Technological advances in the telecommunications industry have brought significant advantages in the management and performance of communication networks. The railway industry is among the ones that have benefited the most. These interconnected systems, however, have a wide area exposed to cyberattacks. This survey examines the cybersecurity aspects of railway systems by considering the standards, guidelines, frameworks, and technologies used in the industry to assess and mitigate cybersecurity risks, particularly regarding the relationship between safety and security. To do so, we dedicate specific attention to signaling, which fundamental reliance on computer and communication technologies allows us to explore better the multifaceted nature of the security of modern hyperconnected railway systems. With this in mind, we then move on to analyzing the approaches and tools that practitioners can use to facilitate the cyber security process. In detail, we present a view on cyber ranges as an enabling technology to model and emulate computer networks and attack-defense scenarios, study vulnerabilities’ impact, and finally devise countermeasures. We also discuss several possible use cases strongly connected to the railway industry reality.