The aim of this paper is to discuss how medium-sized cities can network effectively in order to attract population and activities in a globalizing society where urban regions keep growing often within the pattern of urban sprawl and where national governments keep sector planning still dominant over comprehensive regional planning. The case study introduces three towns (Vila Real/Régua/Lamego) located a hundred km east of the Metropolitan Area of Oporto and along the main national interior road, a connecting north-south axis. This hilly area is not sustaining its population, despite a regional plan approved in 1991 that for the first time assumed the need to develop these three towns as a major anchor in the interior northern Portugal. More than ten years past, two of these towns keep losing population to the coastal strip while the remaining other (Vila Real) has started to attract population. With significant different economic basis, split by physical constraints and historical sub-regional divides what appeared to planners to be the ideal solution and was appraised by politicians is taking a long time to develop. Infrastructure development has been lagging behind due to the high costs of building a motor way in a topographically constrained territory and in costly land as it is Port wine production area, part of it classified recently as World Heritage Area. This has probably been a major factor in hindering the interconnectivity of these three towns. In fact, what could be a 15 minutes safe trip is still taking almost one hour in ice-slippery winding roads. But other factors can be reported, namely initial lack of access to a national program with European Community funds targeting medium-sized towns for the two depressed towns. These factors among others will be put forward and discussed for further insight of the problems faced by medium-sized cities and especially their time lengthy process of reversing trends of losing population to urban regions
