Tom Bombadil, unbeatable godclown who Sauron can’t touch, is just oozing such a metric tonne of whimsey at any given moment that the Wraith’s can’t even begin to properly penetrate the bubble of Chill Vibes emanating from the Shire 24/7 until their Master is basically at full power. See also why the Dunadine, mythical warriors from the times of old and teachers of the next King of Men hang out around the Shire because goddamnit SOMEBODY has to keep these adorable little weirdos safe.
I kid you not, the Dunadine just kind of hang out around the shire, keeping it safe.
This is also why, I think, in the book cannon when Saruman runs off to the Shire to hang out with his evil cohort hobbit for the rest of his life, who is a Sackville-Baggins I believe, he becomes a fun comedy villain nicknamed Sharkey by hobbits. Unless you are the literal Devil, you cannot penetrate the whimsy of the Shire because Tom Bombadil and his wife Goldberry are just too fun and powerful.
Also I’m pretty sure the Entwives are living in the Shire forests but I don’t know if Merry’s movie quote about there being a forest near the Shire where the trees grow tall and talk to each other is book-cannon. However, I maintain that that is why, at the end, Tom Bombadil is only interested in the parts of the adventure that involve the Ents because he’s like “holy shit I know where the Entwives are! HERE! My wife and I play Whimsy Bridge with them on thursdays hot damn I can finally bring the rest of the Ents here so they stop asking me to set them up with any sexy sapient bushes I know. Awesome!”
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