High-temperature Superconducting (HTS) maglev trains are vulnerable to the effects of crosswinds when operating at high speeds in open-air conditions, potentially compromising riding comfort and safety. This study established a vehicle dynamic model based on the nonlinear maglev-track relationship and added aerodynamic loads under crosswinds to the train’s simplified load center to address this issue. Using the maximum vibration acceleration limit and the Sperling index, we evaluated the riding comfort of the HTS maglev train under different conditions. Further, the vibration acceleration power spectral density was analyzed to reveal the impact of increasing the train’s operating speed and crosswind speed. The results indicated that the lateral and vertical Sperling index achieved an “excellent” rating, even at crosswind speeds of up to 20.7 m/s when the train was traveling at speeds of up to 600 km/h. However, it was noted that particular attention should be given to the riding comfort in the head car when the speed reaches 600 km/h. Moreover, the influence of the increase in train speed on the vibration frequency domain distribution of the three car bodies and the train’s riding comfort is greater than that of the increase in the crosswind speed. These findings may provide a valuable reference for the future engineering application of the HTS maglev train.