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In The Hobbit cartoon Bilbo enters Lonely Mountain and confronts the dragon Smaug. Smaug is trying to figure out who he is and where he comes from. Bilbo answers in riddles about his many adventures to arrive at Lonely Mountain.

I come from under the hill.
And under the hill and over the hills my paths led.
And through the air.
I am he that walks unseen.
I am the lucky number, the web-cutter, the spider-stinger.
I am he that drowns his friends and draws them alive again from the water.
I am the guest of eagles, the ring-winner and luck-wearer...the clue-finder
...and the barrel-rider.

It is that last part that convinces Smaug that Bilbo must be from Laketown. As the barrels float down the river into the lake and are recovered by the men of Laketown.

Smaug has been asleep since he conquered Lonely Mountain, and Laketown was built up after he burned the existing human village to the ground. How does he know about Laketown, and that it recovers barrels from the wood elves?

I can't remember if these events are consistent with the book.

  • 1
    I don't think he's been asleep the entire time. But I can't canonically disprove it from memory – The Fallen Feb 21 '13 at 16:20
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The events are consistent with the book. Laketown was previously known to Smaug as Esgaroth.

“I don’t know if it has occurred to you that, even if you could steal the gold bit by bit—a matter of a hundred years or so—you could not get it very far? Not much use on the mountain-side? Not much use in the forest? Bless me! Had you never thought of the catch? A fourteenth share, I suppose, or something like it, those were the terms, eh? But what about delivery? What about cartage? What about armed guards and tolls?” And Smaug laughed aloud. He had a wicked and a wily heart, and he knew his guesses were not far out, though he suspected that the Lake-men were at the back of the plans, and that most of the plunder was meant to stop there in the town by the shore that in his young days had been called Esgaroth.

This is confirmed to an extent in Chapter 10 (A Warm Welcome):

Not far from the mouth of the Forest River was the strange town he heard the elves speak of in the king’s cellars. It was not built on the shore, though there were a few huts and buildings there, but right out on the surface of the lake, protected from the swirl of the entering river by a promontory of rock which formed a calm bay. A great bridge made of wood ran out to where on huge piles made of forest trees was built a busy wooden town, not a town of elves but of Men, who still dared to dwell here under the shadow of the distant dragon-mountain. They still throve on the trade that came up the great river from the South and was carted past the falls to their town; but in the great days of old, when Dale in the North was rich and prosperous, they had been wealthy and powerful, and there had been fleets of boats on the waters, and some were filled with gold and some with warriors in armour, and there had been wars and deeds which were now only a legend. The rotting piles of a greater town could still be seen along the shores when the waters sank in a drought.

It is possible that Smaug did not know that the Wood-Elves were trading with Laketown. But he deduced from Bilbo's riddle that he arrived on water and concluded that the Lake-men must have aided him.

“I thought so last night,” he smiled to himself. “Lake-men, some nasty scheme of those miserable tub-trading Lake-men, or I’m a lizard. I haven’t been down that way for an age and an age; but I will soon alter that!

“Very well, O Barrel-rider!” he said aloud. “Maybe Barrel was your pony’s name; and maybe not, though it was fat enough. You may walk unseen, but you did not walk all the way. Let me tell you I ate six ponies last night and I shall catch and eat all the others before long. In return for the excellent meal I will give you one piece of advice for your good: don’t have more to do with dwarves than you can help!”

10

Smaug hasn't been asleep for 150 years! He was flying around at least as recently as ~50 years ago and so had plenty of time to learn about Lake-town and their trade with the Wood-Elves.

... and some of the younger people in the town openly doubted the existence of any dragon in the mountain, and laughed at the greybeards and gammers who said that they had seen him flying in the sky in their young days.

--- A Warm Welcome, The Hobbit

1

Dragon's gotta eat sometimes...It was pretty desolate around the Lonely Mountain so his options were somewhat limited. He probably didn't fly too far south over the Elf base in the woods very often as they surely would have picked up on his vulnerable belly with their keen-eyed archers. I'd assert that he would certainly know of the general events going on around his immediate territory.

  • AFAIK Smaug wasn't aware of the chink in his armor, so that wouldn't factor into his decisions on where to fly. – TylerH Mar 17 '15 at 13:45
  • I didn't say he knew about it.. I said the elves would have likely seen it if he flew that far south, so he probably didn't fly that far south. He knew about events in his immediate territory but that is all. – Darian Miller Mar 17 '15 at 14:42

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