A decision to cut the ferry route between Hull and Belgium has been described as the "end of an era" for the city.
Operator P&O Ferries said it was closing its service to Zeebrugge following a sharp drop in demand because of coronavirus.
Maritime historian Robb Robinson said Hull was losing another of its "connections with the Continent"
He described the decision as "damaging to the standing of the port".
Mr Robinson, who is a research fellow at the University of Hull, said: "It's very sad. "It's the end of an era.
"The purpose of the original settlement [Hull] was to trade with the Low Countries and literally the ferry is a modern example of the continuity of that trading and movement of peoples that's been going on for over 900 years or thereabouts."
"It really is psychologically, I think, quite serious damage in terms of that break."
The route, which has been running since the mid 1960s, has been described as loss-making by P&O and is expected to close in the next few months.
Two ferries, the Pride of York and the Pride of Bruges, will be taken out of service.
The 588 ft (180m) long vessels were recently refurbished and offer a daily service, sailing overnight across the North Sea.
David Hooper from the Hull and Humber Chamber of Commerce said he was "sorry to see the route go".
"It's going to have an effect on the business community," he said.
"I think the freight has continued largely unabated through the Covid crisis, but obviously the passenger side has tailed off somewhat with the drop in tourism.
"It was useful to have that service for the freight side of things and it avoids some of the chaos in Calais."
One ship sailing the route, the Norland, was requisitioned by the Ministry of Defence in 1982 as a troopship during the Falklands War.
It was involved in landing Royal Marines and other forces in San Carlos Water, where the vessel came under attack from Argentine aircraft.
Returning to service after the conflict the Norland continued in operation until being replaced by larger ferries in 2002.
One regular ferry user said he hoped P&O would "take another look at this decision".
Interpreter Daniel Pashley said he had fond childhood memories of the night crossing to Europe.
"We used to use it for family trips to the Continent," he said.
"In 2003 I started working in Belgium, so for as long as I can remember really it's been part of our family history."
"I would be terribly sad to see it go."