From a historic perspective, the period of Roman rule and the following Middle Ages are polar opposites. For most, the city of Rome and the Western Roman Empire represent a time of advancement for the Mediterranean world while the Middle Ages are viewed as a regression of sorts for Europe. The reasons explaining the underlying cause of this transition from the Western Roman Empire to the Middle Ages are numerous but this paper will specifically focus on the practices started by the Romans themselves and how they contributed to the rise of the Early Middle Ages on the Italian Peninsula. More specifically, economic turmoil and urbanization following the 3rd century crisis in the city of Rome laid the groundwork for social, legislative, and political changes that thread the path to the fundamental characteristics of the Middle Ages. Changing views of the city and the countryside, the construction of latifundia and villas, and the passing of legislation that restricted the rights of laborers, in addition to other transformations in late Rome, all contributed to the decentralized governance, rural life, and serfdom that are characteristic of the Middle Ages. Ultimately, the goal of this paper is to illustrate that despite the major differences that exist between the Roman period and the Middle Ages, the practices of the late Western Roman Empire were often directly carried over into the Middle Ages and, as a result, for one to truly understand the origins of the Middle Ages, it is essential to comprehend the traditions started by the late Romans.