The growing necessity to design and digitally representation of historical pavements has led the specialists to use different Building Information Modelling (BIM) tools to control the road design and construction phases. In this chapter, a Heritage BIM (H-BIM) approach was developed to recreate an archaeological road to accomplish the disruption analysis of stone pavements. In detail, within Autodesk Infraworks the conceptual model of the road and the digital terrain model (DTM) was generated; then the road corridor design process was performed within Autodesk Civil 3D using a parametric road section which was created by means of Subassembly composer, a Civil 3D extension. Subsequently, a visual programming application, Dynamo, based on Python language, was adopted to extract and update corridor information. In detail, a workflow was developed to implement a disruption analysis of road stone pavements and the output of the calculation were inserted in the model. As preliminary results, a tool is proposed to support the authorities and experts during the managing process.