High-temperature superconducting (HTS) pinning maglev has achieved rapid development in recent decades. The levitation system of the HTS pinning maglev is mainly composed of Dewar with built-in HTS bulks and permanent magnet guideway (PMG). For a maglev transportation system, damping is important for vibration attenuation, and the inherent damping characteristics of the HTS pinning maglev system have not been evaluated clearly. In this paper, the damping characteristics of the HTS pinning maglev system are analyzed through experiments and simulations. Experiments are conducted to measure the dynamic responses of the system under free and forced vibrations. The logarithmic envelope method is used to evaluate the system damping under free vibration. The cross-correlation function is utilized to obtain the phase difference between the system vibration signal and excitation signal, and then calculate the system damping under forced vibration conditions. In addition, a two-dimensional finite element model including HTS bulks, PMG, and Dewar conductive shells is established to evaluate the damping force generated by each component during system vibrations. The additional eddy current damping of the conductive Dewar shell is considered and analyzed. Finally, from the perspective of system damping and thermal stability of HTS bulks, suggestions for selecting Dewar shell materials are proposed.