The trucks, many of them belonging to the Eddie Stobart haulage company, assembled on the Manston airstrip, which could be turned into a parking area under government plans.
The trucks then drove in a convoy to the port of Dover — a 20-mile (32-kilometre) journey — along a route that is far less used by lorries than the main highway from London.
The trucks drove around the port of Dover and returned to Manston for a second exercise later on Monday.
Letters to hauliers from the transport ministry said the test was aimed at ensuring “there is an effective plan in place should there be any disruption once the UK has left the EU”.
The use of the airfield as a holding facility “is one of the traffic management measures” in draft plans to “alleviate congestion” in the event of any disruption on the border, according to the ministry’s letters.
They also stated that officials would be using the exercise to “establish the safest optimum release rate of HGVs (Heavy Goods Vehicles) from the airfield to Dover”.
A transport ministry spokeswoman said 89 trucks were taking part in Monday’s exercise at a cost of 550 pounds ($700/610 euros) per driver or £48,950 for the whole fleet.
“We do not want or expect a no-deal scenario and continue to work hard to deliver a deal with the EU.
“However, it is the duty of a responsible government to continue to prepare for all eventualities and contingencies, including a possible no deal,” she said.
But Charlie Elphicke, the local MP for Dover, criticised the transport plan saying that it was “too complex” and likely to cause “enormous confusion” for lorry drivers.
Dover handles some 10,000 heavy goods vehicles every day and there are concerns that increased checks on the border will create congestion on roads in the county of Kent.
It currently takes only takes two minutes for a truck to complete the formalities.
A mere two-minute addition would cause traffic jams of more than 17 miles (27 kilometres) in Dover and similar chaos in Calais and Dunkirk, the Port of Dover warned on its website.