There and Back Again

[Boromir88]

Originally Posted by Galadriel55

Also, I'm getting rusty, so I'm not 100% sure, but did he not visit the Lonely Mountain for a time while Frodo had the Ring in the Shire? He didn't settle down completely for quite a while.

He did get to Dale. I would imagine he saw the Lonely Mountain again, but doesn't seem like he visited:

'I got here without much adventure,' he said, 'and after a rest I went on with the dwarves to Dale: my last journey. I shan't travel again. Old Balin has gone away. Then I came back here, and here I have been.'...~Many Meetings

As for what Bilbo knew about the Ring and any danger he was in once settled in Rivendell:

'I hear all kinds of news, from over the Mountains, and out of the South, but hardly anything from the Shire. I heard about the Ring, of course. Gandalf has been here often. Not that he has told me a great deal, he has become closer than ever these last few years. The Dunadan has told me more. Fancy that a ring of mine causing such a disturbance! It is a pity that Gandalf did not find out more sooner. I could have brought the thing here myself long ago without so much trouble. I have thought several times of going back to Hobbiton for it; but I am getting old, and they would not let me: Gandalf and Elrond, I mean. They seem to think that the Enemy was looking high and low for me, and would make mincemeat of me, if he caught me tottering about in the Wild.'~ibid

[William Cloud Hicklin]

It seems, perhaps, dormitat bonum Homerus. Gandalf didn't know anything in particular about the Ring until he found the Isildur scroll at Minas Tirith in 3017, and then questioned Gollum in Mirkwood. Aragorn would have learned what Gandalf knew (or was willing to tell him) in the same time-frame; presumably he went straight from Thranduil's halls to Elrond's. In other words, that old ring of Bilbo's couldn't have caused much of a "disturbance" until roughly a year or so before the Council

[Inziladun]

In the broader scale, beyond just the Hobbits, none of the Fellowship is, at the end, in the same place as they were at the beginning of LOTR.

The Hobbits all die away from the Shire; Aragorn dies in Minas Tirith, though his 'home' was in Eriador; Gimli goes south from the Lonely Mountain and becomes Lord of the Glittering Caves; Legolas takes Elves from Mirkwood and goes to Ithilien.

Granted, with Gimli and Legolas, we don't know that they stayed in those new places, but Legolas did build his ship in Ithilien, with Gimli sailing away with him, as the tradition went.

Of them all, only Gandalf really went 'home'. That's especially noteworthy, since he was the only one of the Fellowship who could be said to have been homeless all during his time in Middle-earth.

[Kuruharan]

Originally Posted by William Cloud Hicklin

It seems, perhaps, dormitat bonum Homerus. Gandalf didn't know anything in particular about the Ring until he found the Isildur scroll at Minas Tirith in 3017, and then questioned Gollum in Mirkwood. Aragorn would have learned what Gandalf knew (or was willing to tell him) in the same time-frame; presumably he went straight from Thranduil's halls to Elrond's. In other words, that old ring of Bilbo's couldn't have caused much of a "disturbance" until roughly a year or so before the Council

Or Bilbo thought several times in the past year of going to get it.

[Faramir Jones]

This is an interesting thread, in terms of Bilbo's motivation for leaving the Shire for a second time in 3001 TA, this time for good.

According to what he said in Book 1, Chapter I, he first said to Gandalf, just before he left:

'I feel I need a holiday, a very long holiday, as I have told you before. Probably a permanent holiday. I don't expect I shall return. In fact, I don't mean to, and I have made all arrangements.'

He then said he was 'old', though he didn't 'look it'. He was 'beginning to feel it in my heart of hearts'. He felt 'all thin, sort of stretched', like butter scraped over too much bread. He then commented, 'That can't be right. I need a change, or something'.

He said he had made up his mind:

'I want to see mountains again, Gandalf - mountains; and then find somewhere where I can rest. In peace and quiet, without a lot of relatives prying about; and a string of confounded visitors hanging on the bell. I might find somewhere where I can finish my book.'

