The railway sector plays a crucial role in sustainable transportation by reducing greenhouse gas emissions while supporting an increasing volume of freight and passenger transport. Rail pads, essential components in railway infrastructure, mitigate vibrations and distribute loads; however, their long-term performance is influenced by environmental and mechanical degradation, affecting track durability and maintenance costs. Despite their significance, the degradation mechanisms impacting the dynamic stiffness of EPDM (Ethylene Propylene Diene Monomer) and EVA (Ethylene Vinyl Acetate) rail pads remain insufficiently characterized. This study examines the effects of mechanical and chemical aging on the stiffness of these materials through 864 dynamic stiffness tests, analyzing three types of rail pads under mechanical cycling (up to 2,000,000 cycles), UV (ultraviolet light) exposure (100–500 h), and hydrocarbon exposure (100–500 h). Mechanical aging increases stiffness across all pads, with Pad C (EVA) exhibiting the most pronounced increase (27%). The effects of UV exposure vary by material, leading to a stiffness reduction of up to 11.5% in Pad B (EPDM), whereas Pad C (EVA) experiences a 9.5% increase under prolonged exposure. Hydrocarbon exposure also presents material-dependent behavior, with Pad A (EPDM) experiencing an 11.5% stiffness reduction at low exposure but partial recovery at higher exposure, while Pad C (EVA) shows a 5% increase in stiffness under prolonged exposure. These findings offer valuable insights into the aging mechanisms of rail pads and underscore the importance of considering degradation effects in track maintenance strategies.