In this paper, the authors present a simulation-based scheduling system designed to assist in barge dispatching and boat assignment problems for inland waterways. Specifically, the system assists in the assignment of barge freight to boats. The simulation platform provides the ability to explicitly consider time-based cost trade-offs between barge handling requirements and equipment dwell time. The efficacy of use for the system is demonstrated via case studies utilizing data provided by American Commercial Barge Line, LLC (ACBL) for the Ohio River in North America. The scheduling system described herein is now being implemented as ACBL’s primary dispatching tool for the Ohio River. Results indicate that the solution approach is viable for general use in large-scale dispatching and load assignment problems on major commercial rivers.