Road condition affects the operations and costs of vehicles that use the infrastructure. Various models of vehicle operating cost provide an indication of the effects of road roughness on fuel consumption, additional damage to a vehicle, and tire wear. These models do not include the effect of road conditions on the condition of and potential damage to transported freight. Such potential damages are mitigated through the use of improved vehicle technologies or packaging. In agricultural transportation, packaging often is not a solution because the use of older vehicle technology on mostly rural roads with lower levels of riding quality is a main contributor to the problem. This paper evaluates quantified effects of the riding quality on low-volume roads on the level of damage to tomatoes in California. The paper is partly based on a study that focused on vehicle–pavement interaction and its effects on the broader California economy. Vehicle responses to road conditions were measured during operations on a range of rural routes. Laboratory experiments were developed to replicate the dominant vibrations of the trucks and to measure the stresses that tomatoes typically undergo at these vibration levels. The damage and failure levels for the tomatoes during transportation were determined, and these damage levels were used to calculate typical costs to agricultural suppliers that are due to road conditions. The problem thus could be quantified and input data provided for a cost–benefit evaluation of the potential maintenance and improvement of various routes used to transport tomatoes.