The effectiveness of the economic policies implemented by a country/region directly affects its economic growth potential. Cultural Heritage Festivals are a sector of the creative economy that, by promoting culture, may have a significant impact on national/regional sustainable economic development. This study assesses the implementation of the Contingent Valuation Method (CVM) and the estimation of the Willingness To Pay (WTP) demand curve, using data collected for the Kalamata Dance Festival as a case study, in order to evaluate creative economy investments. The results obtained indicate that the CVM is an appropriate method for evaluating festivals and suggest that females, spectators with high incomes and high educational levels, and visitors to Kalamata (non-residents) show an increased Willingness To Pay. These findings can be useful to cultural heritage festival organizers in developing appropriate policy strategies: targeting the social groups with the greatest Willingness To Pay; adjusting the pricing mechanism accordingly; modifying annual memberships/donations/sponsorships, indirect resources, and tax revenues and grants; and optimizing investments and allocating resources. Furthermore, the findings of this study will be particularly useful for Greece in designing relevant cultural sustainable development policies for exploiting the potential of the Cultural Heritage Festival, in synergy with the tourism sector, which already contributes a major share to the country’s GDP.