This paper explores on- and off-street parking for unloading operations in an urban retail street. A discrete-event simulation is developed introducing a comprehensive model to investigate urban freight unloading operations and to assess managerial and policy implications. To consider both the environmental and economic impact, the problem settings is investigated considering the impacts on lead times, delays and emissions. Therefore, various emission factors based on vehicle load, waiting times and driving mode are integrated. First results indicate the influence of improved unloading operations on lead time and emissions.