The risk posed by spill and subsequent fire during road transportation of flammable liquid is considered in the paper. Attention is paid to a pool fire than can occur in roadside terrain. Circumstances and road situations increasing the likelihood of a spill and fire accident are analysed. The problem under study is an assessment of thermal radiation induced by a roadside pool fire. This study applied a pool fire model known as a trench fire to a roadside situation. The trench fire is considered to be a likely type of a pool fire due to presence of roadside ditches and other oblong low areas along the road. The estimation of the thermal radiation from trench fires is carried out in the deterministic way due to actual lack of systematic uncertainty modelling related to pool fires. Deterministic models developed for estimating the radiation of pool and trench fires are presented and illustrated by a transportation case study. The case study reveals that the thermal radiation emitted by a trench fire can endanger objects positioned in the intermediate vicinity to the road. Further spread of fire into more distant locations is possible only through the domino effect. Incorporation of the thermal radiation models into a transportation risk assessment is discussed in brief. Findings of this study are viewed as knowledge that can be used for refining the estimation of risk posed by transportation of hazardous materials.