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Hiding behind one of the largest barrels Bilbo discovered the trapdoors and their use, and lurking there, listening to the talk of the king's servants, he learned how the wine and other goods came up the rivers, or over land, to the Long Lake. It seemed a town of Men still throve there, built out on bridges far into the water as a protection against enemies of all sorts, and especially against the dragon of the Mountain. From Lake-town the barrels were brought up the Forest River. Often they were just tied together like big rafts and poled or rowed up the stream; sometimes they were loaded on to flat boats.
When the barrels were empty the elves cast them through the trapdoors, opened the water-gate, and out the barrels floated on the stream, bobbing along, until they were carried by the current to a place far down the river where the bank jutted out, near to the very eastern edge of Mirkwood. There they were collected and tied together and floated back to Lake-town, which stood close to the point where the Forest River flowed into the Long Lake.
For some time Bilbo sat and thought about this water-gate, and wondered if it could be used for the escape of his friends, and at last he had the desperate beginnings of a plan.
The evening meal had been taken to the prisoners. The guards were tramping away down the passages taking the torch-light with them and leaving everything in darkness. Then Bilbo heard the king's butler bidding the chief of the guards good-night.
"Now come with me," he said, "and taste the new wine that has just come in. I shall be hard at work tonight clearing the cellars of the empty wood, so let us have a drink first to help the labour."
"Very good," laughed the chief of the guards. "I'll taste with you, and see if it is fit for the king's table. There is a feast tonight and it would not do to send up poor stuff!"
When he heard this Bilbo was all in a flutter, for he saw that luck was with him and he had a chance at once to try his desperate plan. He followed the two elves, until they entered a small cellar and sat down at a table on which two large flagons were set. Soon they began to drink and laugh merrily. Luck of an unusual kind was with Bilbo then. It must be potent wine to make a wood-elf drowsy; but this wine, it would seem, was the heady vintage of the great gardens of Dorwinion, not meant for his soldiers or his servants, but for the king's feasts only, and for smaller bowls, not for the butler's great flagons.
Very soon the chief guard nodded his head, then he laid it on the table and fell fast asleep. The butler went on talking and laughing to himself for a while without seeming to notice, but soon his head too nodded to the table, and he fell asleep and snored beside his friend. Then in crept the hobbit. Very soon the chief guard had no keys, but Bilbo was trotting as fast as he could along the passage towards the cells. The great bunch seemed very heavy to his arms, and his heart was often in his mouth, in spite of his ring, for he could not prevent the keys from making every now and then a loud clink and clank, which put him all in a tremble.