Transportation problems in the country Nigeria are very hectic, especially with so many challenges on the highway, such as: obstacles, armed robbery attacks, insurgency and terrorism, which hinder the free flow of traffic of goods and services. This study is designed to address these challenges by using Dynamic Programming on transportation networks using traditional technique, traditional technique with incorporated task of obstacles and traditional technique with incorporated infrastructural advantages. The data used for analysis were from government agencies. The results obtained from these redesigned three networks were superimposed to obtain the final optimal route from the seaport sources: Lagos, Warri, Port Harcourt and Calabar to Maiduguri are 2998km, 2671km, 2636km and 2491km respectively. The result shows superiority of the new critical path to the normal critical path.