We are all rather used to pointing to Bilbo’s woeful unpreparedness when he sets off on his adventure one morning, long ago, in the quiet of the world when there was less noise and more green. And it’s absolutely a fair criticism. Bilbo not only runs out of his house without a hat, a walking-stick, or any money, or anything that he usually took when he went out. He also went without his pocket-handkerchief (imagine an adventure with no pocket-handkerchiefs!).
But we have to admit that, at least to his poetic mind, Bilbo had some idea of what an adventure might entail:
Then something Tookish woke up inside him, and he wished to go and see the great mountains, and hear the pine trees and the waterfalls, and explore the caves, and wear a sword instead of a walking-stick. [The Hobbit, Ch. I, ‘An Unexpected Party, emphasis mine.]
This is certainly more than we can say of Thorin & Co., if their provisions and preparations are anything to go by. Here are a group of dwarves who know full-well the danger into which they are heading. At least some of the dwarves recall first-hand the attack on Erebor, as Thorin recalls:
“The few of us that were well outside sat and wept in hiding, and cursed Smaug; and there we were unexpectedly joined by my father and my grandfather with singed beards.” [ibid.]
It seems unreasonable to suggest that Thorin, who saw the destruction of Dale and the slaughter of his kin, and whose ancestral home is deep within The Wild, would forget its many dangers. Yet they do seem to have done so. If not, then they must be either ‘selectively forgetting’ or else they anticipate any danger they may meet between the Shire and the Long Lake must be of such little concern as to not require mentioning:
We thought of going East, as quiet and careful as we could, as far as the Long Lake. After that the trouble would begin–.”
“A long time before that, if I know anything about the roads East,” interrupted Gandalf. [ibid]
Still, they had no weapons at all:
“If you come in peace lay down your arms!” said the captain.
“We have none,” said Thorin, and it was true enough: their knives had been taken from them by the wood-elves, and the great sword Orcrist too. Bilbo had his short sword, hidden as usual, but he said nothing about that. [The Hobbit, Ch. X, ‘A Warm Welcome’]
The only other weapons the company seem to have had were bows and arrows. But these were not brought with them when they set out. They were given to them by Beorn. And they were quickly rendered useless as they shot all their arrows whilst still within Mirkwood forest. This is just as well, since they would’ve been confiscated by the elves in any event, as was Orcrist.
Say what you like about Bilbo’s lack of preparation. But at least he daydreamed, albeit briefly, of carrying a sword. The dwarves clearly thought it far more important to bring along fiddles, flutes, clarinets, a drum, and a harp.