Canada's stamp history has been defined in no small part by the country's relationships with its neighbor to the south, the United States, and its parent country, Great Britain. One can divide the history of Canada's stamp production into four eras. Between 1608 and 1763, the French governed the country's postal routes. Few, if any, collectibles exist from this era.

Following the French Canadian war, Great Britain took hold of Canada's postal governance and created a triangular postal region which stretched from Quebec to Montreal to Albany, NY. British control lasted until 1851. Some Canadian stamps from this era do exist, but they're exceedingly rare. Almost every Canada stamp of this era was rigorously tested and poorly preserved, and few proof condition pieces exist today.

During the U.S. Revolutionary War, Canada's postal relationship with both the United States and Great Britain suffered extensive damage. Without American access through Albany, Canadian postal workers had to resort to a labyrinthine mail delivery system. The price of Canadian stamps skyrocketed, and the lack of available postage actually created huge pressures on the nation's already exhausted economy.

In 1816, a man by the name of Daniel Sutherland took the reins of the Canadian postal system and opened scores of offices throughout the country, even in remote places like Prince Edward Island. Upper Canada's postal system was, by and large, autonomous from the main postal systems of Quebec and Montreal. Specials stamps for these Upper Canadians provinces were pressed.