The present competitive world of transport particularly the rail industry is driven by automation and centralization. New ways are being devised each day by the operators and managers to improve efficiency, operational safety, and risk control. Big Data and its multiple applications play a significant role in developing ways of analyzing and evaluating the rail data gathered and using it to enhance the transport industry. Wayside train Monitoring System is a field that is slowly gaining popularity through the different methods it provides to handle the big Data of the transport industry. It can measure the operational performance of rolling stock and infrastructure assets as well as the direct surroundings. The chapter addresses the problem of overall safety and optimum cost of railways transportation. Consequently, the chapter aims to resolve the following issues: How can the rail industry leverage the enormous amount of data available? How can industry players benefit from the data and use it to understand the real needs of travelers?