World-famous locomotive Flying Scotsman travelled alongside three modern trains to celebrate the "past, present and future" of Britain's railways.
The trains lined up on the East Coast Main Line at Tollerton, North Yorkshire, on Sunday morning before moving south to York.
Flying Scotsman was joined by an HST and InterCity 225 from Virgin Trains' current fleet, as well as one of the operator's new Azuma trains, which come into service next year.
Enthusiasts seeking to catch a glimpse of the trains were urged to remain behind safety boundaries.
Taxpayer-funded Network Rail was forced to pay out almost £60,000 in compensation when 59 train services were delayed by people encroaching on the track to get as close as possible to Flying Scotsman during its inaugural run in February last year following a decade-long refit.
Crowds gathered at York station to watch live footage of the event on a giant screen.
Rob McIntosh, a managing director for Network Rail, which is responsible for managing Britain's railway infrastructure, said it was a "prestigious and unique event for the people of Yorkshire".
He went on: "This was a long-standing vision for both myself and our industry partners and that vision has become a reality, creating a wonderful occasion to help us celebrate our proud rail heritage as well as the ongoing success of Britain's railways.
"To have achieved this truly special, once in a generation event with the eyes of the world watching - and to have not caused any disruption to regular rail passengers - makes me immensely proud."
The event took place when no regular services use that section of the line.
David Horne, managing director for Virgin Trains on the East Coast, said: "We're delighted to have presented this unique event showcasing the past, present and future of express rail travel in the UK, with our first Azuma travelling alongside Flying Scotsman and trains from our current fleet.
"With our new Azuma trains entering service next year, this has been an opportunity to celebrate the icons of the railways and look forward to 2018 when we'll usher in a new era for travel on the East Coast route."
Built in Doncaster, South Yorkshire, 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."