This is an important chapter. It is first of all the conclusion of the Hobbits' first journey, which occupies chapters 3, 4, and 5. It is also the last chapter set in the Shire until book VI (not counting the brief scenes in I. 11). And it is a chapter of some logistical importance - that is, it tells us who is going where.
Crickhollow is the third safe place we have encountered so far on the journey (the others being Woody End and Farmer Maggot's house), and in as many chapters. But each one of these safe places seems (to me, anyway) less safe than the last. With the Elves we fear no danger. Maggot certainly does not seem invulnerable; he is a fallible hobbit - but he is older and has a certain degree of authority. But at Crickhollow there is no authority figure, save Frodo (and Merry, I suppose). The danger has not really escalated all that much since the first encounter with a Black Rider. But the protection offered by the safe houses along the way has diminished.
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Rereading this chapter made me aware of the fact that it is Merry who has the greatest role in it.
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Each time I've read LotR I've realized more just how distinct the characters of Merry and Pippin are, even from the beginning. On earlier readings, I confess, I had thought of them as more or less identical - and I think this is the natural reaction of a lot of readers. But they are quite different. Pippin is a Took, Merry a Brandybuck - therefore Pippin has the Tookish curiosity and inclination toward adventure while Merry has the Brandybuck maturity. Pippin has a tendency to take up an adventure lightly, without worrying about maps and names and such things; Merry is little less likely to accept an adventure but is much more likely to do some research first. Pippin is a Hobbit of the Four Farthings; Merry is a Hobbit of Buckland and therefore knows a thing or two about the wider world. Merry has even been in the Old Forest. Pippin is altogether more like Bilbo and Merry more like Frodo - and this is no surprise, since Bilbo's mother was a Took and Frodo was raised in Buckland. Of course, Merry and Pippin are very similar in other ways. Both, after all, are inquisitive; and both are thoroughly Hobbit-like. The differences between them are very subtly drawn. This is a prime example to hold up in argument against those who criticize Tolkien's skill with characterization.
It's interesting that in chapters 3, 4, and 5 the party is made up of three, four, and five Hobbits, respectively. And in a sense in chapter 2 it consists of just two Hobbits - for it is there arranged that Frodo is to take Sam along. And this brings me to Fatty Bolger, one of those relatively minor characters that I am fond of for some reason unknown even to me. Perhaps it's because of the lack of recognition he receives - you'd be hard-pressed to find a reader that couldn't remember who Frodo or Sam or Merry or Pippin was, but I'll bet a lot of readers wouldn't remember Fatty Bolger. And yet he was in on the whole thing in the beginning just the same as Merry and Pippin. He even knew about the Ring! It's odd to think that while Gandalf is hiding the whole truth even from Theoden, and Denethor is just guessing it, there is away in the north in some hole or house in the Shire a Hobbit that knows all about the Ring.