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At the beginning of the 1920s, the city of Montreal found itself in a rather unique situation. At the time, the United States and every Canadian province with the exception of Quebec had adopted prohibition of alcohol. Yet even in Quebec, about half of the population of the province was under local prohibitions (voted at the municipal level) since the beginning of the 20th century, prohibitions which persisted for the most part throughout the period under study. During this era of prohibition of alcohol in North America, Montreal was the largest city, and one of the only on the continent, not under prohibition. It was also the city living under the most liberal alcohol laws on both sides of 49th parallel thanks to the creation of the Quebec Liquor Commission (QLC), the first system of government control of alcohol in North America. Thus, Montreal became a rare oasis in a continent left parched by prohibition and the largest guinea pig of the government control model. This thesis examines the impacts of this conjuncture on the development of the city, specifically of its tourism industry, its nightlife, and its reputation. The thesis begins with a contextualization of prohibition in the United States, in Canada and in Quebec in order to reveal the uniqueness of Montréal during this period. Next, the rapid expansion of « liquor tourism » as well as the city’s nightlife, both legal and illicit, are explored. Lastly, this thesis explores the impact that this conjuncture had on the construction of the city’s reputation throughout the writings of anti- and pro-prohibitionists, who propagated both idealised and demonised views of the city, as well as the documents associated with the tourism boom, such as songs, tourist guides and travel writing, which presented a more romanticized vision of the city as a festive refuge from prohibition. Despite their differences, these three visions all associated Montreal with liberty, whether it is one that is well managed by the government, dangerous and out of control, or emancipating. Thus, through the era of prohibition and the phenomenon of liquor tourism, Montreal came to be known as an “open” city, in both a positive and a negative sense.