A trapped ion transported along a periodic potential is studied as a paradigmatic nanocontact frictional interface. The combination of the periodic corrugation potential and a harmonic trapping potential creates a one-dimensional energy landscape with multiple local minima, corresponding to multistable stick-slip friction. We measure the probabilities of slipping to the various minima for various corrugations and transport velocities. The observed probabilities show that the multislip regime can be reached dynamically at smaller corrugations than would be possible statically, and can be described by an equilibrium Boltzmann model. While a clear microscopic signature of multislip behavior is observed for the ion motion, the frictional force and dissipation are only weakly affected by the transition to multistable potentials.