Deep Learning methods have been extensively used to analyze video data to extract valuable information by classifying image frames and detecting objects. We describe a unique approach for using video feed from a moving Locomotive to continuously monitor the Railway Track and detect significant assets like Switches on the Track. The technique used here is called Siamese Networks, which uses 2 identical networks to learn the similarity between of 2 images. Here we will use a Siamese network to continuously compare Track images and detect any significant difference in the Track. Switch will be one of those images that will be different and we will find a mapping that clearly distinguishes the Switch from other possible Track anomalies. The same method will then be extended to detect any abnormalities on the Railway Track. Railway Transportation is unique in the sense that is has wheeled vehicles, Trains pulled by Locomotives, running on guided Rails at very high speeds nearing 200 mph. Multiple Tracks on the Rail network are connected to each other using an equipment called Switch or a Turnout. Switch is either operated manually or automatically through command from a Control center and it governs the movement of Trains on different Tracks of the network. Accurate location of these Switches is very important for the railroad and getting a true picture of their state in field is important. Modern trains use high definition video cameras facing the Track that continuously record video from track. Using a Siamese network and comparing to benchmark images, we describe a method to monitor the Track and highlight anomalies.