During motion from deep to shallow water, multiple equilibria may emerge, each with identical drag -a phenomenon that can be explained by a localised amplification of the wave drag near the shallow wave speed. The implication of this is the emergence of several previously unstudied bifurcation patterns and hysteresis routes. Here, we address these nonlinear dynamics by considering the quasi-steady motion of a body between deep and shallow water, where the depth is slowly varying. We survey several theoretical models for the drag, compare these against our tow-tank experimental measurements, and then use the validated theory to explore the bifurcation patterns using two parameters: the depth of motion and the forcing. In particular, using a case study of a lake with a sinusoidal depth profile, we illustrate that hysteresis effects can play a significant role on the speed of motion and journey time, presenting interesting implications for naval and racing applications.