Cultural events—religious and countryside festivals, traditional celebrations—produce seasonal and temporary variations in tourist flows, whose impact is particularly significant for locations with low tourist attractivity. The cultural stratification of the Mediterranean territory has led to a high proliferation and diversification of these events in the Mediterranean landscape. Moreover, the distance from major centers has contributed to the preservation of local traditions and gastronomic peculiarities in inner areas, where several events and festivals related to these typical features are reported. On the one hand, this represents an opportunity for rebalancing tourist flows, which tend to be higher in coastal areas, and this is associated with economic advantages; on the other hand, the overabundant presence of visitors compared to the number of residents and the episodic oscillation of tourism flows may produce management diseconomies and may not be fully valorized. This contribution performs an economic and extra-economic analysis of these phenomena in the inner areas of the Sicily Region, where the two characteristic aspects outlined above—the wide presence of local cultural events in small towns and the low supply of tourism facilities—are marked. The analysis will draw from tourism indicators, particularly assessing tourism supply and tourism pressure, and quantify the current and potential economic benefits of occasional cultural and gastronomic tourism. Through a survey of the distribution of cultural events and festivals and an analytic focus on some case studies, this paper provides an insight into their economic and extra-economic impact and possible enhancement actions.