Inspired by the utilization of dogs in sled-pulling for transportation, we introduce a cable-trailer system with a quadruped robot. The motion planning of the proposed robot system presents challenges arising from the nonholonomic constraints of the trailer, system underactuation, and hybrid interaction through the cable. To tackle these challenges, we develop a hybrid dynamics model that accounts for the cable's taut/slack status. Since it is computationally intense to directly optimize the trajectory, we first propose a search algorithm to compute a sub-optimal trajectory as the initial solution. Then, a novel collision avoidance constraint based on the geometric shapes of objects is proposed to formulate the trajectory optimization problem for the hybrid system. The proposed trajectory planning method is implemented on a Unitree A1 quadruped robot with a customized cable-trailer and validated through experiments.