Eighth Army ' s lines of supply which at the time stretched back to Bari and Taranto . Allied forces were ordered to maintain the offensive , and going through the built up areas in and around Ortona was the only feasible option . Ortona was part of the Winter Line defence system and the Germans had constructed a series of skilfully designed interlocking defensive positions in the town . This — together with the fact that the Germans had been ordered to " fight for every last house and tree " — made the town a formidable obstacle to any attacking force . The battle . The Canadians faced elements of the renowned German 1st Parachute Division . These soldiers were battle - hardened after many years of war , and were ordered by Adolf Hitler to defend Ortona at any cost . The initial Canadian attack on the town was made on December 20 by Canadian 2nd Brigade ' s Loyal Edmonton Regiment with elements of the Seaforth Highlanders of Canada under command . Meanwhile elements of the division ' s 3rd Infantry Brigade launched a northerly attack to the west of the town in attempt to outflank and cut off the town ' s rear communications but made slow progress because of the difficult terrain and the skilful and determined German defence . The Germans also concealed various machine gun s and anti - tank emplacements throughout the town , making movement by armour and infantry increasingly difficult . The house to house fighting was vicious and the Canadians made use of a new tactic : " mouse - holing " . This tactic involved using weapons such as the PIAT ( or even cumbersome anti - tank guns ) to breach the walls of a building , as houses within Ortona shared adjoining walls . The soldiers would then throw in grenades and assault through the mouse holes , clearing the top floors and making their way down , where both adversaries struggled in repeated close - quarters combat . Mouse - holing was also used to pierce through walls into adjoining rooms , sometimes catching enemy troops by surprise . The tactic would be used repeatedly as assaulting through the streets inflicted heavy casualties on both Canadian and German troops . Later , in a particularly deadly incident , German " Fallschirmjäger " engineer Karl Bayerlein demolished an entire house packed with Canadian soldiers ; only one soldier survived . The Canadians retaliated by demolishing another building on top of two German squads , killing them all . After six days of intense combat , 2nd Brigade ' s third battalion , Princess Patricia ' s Canadian Light Infantry , joined the battle together with tanks from 1st Canadian Armoured Brigade ' s Three Rivers Regiment ( " Régiment de Trois - Rivières " ) . On 28 December , after eight days of fighting , the depleted German troops — who lacked reinforcements — finally withdrew from the town . The Canadians suffered 1 , 375 dead in the fighting in and around Ortona , almost a quarter of all Canadians killed during the Italian Campaign .