Proper measurements are extremely significant for the forest owner, the harvesting company, the hauler, the final buyer, and the wood processing company. The accuracy of round wood volume determination is of fundamental importance in planning and accounting for individual processes related to the wood trade. It is the basis for determining the maximum quantity in single load of wood that allows for using the permissible total gross vehicle weight. The determination of wood load in cubic meters does not allow unequivocally determining its weight, which often leads to overloading of vehicles. This paper presents a comparison of the photo-optical method for determining the volume of wood to be transported with the real measurement and determination of the weight of a load and the total gross vehicle weight (GVW) with the simultaneous application of conversion factors determining the weight of the load from the volume of wood. The measurement included 23 broadleaf round wood piles (193.73 m3) and 14 coniferous round wood piles (149.23 m3). The measurement error for broadleaf wood piles ranges from −47.67% to 63.16%, and from −43.31% to 24.72% for coniferous wood piles. Determination of the volume of a broadleaf wood pile using the iFOVEA method had an average error of 1.34%, while the Timbeter method had an average error of −1.83%. In the coniferous wood pile measurement, the error is −12.82% and 2.41%, respectively. Verification of the volume of the large-sized wood indicated on the delivery note (reference value) on the log sorting line (by laser scanning) showed larger volumes by 0.10 m3 to 2.54 m3, giving a percentage error of 0.35% and 8.62%, respectively. As a consequence of the application of such methods for determining the weight of wood loads, the transport truck sets are often significantly overloaded, which has a significant impact on the accelerated degradation of roads and safety in traffic and timber transportation.