This dissertation analyzes the influence of colonialism on the current transportation system in Nigeria, its impact on development and the stringent difficulties experienced in the restructuring of the system for efficient development in the Nigerian economic milieu. These have been accomplished by an analysis of the colonial intentions of the foreign influence under whose auspices the transportation system in Nigeria was initiated and constructed. Also, the post-colonial difficulties in the efforts to restructure the system were critically analyzed. A major assumption made in this dissertation has been that colonialism was the main reason the system was structured the way it stands currently, especially since the system reached its greatest development and expansion during colonialism in Nigeria. All evidences in this study point to the fact that unless the system is completely restructured to better address the developmental needs in Nigeria, development will still be far-fetched and thus negate the importance of transportation as a major vehicle to national development.