Rural areas in Europe have been undergoing structural change for years, resulting in strong functional differentiation and fragmentation into prosperous and structurally weak areas. Rural areas are as diverse as the challenges they face. Not only various megatrends but also social, economic, technological, ecological, and political trends influence and shape the development of rural areas. In order to understand the problems and causes of the current development of rural areas, this paper provides a differentiated trend analysis for rural areas at the European level. A content analysis of more than 70 EU-funded project reports on rural areas and rural development is carried out. The aim is to identify trends and their drivers over the last decade and to summarize opportunities and challenges for successful rural regeneration. These external and overarching trends, particularly in the context of a sustainable transition, renewable energies, the emergence of new technologies and growing awareness of environmental impacts, offer rural areas more opportunities than ever before. The interplay between external incentives (e.g., European Union policies) and endogenous regional development (e.g., local actors) is crucial for the successful exploitation of these opportunities for rural regeneration.