The persistence of decline in peripheral regions has led to a renewed interest in the mechanisms that can allow their firms and economies to restructure and to change their growth path. One of the most prolific literatures in recent years has been the one examining path development in its multiple trajectories. What these concepts often lack is a framework that allows them to offer a more explicit analysis of how path development at the industry level generates development in terms of employment and economic growth. In particular, one aspect which it has not adequately addressed is the relationship between endogenous (to the region) and exogenous (national or international) processes. This paper will contribute to this literature by focusing in particular on the challenges to regions specialised in mature industries through two empirical analysis. The first is a descriptive analysis of secondary statistic for four mature sectors in Portugal and the regions where they are located. These data are then complemented with an in-depth analysis of three case studies of wine regions. Our results demonstrate the danger of assuming that because a sector has been capable of catching up technologically it would automatically translate into regional development on an aggregate level.