They took up the four tracks at Tollerton junction as they celebrated the history of one of the UK's most important routes.
The four trains were:
The Flying Scotsman
A Virgin HST (Class 43)
A Virgin InterCity225 (Class 91)
The new Virgin Azuma (Class 800) which will come into service in 2018
The four trains travelled side-by-side, in the same direction, at around 6am to celebrate the past, present and future of one of the East Coast Main Line.
They headed south together to York Station, where a giant screen had broadcast footage of the trains live.
Score of railway enthusiasts turned out to watch the event live.
Rob McIntosh, a managing director for Network Rail, which is responsible for managing Britain's railway infrastructure, said: "The area has a very proud rail heritage and by working closely with our industry partners we've been able to turn what has been a logistically challenging vision - to create an iconic railway moment on the East Coast Main Line without impacting on regular passengers - into a truly special occasion."
The event will take place when no regular services use that section of the line.
Built in Doncaster, in 1923, Flying Scotsman soon became the star locomotive of the British railway system, pulling the first train to break the 100mph barrier in 1934.
Paul Kirkman, director of York's National Railway Museum, which owns the locomotive, said: "The East Coast Main Line has long been famed for speed and style. "In the 19th century elegant locomotives were designed to haul trains on this route, cementing its reputation as a railway racing stretch operated by thoroughbred engines.
"The four-train line-up epitomises the evolution of the later generation of fast, elegant and stylish trains - all with a shared bloodline - that epitomise the history of the route from the 1850s to today."