Situated on an island in the St. Lawrence River at the historically highest navigable point, Montreal has been a strategic location since before the arrival of Europeans in Canada. A thriving St.Lawrence Iroquoian town called Hochelaga was on the site of present-day Montreal when explorer Jacques Cartier first visited in 1535. A hundred years later, in 1642, the tiny town of Ville-Marie was founded as a Sulpician mission by Paul Chomedey, sieur de Maisonneuve. It soon became a centre of the fur trade. After its capture by the English in 1762, Montreal remained (until the 1970s) the most important city in Canada and was briefly capital of the province in the 1840s.

Prohibition on sales of alcohol in the United States during the 1920s and 1930s made Montreal a mecca for cross-border fun seekers from nearby New England and New York. The city built up a seedy, yet playful, industry in alcohol, burlesque, and other vices. In the 1960s, an urban renewal drive centred around Expo 67. The World's Fair in Montreal brought a subway system and a number of attractive urban parks and is considered to be one of the most successful World Fairs. Over 50 million visitors gathered to Montreal during this memorable summer. The 1976 Olympics left a strikingly idiosyncratic stadium and many other urban improvements.

The opening of the Saint Lawrence Seaway in 1959, though much lauded as an economic boom, spelled the beginning of the end for Montreal's economic dominance in Canada. Once the transition point between western railroads and eastern sea carriers, Montreal watched helplessly as some of this business moved farther west, up the now navigable Seaway, to ports in Ontario and on Lake Superior. The Quebec Sovereignty movement, which began to pick up steam in the 1960s, further chilled the atmosphere for Canada-wide businesses, many of which moved their headquarters to Toronto.

Following an economic depression in the 1980s and 1990s, Montreal became more secure in its place in North America and the world. It remains a centre of culture, arts, computer technology, aerospace, the biotech industry, and media for all of Canada.