I love this chapter in all it's spooky, ghostly feel. And you just know despite Tom's warnings to steer clear of the barrows, or pass them on the western side, that the hobbits were going to be in trouble once they fell asleep on the "east side."
Twice Bombadil rescues the hobbits from the perils in the Old Forest, and when Tom says he must leave, we have the same feelings as the hobbits:
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All the same the hobbits wished he was coming with them. They felt that he would know how to deal with Black Riders, if anyone did. They would soon now be going forward into lands wholly strange to them, and beyond all by the most vague and distant legends of the Shire, and in the gathering twilight they longed for home. A deep loneliness and sense of loss was on them...
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The hobbits are leaving this 'alien' land, of which Tom Bombadil is a part of; he is Master within this forest (It'll be interesting to see possible connections to Treebeard in Fangorn). However, it's like a fantasy world, within a fantasy world. Remarkable how Tolkien does that.
We spend 5 chapters in the Shire, feeling like it's been fenced in and protected from the "real world." But as Gildor tells Frodo, the Shire is no longer protection for Frodo. The wide world outside knows about the Shire and has broken in. The hobbits decide to go through the Old Forest where they again leave the real world, and the threat of the Black Riders is put off for the time being. They get trapped in the dangers of this alien world, and are rescued by Bombadil, the Master alien himself. It seems weird to see a character who knows exactly what to do again Old Man Willow, and Barrow-wights, and the Ring has no power of him. We feel exactly like the hobbits "if Tom can handle all that, then surely he would know how to deal with Black Riders and the hobbits would be much safer with Tom." But, they wouldn't be. Tom is not the master of 'the Road,' the real world, that the hobbits must get back on. Tom is truly confined to his own borders.