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."
10 scenic train trips in Europe
10 scenic train trips in Europe
The line between Glasgow and Mallaig is one of Britain’s most eye-catching train journeys. During the course of the 164-mile route, the “Road to the Isles” hugs the banks of Loch Lomond on departure from Glasgow, before making its way past castles, mountains (including Ben Nevis) and waterfalls en route to Scotland’s west coast. Then, just as you approach the journey’s end, the track crosses the spectacular Glenfinnan Viaduct, made famous by the Harry Potter movies.
There’s no disputing the Cote d’Azur is one of Europe’s loveliest coastlines, with golden beaches and bright blue waters stretching for more than 100km. Skirt the shoreline from Fréjus in France to Ventimiglia in Italy and you can give this sandy playground a closer inspection, because there are ample opportunities to stop and soak up the atmosphere if you catch one of the daily regional TER trains, which call at Cannes, Antibes, Nice, Eze and other stops along the way.
Keep your eyes on the skies on the daily InterCity from Venice to Munich, which weaves through the mighty Alps on the Austrian-Italian border. Following one of Europe’s great trade routes, the train calls at some of Italy’s finest Renaissance towns, before continuing to Innsbruck via the Brenner Alpine pass. The section between Verona, Bolzano and Fortezza is particularly striking as the train traces the river Isarco north in the shadow of the Dolomites, briefly crossing into Austria before arriving into Munich in time for dinner.
The narrow-gauge railway from Nice to Digne les Bains, in the Alpes-de-Haute-Provence region, is a relative unknown in the world of scenic trains. A 90-mile journey taking around three hours, it crosses rivers and passes through enchanting communities such as St Andre les Alpes and Entreveux. This is a private railway, so it often remains undiscovered unless you’re on a tour. However, it’s open for exploration by independent travellers, too, departing Nice CFP station four times per day.
A train trip doesn’t need to be long to be beautiful. The stretch from Messina to Catania in Sicily takes just 90 minutes, but the views of the coast and Ionian Sea are something to remember. If you’re travelling overnight from Rome, you’ll wake at daybreak to find the train being loaded onto a ferry. And from the moment you’re on Sicilian shores until your arrival in Catania you’re spoiled for choice – look east to see the rocky Mediterranean coastline and bobbing fishing boats, and west for none other than the peak of Mount Etna, Europe's tallest active volcano.
The joy of train travel is the transition from one place to another, watching the landscape unfold before you as you cross borders by rail. Starting out in Zurich’s cosmopolitan centre, this train quickly ascends into the Swiss Alps, passing green lakes, quaint villages, and snowy peaks. Just a few hours later you’ll descend into Italy, to the shores of Lake Como, catching a glimpse of the cupola of the cathedral and the lakeside villas bounded by Cypress trees. The Zurich to Como route is done on an everyday InterCity train, with no panoramic windows or fancy title to its name, yet it’s still a stunner of a trip.
The Golden Pass refers to the stretch of railway from Montreux to Lucerne in the Swiss Alps. Though feasible in a day, the route isn’t one to conquer in such a short time, and should be savoured. With countless opportunities to get off and explore, it’s easy to build your own itinerary on Switzerland’s famous scenic railways. The region is home to a host of scenic services, including glass-topped panoramic trains and funicular railways, so it’s little wonder that the Oberland attracts such wide praise from train travellers. Between Lucerne and Interlaken the landscape is exceptionally beautiful, passing the emerald-green waters of Lake Lungern and lakeside hamlets at the Brunig Pass.
Travelling at around 20mph, this scenic train is the epitome of slow travel. But although the Bernina “Express” hardly deserves its title, as it winds through the southern Alps, over bridges, gorges and precarious mountain passes, you wouldn’t want it to go any faster. Crossing some 200 bridges and passing through mountains via 55 tunnels, this is a feat of engineering so impressive that it has earned Unesco World Heritage status. The panoramic train has been designed to offer a ringside seat and as the rails mount the Albula pass to St Moritz, you won’t be disappointed by the views.
Fjords, glaciers and snow-capped peaks provide the spectacle on the Bergen Line, one of Scandinavia’s most impressive train journeys. Travelling from Oslo to Bergen in around seven hours, the trip’s highlights include Europe’s largest mountain plateau, Hardangervidda. But it’s not just the views that impress; the railway itself is extraordinary. More than 15,000 men laid this track into the peaks and dug 182 tunnels out of mountain rock, by hand. Construction started in 1875 – and took 34 years to complete.
An unexpected beauty in Spain, the train between Madrid and Oviedo offers a glimpse of classic Spanish countryside on its way from the capital to the north coast. And as the train approaches the Asturias region, and its principal city Oviedo, it climbs into the clouds, passing through the Picos de Europa mountains. Upon arrival in Oviedo, the train remains the best way to continue your explorations of the area: take a Feve narrow-gauge railway to Galicia and the Basque Country.