In this paper, we address the free (uncontrolled) dynamics of a snakeboard consisting of two wheel pairs fastened to a platform. The snakeboard is one of the well-known sports vehicles on which the sportsman executes necessary body movements. From the theoretical point of view, this system is a direct generalization of the classical nonholonomic system of the Chaplygin sleigh. We carry out a topological and qualitative analysis of trajectories of this dynamical system. An important feature of the problem is that the common level set of first integrals is a compact two-dimensional surface of genus 5. We specify conditions under which the reaction forces infinitely increase during motion and the so-called phenomenon of nonholonomic jamming is observed. In this case, the nonholonomic model ceases to work and it is necessary to use more complex mechanical models incorporating sliding, elasticity, etc.