Ten cars from the South Eastern Vintage and Classic Vehicle Club in Essex took part in the parade, with cars dating back as far as the 1930s, when construction on the Dartford Crossing first started.
A Hydrogen Electric HGV from Tilbury-based Tevva led the procession, representing the fuels and vehicles of the future.
Cars included a Buick Series 40 Phaeton an MG PA from the 1930s and a 35th Anniversary Edition Mini.
The parade was waved off into the tunnel by Councillor Jeremey Kite, Leader of Dartford Borough Council.
The crossing, which turned 60 yesterday (November 18), is now used by 50 million vehicles over a 12-month period.
Speaking about the importance of the Dartford Crossing, Francis Cluett, Head of Delivery for National Highways, said: “It is important to celebrate the 60th anniversary of the first tunnel.
“It was an amazing engineering achievement at the time and had a huge impact on the communities either side of the Thames.
“Before it opened, the only means of crossing was by ferries – the tunnel has provided vital connections between people, jobs, and businesses for 60 years. Huge numbers of people have contributed over that time in planning, building, managing and maintaining the tunnel and it is time to recognize their achievement.
“We are working hard to ensure that the tunnel and other parts of the Dartford Crossing remain safe and operational for years to come.”
More than a billion vehicles are thought to have used the crossing since the first tunnel opened on November 18, 1963, according to National Highways.
The crossing was initially designed to carry about two million vehicles each year.
Due to increasing demand, an additional tunnel was constructed, which opened in 1980, and the Queen Elizabeth II Bridge opened in 1991.
Councillor Jeremy Kite, Leader of Dartford Borough Council said: “Since the opening of the first tunnel sixty years ago the Crossings has been an everyday part of the lives of local people.
“Today, as vehicle sizes and traffic volumes increase, Britain needs to show similar vision and get on with a new Thames crossing east of Dartford to relieve the pressure here and put the region’s economic potential back on track.
“Sixty years ago, opportunities to create crossings with the environmental features to make them cleaner and greener were far less than we have today.
“It’s time to get things started safe in the knowledge that we are doing the right thing for future generations.
“The same vision and determination which led to first crossing the Thames at Dartford 60 years ago is needed again now to create the modern Lower Thames Crossing”.
