Railway infrastructure plays a major role in providing the most cost-effective way to transport freight and passengers. The increase in train speed, traffic growth, heavier axles, and harsh environments make railway assets susceptible to degradation and failure. Railway switches and crossings (S&C) are a key element in any railway network, providing flexible traffic for trains to switch between tracks (through or turnout direction). S&C systems have complex structures, with many components, such as crossing parts, frogs, switchblades, and point machines. Many technologies (e.g., electrical, mechanical, and electronic devices) are used to operate and control S&C. These S&C systems are subject to failures and malfunctions that can cause delays, traffic disruptions, and even deadly accidents. Suitable field-based monitoring techniques to deal with fault detection in railway S&C systems are sought after. Wear is the major cause of S&C system failures. A novel measuring method to monitor excessive wear on the frog, as part of S&C, based on fiber Bragg grating (FBG) optical fiber sensors, is discussed in this paper. The developed solution is based on FBG sensors measuring the strain profile of the frog of S&C to determine wear size. A numerical model of a 3D prototype was developed through the finite element method, to define loading testing conditions, as well as for comparison with experimental tests. The sensors were examined under periodic and controlled loading tests. Results of this pilot study, based on simulation and laboratory tests, have shown a correlation for the static load. It was shown that the results of the experimental and the numerical studies were in good agreement.