The development of the railways in Great Britain at the start of the 19th century was a time of great innovation in engineering, including infrastructure and rail vehicles under steam motive power. Unfortunately, it was also a time of some terrible accidents, including the fatality at the opening of the Liverpool and Manchester Railway in 1830 when Stephenson’s Rocket killed William Huskisson, and the Clayton Tunnel rail crash in 1861 where confusion over signalling led to 23 fatalities when one train ran into another in the tunnel. But, most importantly, lessons were learned from these dreadful events, leading to improved designs for locomotives and rolling stock, safer methods of working and operation, and new regulations and legislation. We are now at the dawn of autonomous road transport which offers the prospect of major benefits, not least in terms of a reduction in the number of road accidents and consequential fatalities. However, autonomous vehicles incorporate critical new technologies, such as machine learning, which could interact with unforeseen scenarios and manually driven traffic in unpredictable ways. This does mean that some residual accidents are inevitable. This paper considers a selection of railway accidents from the steam age and interprets them for the ‘autonomous age’, reading across to show how they can still be relevant and instructive.