In the context of smart cities, direct current overhead contact lines, usually adopted to power urban transportation systems such as trolleybuses, tramways, metros, and railways, can serve as a backbone to connect different modern emerging technologies. Among these, in-motion charging (IMC) trolleybuses with on-board batteries are expected to be very impactful on the DC network’s power flow and may require specific voltage and current control. These factors motivate the development of a simulation tool able to emulate these devices’ absorption and their effect on the supply infrastructure. The main innovative value of the work is to improve a simulation model of a trolleybus grid through a data-driven approach by using measurements of voltage and current output from a traction substation. The measurements are essential for understanding the behavior of vehicle weight variation throughout the day. Thanks to this information, a characterization of the current draw by conventional trolleybuses and IMC trolleybuses is then provided for each trolleybus route in a specific power section of the Bologna trolleybus system. By integrating the variation in vehicle weight within the model, a simulation of a possible daily operation of a trolleybus feeding section has been performed, obtaining a 7% error between the daily energy calculated from the simulation and that obtained through measurements. This analysis demonstrates the feasibility of the adopted simulation tool, which can also be used to evaluate additional hypothetical trolleybus operation scenarios. One of these possible scenarios considers IMC vehicles, and it is also evaluated in this paper.