Smaug first appeared in TA 2770 as a mature Fire-drake. I'm not sure if there are canonical sources which say his age or maturity, but he must have been quite large and quite old at the time in order to destroy the city of Dale and capture Erebor.
Since it is safe to assume that Smaug would have been attacking towns and stealing all of the gold and jewels he could get his claws on for most of his life, then he must have amassed a huge fortune prior to taking residence at Erebor. How did he transport his existing horde to Erebor? It seems unlikely that he would have simply abandoned all of his treasure that he had previously accumulated.
EDIT: It has been established that Smaug was not a mature drake at the time of his appearance. However, he may have already had a small horde (compared to Erebor).
Answer
In The Hobbit, Smaug specifically denies that he was "quite large and quite old" when he attacked Erebor and Dale:
"I laid low the warriors of old and their like is not in the world today. Then I was but young and tender. Now I am old and strong, strong, strong, Thief in the Shadows!"
(The Hobbit, Chapter 9, "Inside Information")
Thus it is quite possible that Smaug had no particular hoard of his own before the attacks. Thorin, after describing the wealth of the Mountain and Dale, states, "Undoubtedly that was what brought the dragon" (Chapter 1, "An Unexpected Party"). Thus, there would have been no need for him to transport gold and other treasure from the Withered Heath (or whatever particular place in the North he came from).
The real question, I believe, is the related "How did Smaug get the treasure of Dale from Dale to his lair under the Mountain?" We know that there were some such treasures (for example, the emerald necklace of Girion) which Thorin and Company found in Smaug's hoard. How did they get there?
This is a question which appears to have no answer in the canon. Unless Tolkien stated it in one of his letters, I am aware of no canon information bearing on it. The Hobbit simply accepts the presence of those treasures in the hoard as a matter of fact; and The Lord of the Rings (to the extent that it discusses the matter, which is at best minimal) does not investigate the question at all.
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