He also said to Gandalf:

'I want to see the wild country again before I die, and the Mountains; but he [Frodo] is still in love with the Shire, with woods and fields and little rivers'.

In Book 2, Chapter I, when the 4 hobbits got to Rivendall, and Frodo and Sam met Bilbo, the latter said to those two about his travels:

When he had left Hobbiton he wandered off aimlessly, along the Road or in the country on either side; but somehow he had steered all the time towards Rivendell.

He then said:

'I got here without much adventure, and after a rest I went on with the dwarves to Dale: my last journey. I shan't travel again....Then I came back here, and here I have been. I have done this and that. I have written some more of my book. And of course, I make up a few songs. And I listen and I think. Time doesn't seem to pass here: it just is.'

Near the end of LotR, in Book 6, Chapter VI, 'Many Partings', when the 4 hobbits visited Bilbo in Rivendell, he said that he had returned from his first journey 'by too straight a road'. But he admitted that if he had done so, the auction would have been over; and he would have had 'even more trouble than I did'. He then observed:

'Anyway it's too late now; and really I think it's much more comfortable to sit here and hear about it all. The fire's very cosy here, and the food's very good, and there are Elves when you want them. What more could one want?'

Looking at this, Bilbo's reasons for leaving appear to be:

1. Being very old but not looking old: He was aware that he was a very old hobbit, 111 years old, but certainly didn't look it, something he rightly felt was unnatural. He said to Gandalf that this conflict between how he felt and how he looked made him feel 'stretched'. Also, this was the subject of gossip, people being aware that there was something funny going on without knowing what it was. There was no reason why they should; because Bilbo and Gandalf weren't aware at that time of the Ring's true identity.
2. Peace and quiet: As a result of his age, Bilbo wanted to go somewhere for peace and quiet, without being disturbed by others, and where he would have access to the resources, both living and documentary, to enable him to write. He would also be well looked after, without being an emotional burden on Frodo and other hobbits he cared about. Frodo could also be his own master, in full control of Bag End.
3. To return to old places: Again as a result of his age, he wanted to look again at the places he had been to on his last journey before he died, which he did, going to Dale and the Lonely Mountain before settling in Rivendell. (I have an amusing picture of him being asked to open a new hobbit tea room in Dale or the Mountain! )

[Kuruharan]

Originally Posted by Faramir Jones

When he had left Hobbiton he wandered off aimlessly, along the Road or in the country on either side; but somehow he had steered all the time towards Rivendell.

I wonder what the dwarves who accompanied him thought of all this aimless wandering.

[Faramir Jones]

Presumably they were well aware that he was very old by hobbit standards, and would treat him as they would a very old and honoured dwarf, as long as he didn't put himself and themselves at risk. Perhaps they had orders from Dain to do this...

[Kuruharan]

Originally Posted by Faramir Jones

Presumably they were well aware that he was very old by hobbit standards, and would treat him as they would a very old and honoured dwarf, as long as he didn't put himself and themselves at risk. Perhaps they had orders from Dain to do this...

I was sort of being half joking.

I think that the dwarves held Bilbo in a degree of reverence that it was considered a honor to accompany him, especially since they eventually brought him to Dale.

[Galadriel55]

Originally Posted by Faramir Jones

1. Being very old but not looking old: He was aware that he was a very old hobbit, 111 years old, but certainly didn't look it, something he rightly felt was unnatural. He said to Gandalf that this conflict between how he felt and how he looked made him feel 'stretched'. Also, this was the subject of gossip, people being aware that there was something funny going on without knowing what it was. There was no reason why they should; because Bilbo and Gandalf weren't aware at that time of the Ring's true identity.

You know, this part, and the rest of your post, prompt the question if part of Bilbo's desire to travel around with Dwarves was an attempt to recall the "good old days" of adventure. But, of course, it's not the same, so he retires permanently to Rivendell.