Major-General Urquhart based his withdrawal plan upon the excellent evacuation carried out at Gallipoli during the Great War. The main feature of the plan, Operation Berlin, was to convince the enemy that the British were still holding their positions in Oosterbeek and intended to carry on fighting. Urquhart was quite certain that if the Germans suspected that the Division was pulling out then they would launch an immediate and violent assault along the River in an attempt to cut them off. With his troops out of their positions and falling back, it was vital that every ruse be employed to convince them otherwise.
To dissuade German patrols from venturing out of their trenches and discovering either evidence of the withdrawal or unexpectedly light resistance in the forward areas, the Light Regiment and the supporting artillery of XXX Corps put into effect a complicated fire plan to subdue the enemy positions. As there was precious little hope of evacuating them, Urquhart took the reluctant decision to leave the non-walking wounded behind, and those of them who were able to do so manned the abandoned positions to give the impression that the defences were unaltered. Most of the medical staff also remained behind to care for the wounded, also several radio operators stayed with their sets until a late stage to transmit a series of fictitious orders so that any Germans listening in would not be suspicious.
Stealth was vitally important, and so all the men blacked their faces, tied their weapons down and wrapped their boots in rags to dull any noise they might make. Any equipment that had to be left behind, such as radios, vehicles and artillery guns, were destroyed.
The withdrawal began after dark when the northern-most men, principally the 7th King's Own Scottish Borderers, silently left their positions and headed towards the embarkation point, closely followed by the next group. The defence proceeded to collapse in this manner throughout the night, with the northern-most troops leaving first and those to the south gradually falling in behind them. There were several of the British units, however, whose positions were so isolated that it was impossible to inform them of the withdrawal. "D" Company of the 1st Border, who had been effectively surrounded in the south-west of the perimeter (Map Ref 21) and reduced to just nineteen men on the previous day, were one such unit, and only five got away.
To steer the men safely towards the embarkation point, men of the Glider Pilot Regiment had marked out two routes with tape and also provided guides. Yet the route was by no means an easy one, and in the dark made worse by rain, several parties lost their way and were taken prisoner. There was no panic at the embarkation point. With the exception of the walking wounded, who were given priority, all ranks of the Division, from privates to generals, queued in the order in which they had arrived and calmly awaited their turn to cross. The ferrying operation began at 22:00, courtesy of the twelve powered boats of the 23rd Canadian Field Company, and the paddled assault boats of the 260th (Wessex) Field Company.
Due to a misunderstanding on their part, XXX Corps were under the impression that the 4th Dorsets had secured enough of the Westerbouwing high ground to enable the Division to also withdraw some of its men through this area. Almost half of the available boats spent the night at this crossing point, and they were collectively able to withdraw a total of forty-eight men, mostly Dorsets who had been in hiding since the previous evening. By the time that it was realised that the Division had no intention of embarking from this area, which had been firmly under German control since Thursday 21st September, it was too late for these boats to assist with the main evacuation.
Nevertheless, Operation Berlin was proceeding well. The sappers manning the boats suffered little interference for several hours, although the Canadians experienced numerous difficulties with the engines of their powered craft. Eventually the Germans became aware that crossings were taken place, but believed that they were carrying reinforcements north, not evacuating the Airborne troops south, and they responded by firing on the boats and shelling likely assembly points to the south of the Rhine. The sappers proceeded with the ferrying operation in spite of this fire, but as the night wore on both enemy action and engine malfunctions gradually reduced the number of Canadian boats in service. A number of passengers were killed or wounded during the estimated 150 crossings made by the 23rd Field Company during the night; the Canadians themselves losing seven killed and four wounded. The British sappers of the 260th Field Company, however, paddling the slow assault boats back and forth across the River, suffered no serious casualties during the evacuation, but their men became exhausted and required more hands, and consequently less passengers, to help with each trip.
As dawn drew near, most of those at the embarkation area had been evacuated, but with no more serviceable boats in operation, those that remained behind either had to surrender or brave the strong river and swim across. Stripping themselves off, most of those who chose to swim successfully made their way across, but the strong currents swept many of the exhausted men downstream, often washing them up into the hands of German patrols on the northern bank, and a large number of men also drowned. It has been estimated that ninety-five airborne soldiers died during the evacuation, and three hundred men, possibly far fewer, were left on the riverbank to become prisoners of war.
It was not until the following morning that the Germans began to appreciate what had taken place during the night. They began their usual attacks on the British positions at dawn, and were greatly surprised by the ease of their progress. The men who had stayed behind, as they had been ordered, laid down their arms and surrendered. Operation Market Garden was over.