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But half unknown to himself the regret that he had not gone with Bilbo was steadily growing. He found himself wondering at times, especially in the autumn, about the wild lands, and strange visions of mountains he had never seen came into his dreams.
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He LIKED walking in the autumn, and he got restless in the autumn. Bilbo left in the autumn, after his 111th birthday. I think it was at least partly sort of a ritual for Frodo, perhaps a hope that he might find him, or at least follow in his tracks. And the question that he asked Gildor that was most near his heart: "Tell me, Gildor, have you seen Bilbo since he left us?"
And actually, the example that Bilbo set for Frodo isn't the Unexpected party; Frodo wasn't alive for that. The example that Frodo saw, was the Long Expected Party, with its slow buildup and the giftgiving and the one last big celebration, and then the secret departure late on the day of his birthday.
And Frodo specifically did want to echo that. "What about the Autumn, on or after Our Birthday?" asked Frodo. "I think I could probably make some arrangements by then." (quote) Following Bilbo was uppermost in his mind, and the one thing that made the thought of leaving bearable.(/quote)
And Gandalf okayed it, reluctantly, but okay it he did!