The Churchill Centre conducts annual conferences around the world, most recently: 2011 South Carolina, 2010 Washington, DC; 2009 San Francisco; 2008 Boston; 2007 Vancouver; 2006 Chicago.

In late September/early October 2005 the Churchill Centre's annual conference, with the organizing team including ICS Canada Board members, was held at the Chateau Frontenac Hotel in Quebec City with speakers/attendees including Churchill's daughter The Lady Soames, (Patron of ICS Canada), Roosevelt's granddaughter, Anna Eleanor Roosevelt, former Canadian Ambassador to Iran, Ken Taylor and Canadian historians Professor Desmond Morton and Professor Jack Granatstein. Some 230 delegates attended the very successful conference.

Future conferences scheduled - 2011 (Fall) London; 2012 Toronto.

ICS Canada holds an annual dinner in Toronto on or about May 10th to commemorate the date in 1940 when Churchill became Prime Minister of Great Britain and the wartime leader of the British, Canadian and Commonwealth forces.

Events also include "Evenings with Sir Winston" with films, talks and silent book and memorabilia auctions all held in an atmosphere of conviviality and good humour.