Correlated random walks provide an elementary model for processes that exhibit directional reinforcement behavior. This paper develops optimal multiple stopping strategies - buy/sell rules - for correlated random walks. The work extends previous results given in Allaart and Monticino (2001) by considering random step sizes and allowing possibly negative reinforcement of the walk's current direction. The optimal strategies fall into two general classes - cases where conservative buy-and-hold type strategies are optimal and cases for which it is optimal to follow aggressive trading strategies of successively buying and selling the commodity depending on whether the price goes up or down. Simulation examples are given based on a stock index fund to illustrate the variation in return possible using the theoretically optimal stop rules compared to simpler buy-and-hold strategies.