This chapter is a long one and covers quite a bit of ground. For simplicity's sake, I've divided the chapter into 3 sections.
The Riders in Buckland
The first part of the chapter brings us back to Crickhollow and Fatty Bolger, who is still pretending that Frodo is holed up there to aid the Hobbits' flight through the Old Forest. However, this is the night that the Riders make themselves known and raid Frodo's house.
Silence descends on the house which must be strange considering how close it is to the Old Forest and it's many bugs and other noisy critters. Three shadowy figures enter the yard of Frodo's house and approach the door. As you can imagine, Fatty has bolted out the back door and is high-stepping it away as fast as his legs can carry him but the Riders don't know that.
They pound on the door, demanding that they open the door in the name of Mordor. A brave soul, indeed, is needed to refuse that.
Fatty has reached neighbors and began spreading the alarm. Word reaches Brandy Hall where the Master of Buckland (Merry's father) blows the Horn of Buckland to muster the Brandybucks and the other hobbits into a militia to repel the Riders.
Can you imagine this? Put yourself in the position of the residents of Buckland.
You've lived your entire life without hearing this horn, and most of your parents have never heard it either. Suddenly, in the middle of the night, a sound like rolling thunder blares over the hills, waking you and demanding your attention. Then, you are expected to heed the Master's call and appear, with pitchforks, clubs, whatever you might have, to repel the threat facing the land.
It's just a cool scene. Go re-read the beginning of this chapter.
Journey through the Marsh
The second part is more character development and historical fluff, detailing the departure from Bree and the slow slog through the Midgewater Marshes that separate Breeland from the barren lands guarded by Weathertop.
Frodo wakes the morning of their departure with a dream of hearing the Horn of Buckland. How does Frodo keep having these prophetic dreams? Tolkien has eschewed much outright magic, especially among those not of the older, nobler blood of the Elves (which includes the Numenorean men like Aragorn). Hobbits, Dwarves, and most men we encounter have no such proclivity.
Could these dreams be related to the Ring? My current favorite theory is that the Ring is acting a bit like a walkie-talkie here. Sauron is aware of who has the Ring but doesn't really know how to behave with someone else in possession of it (Isildur died and then it mostly disappeared. Gollum kept it in a pile and not always wearing it. Plus, it drove him mad). My theory is that these dreams are little bits of Sauron's experiences peeking their way into Frodo's head through the Ring. His dream here is about the Riders, who most certainly are intimately connected with Sauron and also fled from the Horn. Previously, he dreamed of Gandalf's escape from Isengard, which Sauron likely observed through the Palantir located there.
It's not a perfect theory, but I think its more plausible than Frodo somehow being a "seer" or something. Your thoughts?
Anyway, the party leaves Bree and they hit the road. Strider again speaks highly of his skills, boasting that he never takes the wrong path. Besides coming as a dismissal to Sam, it's important to remember that in the books, Aragorn is the one who argues against going to Moria the most. Gandalf convinces the others, however, and he reluctantly goes along. Turned out that Strider, indeed, never takes the wrong path. Willingly, at least.
They slog their way through the marsh and reach the barren, empty lands leading up to Weathertop. Frodo makes a crack while walking about losing so much weight, joking that soon, "I shall become a wraith". Strider is not amused by the joke, and this line is fairly prophetic to what happens at the end of the chapter when he is stabbed by a morgul blade and is in danger of becoming, you guessed it, a wraith.
I just noticed this line on the current read-through. Good stuff.
Storytelling and Conflict at Weathertop
The last portion of this chapter is dominated by two large history dumps, one about Gil-Galad, the last Elven High King, and the other about Beren and Luthien.
As they approach Weathertop, Strider explains this was once a great watchtower of the Northern kingdom and was where Elendil (Isildur's father) waited with his host for Gil-Galad and the Elven armies to join him on the march south to Mordor. Just when he is about to explain more about Gil-Galad, Sam bursts into song and sings a lovely ballad about the king.
Sam! As if we needed more reasons to like him, he sheepishly explains that he learned the song from Mr. Bilbo and memorized it years ago. Sam, our Elven scholar. Strider is also pretty impressed by Sam's knowledge of this ancient song and also impressed by Bilbo for having translated it. Bilbo must've been pretty busy the past 50 years translating all bits and pieces of Elvish history he could find.
Also telling because it shows that Strider knows Bilbo. Not surprising, really, but shows that Bilbo wasn't the "hermit" many of the hobbits believed him to be.
Secondly, while the party waits in the night for the Riders to appear, Strider sings them the ballad of Beren and Luthien. This is an abbreviated story that is told in much greater detail in the Silmarillion and is one of the deepest and most tragically beautiful stories Tolkien told.
I've written about it a bit previously, but Luthien was an elf (half-deity really, her mother was akin to Gandalf) and Beren was a lord of men. He fell in love with her and begged her father, King Thingol for her hand. He refused and set upon Beren an impossible task: retrieve a Silmaril from Morgoth (Sauron's boss). Beren, like a boss, puts his man-pants on and marches into Angband, and steals away a Silmaril from Morgoth's crown. It's kind of like the 12 Labors of Hercules if you are familiar with that story.
Anyway, then Strider goes on and on about their sons and daughters, stating the Elrond is a grandson of theirs and all the Kings of Numenor are descendents as well. Which, lets us know that Strider is of their blood and that story is especially touching since he is also in love with an elf whose father disapproved of the match. And also one where the elf chose mortality. And as a highlight, Arwen is also of their blood so its part of each of their legacies.
Again, not super relevant to this story, but super cool and worth a read.
Conclusion
Finally, we hit some action. The wraiths appear and Frodo, in his fright, puts on the Ring (at the Ring's urging...) He sees the Riders in their full and terrible splendor. He sees their long white hair with their leader wearing a full crown upon his head. This is big news if the Witch-King of Angmar himself has appeared. He stabs Frodo, showing that they can see through the Ring's magic (because they are in the spirit world and not the physical one mostly).
The wraiths only flee when Aragorn scares them away with fire. Well, shit. It's still over 10 days from Rivendell and we got a slowly dying important hobbit here.