The empirical applications of behavioural freight transport models accounting for several dimensions of decision-making process strengthen our understanding of the impacts of various freight-related policies. Several developments have been made in recent years to model the choices of freight transport actors. In line with these developments, the goal of this research is to apply a set of models which gain insight into the behavioural underpinnings that affect decision-making in freight sectors. However, it should be noted that the complex and heterogeneous nature of freight decision making is an imperative impediment to developing a behavioural model that can represent all dimensions of decision making.While this study acknowledges that there are several choice decisions in the freight transportation system, this PhD study focuses on the most important ones including the choices of shipment size, using transshipment points and duration of storage, choosing the mode/vehicle of transport. Accordingly, this research is an effort to apply some empirical tools and approaches including advanced choice models and agent-based simulation in order to yield further gains in understanding of these particular decisions.Within decision making process of freight transport, there are multiple interrelated constructs that can be tackled from various angles. This research attempts to apply advance choice techniques to model a few of these interrelated decisions in freight transport. To achieve this target, contributions are given to several components of two sets of interrelated decisions by (i) modelling the joint decisions of shipment size and vehicle type using a copula-based continuous-discrete choice model; (ii) modelling the joint decisions of using a container terminal and the resulting dwell-time of staging full containers using a copulabased discrete-discrete choice model.Considering the differences in decision-making between for-hire carriers and ancillary shippers, separate different models are estimated while the assumption of pure utility maximization is relaxed via a hybrid utility-regret specification. Results of a case study show that differences exist between shippers' and carriers' preferences, and they prove the Publications during candidature Refereed Journal Papers 1. Nassir, Neema, Hickman, Mark, Malekzadeh, Ali, and Irannezhad, Elnaz