At around two o’clock in the afternoon of September 10, 1944 the Queen Mary carrying Winston Churchill and his entourage arrived at Halifax after a five-day voyage from the Clyde. An hour later Churchill disembarked to board a waiting train bound for Quebec and the OCTAGON conference with President Franklin Roosevelt and the Americans. Malcolm Macdonald, the British High Commissioner to Canada, and Canadian dignitaries welcomed the prime minister while the large crowd of several hundred who had gathered gave him a “tremendous” reception as he came ashore and transferred to the train. Wearing a naval cap and Trinity House jacket with a cane and the ever-present cigar, Churchill waved the “V” salute to the crowd as he boarded his private car. The Canadians responded by singing “Roll Out of the Barrel” and “There’ll Always be an England,” which prompted Churchill and his wife Clementine to step out onto the car’s platform. Churchill requested the crowd sing “It’s a Long Way to Tipperary” and then led them in a rendition of “Pack Up Your Troubles.” Churchill addressed the crowd declaring that, “This is not the first time we have been here in the war, but we have never been here when the skies were brighter.” The prime minister, who had been in bed unwell on the trans-Atlantic voyage, was “deeply moved” and later said that the singing had done much to cheer him up.

The British delegation for the conference included Lord Moran (the prime minister’s physician), Lord Leathers (Minister of War Transport), Lord Cherwell (Paymaster-general), Marshal of the Royal Air Force Charles Portal (Chief of the Air Staff), Admiral of the Fleet Andrew Cunningham (First Sea Lord), Field Marshal Alan Brooke (CIGS), Major-General R.E. Laycock (Chief of Combined Operations), and General Hastings Ismay (Chief of Staff to the Minister of Defence).