Demographic, economic, environmental, and political changes shape many rural areas and their communities across Europe. As a result, some fundamental aspects of these communities, including traditions, culture, social fabric, and their very raison d’être, are being tested and threatened by what seem to be irreversible events. Ultraperipheral European regions, including the `Canary Islands, are not an exception; in fact, because of their physical isolation from the mainland and other barriers, these regions may be more susceptible to changes. While these dimensions are very important and need to be addressed, to date very few studies have attempted to do so with regard to European ultraperipheral areas. Using face-to-face interviews among operators of Canary Island wineries, food confectioners, and handcraft artisans, this study seeks to understand how small rural businesses involved in traditional industries in this region cope with contemporary changes. The findings indicate that while generally participants vie to continue their involvement with traditional industries that have characterized the archipelago for centuries, lack of succession and marginal financial viability instill a strong sense of uncertainty about their future. These findings may have several implications for policy makers and local authorities, particularly in the design of strategies to assist small businesses located in ultraperipheral regions.