This paper will present the development of the Vukovar region from prehistoric times to the present day. The work primarily tries to introduce the geographical position of Vukovar, to better understand the importance of its geographical location in many conquests and influences. It discusses the dynamic settlement in this area and the city development in the Middle Ages. The counties' formation, their disintegration and the re-establishment of VukovarSrijem County are described. From the 10th century, the county institution has marked the internal structure of Croatia. In the earliest times, parishes were organized as centres of power, and later parishes became counties, which to some extent conflicted with the rulers. Based on the relevant literature, we talk about aristocrats and noble families who held high positions in the Vukovar area and managed the county. Given the limited space of this paper, the most significant moments of Vukovar's destiny amid the Homeland War are presented. What preceded the war is also mentioned along with the consequences for the entire Vukovar region. The final part of the work offers the advantages the Vukovar region can provide for economic reconstruction after challenging days of aggression, occupation and integration, including developmental challenges.