Street markets are public facilities that link commercial activities and cultural exchange, which interact with the urban fabric that they are a part of. Their historical and symbolic values ​​make them vulnerable to transformations that rethink the urban structure, as happens in the immediate surroundings of the “9 de Octubre” and “10 de Agosto” street markets, located in the historic hub of the city of Cuenca, Ecuador, where processes of gentrification, touristification, and commercial gentrification have taken place. In this context, the proposal here is to analyze the urban and social transformations of the last 50 years, using a mixed methodology with an exploratory approach, through observation, surveys, and interviews. In both case studies, the results showed that with the operation of these street markets, commercial activity increased in the respective areas which, together with other associated issues (insecurity, unhealthy conditions, informal trade), are the main triggers for the incremental displacement of the population.