The dwarves are just not all that organized. They don't seem to have gotten any clear idea, from either Gandalf or Beorn, how long the forest trek will take them, or how to get any food along the way. They don't even notice that Thorin is gone for almost an entire day, which shows how much of an effective leader he is that they do not. In fact, they might have done a better job of escaping from the spiders because Balin took over coordination, as he was better able to grasp Bilbo's plan quickly.
But really, they seem to have crept off into the forest in a quite disorganized fashion, when Thorin was still very much there. They could probably have done some sort of organized attempt to maintain contact with the path, if they had spaced themselves out between it and the first fire ring.
Bilbo, on the other hand, shows again the same pluck that he did when he was abandoned in the goblin tunnels and came face-to-face with Gollum. Probably for the same reason: there is no wizard to rely on instead. He seems to think ahead a bit more than the dwarves, and is also a lot more creative.
One does have to give the dwarves credit for grit, though, as they did a creditable job of fighting their way out of the spider mob even though they were starved, half-poisoned, and exhausted. But, again, why don't they all have good weapons? They knew the territory they would be going through would be dangerous. I suppose it's possible that some of them had weapons taken away by the goblins when they were captured. Gandalf got Glamdring back for Thorin, but he couldn't be relied on to grab everyone's weapons.
Hmmm...it is also peculiar that the Elvenking doesn't say anything about Glamdring when he is interrogating Thorin. Perhaps he hadn't recognized it yet? I wonder if JRRT actually explains about that later; I don't recall if Thorin had Glamdring during the later part of the story, I only know it ended up on his tomb after he was dead, but that could have been because the Elvenking gave it back.
All in all, it makes me wonder if the real reason Gandalf persuaded the dwarves to take Bilbo was not that they needed a burglar, but rather that they needed someone with sense, and he knew that they would not take kindly to him putting it that way. Certainly he seems to have finally parted ways with them shortly after Bilbo's escape on his own from the goblin caves, which was the first clear sign that he could act independently. Still, an awful risk to have taken, one wonders how many other times Gandalf sent a hobbit (or other innocent) off on a desparately dangerous adventure and it did not turn out so well. But then, given that he was an Istari, perhaps he was acting on inspiration of some sort to know that this was the right person and right time.
Chapter 9