This one has always bugged me. Bilbo said "Today, I pass up the Old Took." and he was going through the Shire to get through the Grey Havens. Why didn't he go to Hobbiton to celebrate his 131st birthday, which, for all we know, could well have been a historic event given his great age? Also, it would have cleared his name, as they could then know that he didn't die in his "joke" 20 years earlier. BTW, I can't for certain, but, other than Gandalf, who himself had actually die once, was Bilbo by this point the only living member left of the quest to Erebor? (I know that Balin, Thorin, Kili, Fili, and two other of the dwarves had died already by this point and know that, sometime after the War of the Ring, Gloin passed away of old age and the others couldn't have been any younger either, as the two youngest, Kili and Fili, had died in the Battle of Five Armies.) Also, I believe that Dain Ironfoot was killed in the Second Battle of Erebor too (and so was Bard's grandson). (BTW, the wording of the Hobbit, it does appear that Bilbo did , at some point, die in the Undying Lands, because it says "To the end of his days, which were quite long, Bilbo......" meaning that he did die at some point. Was he so close to that point that stopping in the Shire one last time for a bit would have meant that he'd have died before reaching the Undying Lands? I just can't think of any practical for him not to have stopped there one last time. Leaving Hobbiton while the Ring existed was the right thing to do, but after it was gone, I don't see why he shouldn't have returned, at least to say goodbye, if nothing else. (At least I don't think that Mr. Bilbo Baggins was alive in the Undying Lands by the time that Sam and Gimili came, though Frodo might have been as he was about Sam's age.) Of course, Merry and Pippin chose to spend their last years in Gondor instead of the Shire, so maybe Bilbo's decision was just something personal like theirs was.