(1) Background: The equality of life chances in Germany is often assessed along the lines of a west/east and urban/rural differentiation in which the latter usually perform worse. One currently popular proposal for addressing these inequalities is to strengthen cultural and arts education. The question arises to what extent regional characteristics genuinely influence participation opportunities and to what extent individual resources still play a decisive role. (2) Methods: Using descriptive analyses and multilevel logistic regression modelling, we investigate the distribution of and participation in non-formal cultural education amongst German youth. (3) Results: We find that differences are more complex than a simple west/east or urban/rural divides. Rather, cultural activities must be considered in terms of their character in order to assess the mechanisms at play. There seem to be differences in the dependency on district funding between very peripheral and very central districts that frame the cultural infrastructure. (4) Conclusions: Regional discrepancies are not uniformly distributed across different fields of education or infrastructure. Simplifying statements that classify peripheral regions the general losers can be refuted here. Simultaneously, more comprehensive data could yield significantly more results than we are currently able to produce.