Transition zones in railway tracks are locations with considerable changes in the vertical stiffness of the rail support. Typically they are located near engineering structures, such as bridges, culverts, tunnels and level crossings. In such locations, the differential settlement always exists and continually grows without proper maintenance. Due to the effect of the differential settlement and bending stiffness of the rails, hanging sleepers may exist, which are invisible under ordinary circumstances, but generate high displacements and impact during train passages. Therefore, a method to detect the differential settlement (Or hanging sleepers) of track transition zones is presented, which is combined with numerical simulations and field measurements. The numerical model of the track transition zone developed here uses contact elements for modelling the connection between the sleepers and the ballast, bilinear springs for fastening system and Hertzian spring for wheel-rail interaction. The model is capable for simulating the dynamic behaviour of the transition zones with differential settlement or hanging sleepers. Using the model, the dynamic responses such as the vertical displacement of rail, the dynamic wheel load, the axial stress in rail and the vertical stress of ballast has been be obtained and analysed. The field measurements were performed as well. Using Video Gauge System (VGS) the vertical displacements of rail in the vicinity of a track transition zone were measured. The differential settlement of the measured transition zone was analysed by comparing the measurement and numerical results. Finally, based on the obtained findings and the simulation results some track design improvements and suggestions for maintenance actions are given.