The paper approaches territorial cohesion in SEE from the perspective of social equity with regard to the opportunity to choose to live in one’s native place without compromising the quality of life. It is interested in border areas - both physical and virtual; in real life situations as meeting points of theories and policies influencing human lives; and in the emerging challenges there that often make us question once and again our concepts and actions as experts. Based on the Bulgarian case-study analysis, the authors discuss the effectiveness and current challenges of real-life implementation of EU and national policies aimed at sustainable development of peripheral regions. The rural peripheral municipality of Ivaylovgrad is an indicative case study for the ongoing processes in the peripheral regions of Bulgaria and the efforts to overcome a continuing loss of working places, services, markets and further isolation from the rest of the country since the early 1990s. The paper presents a critical view of initiatives and projects undertaken by interest and local groups in the period 2006-2010. Possible innovative approaches for regional revival are considered and conclusions are drawn about the importance of creating development strategies sensitive to the existing and emerging socio-cultural patterns.