The postal and philatelic history of Canada concerns postage of the territories which have formed Canada. Before Canadian Confederation, the colonies of British Columbia and Vancouver Island, Prince Edward Island, Nova Scotia, New Brunswick and Newfoundland issued stamps in their own names. The postal history falls into four major periods: French control (1604–1763), British control (1763–1841), colonial government control (1841–1867), and Canada, since 1867.

At St. John's, Newfoundland on 3 August 1527 the first known letter was sent from North America. While in St. John's, John Rut had written a letter to King Henry VIII on his findings and his planned voyage. The letter in part reads as follows: "Pleasing your Honourable Grace to heare of your servant John Rut with all his company here in good health thanks be to God." The conclusion of the letter reads:

...the third day of August we entered into a good harbour called St. John and there we found Eleuen Saile of Normans and one Brittaine and two Portugal barks all a fishing and so we are ready to depart towards Cap de Bras that is 25 leagues as shortly as we have fished and so along the Coast until we may meete with our fellowe and so with all diligence that lyes in me toward parts to that Ilands that we are command at our departing and thus Jesu save and keepe you Honourable Grace and all your Honourable Reuer. In the Haven of St. John the third day of August written in hast 1527, by your servant John Rut to his uttermost of his power.

The earliest reference to a postal service is of couriers in 1705, namely the "first courier" Pedro da Silva, carrying the Governor's dispatches by boat, along with (for a fee) private letters. A regular postal system was proposed in 1721, but would have been too expensive at the time, and was not created until 1734, when a road existed between Montreal and Quebec. Post houses were established at intervals of nine miles (14 km) or so, along with ferries across the rivers. Fees were ten sols between the two major cities, and five sols to Trois-Rivières, Quebec.

The British captured Montreal in 1760, and shortly thereafter established a military postal system that handled letters between Quebec and Montreal, and from Montreal to Albany, New York.

The peace treaty of 1763 inaugurated the development of a civilian post. The Postmasters General of the American colonies, Benjamin Franklin and William Foxcroft surveyed a route between New York and Quebec, and contracted Quebec-Montreal mail to a Hugh Finlay, who provided a weekly service at 8d per letter. Mail to New York took two weeks and cost about a shilling. The service was quite successful, the Quebec-Montreal route increasing to twice a week, and eventually branching out to include Skenesborough.

The American Revolutionary War disrupted mail to New York, and also showed the weakness in not having an all-British route to Halifax, Nova Scotia. In 1787 a complicated route was set up through Riviere du Loup, Fredericton, Digby, and Annapolis. Upper Canada had its own semi-monthly route through Kingston, Niagara, Detroit, and as far as Michilimackinac on Lake Huron.

Finlay was succeeded in 1800 by George Heriot, then in 1816 Daniel Sutherland took over as Postmaster General. By this time dozens of post offices were being opened. 1816 was also when the postal services of Prince Edward Island and Nova Scotia were separated, and not rejoined until 1868.