The dimensions and weight of machines, structures, and components that need to be transported safely by road are growing constantly. One of the safest and most widely used transport systems on the road today due to their versatility and configuration are modular trailers. These trailers have hydraulic pendulum axles that are that are attached in pairs to the rigid platform above. In turn, these modular trailers are subject to limitations on the load that each axle carries, the tipping angle, and the oil pressure of the suspension system in order to guarantee safe transport by road. Optimizing the configuration of these modular trailers accurately and safely is a complex task. Factors to be considered include the load’s characteristics, the trailer’s mechanical properties, and road route conditions including the road’s slope and camber, precipitation and direction, and force of the wind. This paper presents a theoretical model that can be used for the optimal configuration of hydraulic cylinder suspension of special transport by road using modular trailers. It considers the previously mentioned factors and guarantees the safe stability of road transport. The proposed model was validated experimentally by placing a nacelle wind turbine at different points within a modular trailer. The weight of the wind turbine was 42,500 kg and its dimensions were 5133 × 2650 × 2975 mm. Once the proposed model was validated, an optimization algorithm was employed to find the optimal center of gravity for load, number of trailers, number of axles, oil pressures, and hydraulic configuration. The optimization algorithm was based on the iterative and automatic testing of the proposed model for different positions on the trailer and different hydraulic configurations. The optimization algorithm was tested with a cylindrical tank that weighed 108,500 kg and had dimensions of 19,500 × 3200 × 2500 mm. The results showed that the proposed model and optimization algorithm could safely optimize the configuration of the hydraulic suspension of modular trailers in special road transport, increase the accuracy and reliability of the calculation of the load configuration, save time, simplify the calculation process, and be easily implemented.