In this paper, we present an improved wheelset motion model with two degrees of freedom and study the dynamic behaviors of the system including the symmetry, the existence and uniqueness of the solution, continuous dependence on initial conditions, and Hopf bifurcation. The dynamic characteristics of the wheelset motion system under a nonholonomic constraint are investigated. These results generalize and improve some known results about the wheelset motion system. Meanwhile, based on multiple equilibrium analysis, calculation of Lyapunov exponents and Poincaré section, the chaotic behaviors of the wheelset system are discussed, which indicates that there are more complex dynamic behaviors in the railway wheelset system with higher order terms of Taylor series of trigonometric functions. This paper has also realized the chaos control and bifurcation control for the wheelset motion system by adaptive feedback control method and linear feedback control. The results show that the chaotic wheelset system and bifurcation wheelset system are all well controlled, whether by controlling the yaw angle and the lateral displacement or only by controlling the yaw angle. Numerical simulations are carried out to further verify theoretical analyses.