Fatty Bolger
 

During the discussions that took place between the hobbits the night they stayed at Crickhollow, it was stated that Fatty Bolger had "never been over the Brandywine Bridge".

Fatty came from the Northfarthing, but assuming he was in Buckland often, surely he must have done so at some stage, even if only to quickly cross the bridge then turn right through the Buckland North Gate? Or did he always go miles out of his way and use the Buckleberry Ferry?

My understanding is that Fatty had always been a homebody who stayed near Hobbiton, never before venturing as far afield as Buckland. So at Crickhollow, he was out of his element. I could be wrong, but that's how I always understood it.

Is it taken for granted that he had been over the River before helping Frodo move?

If he was closer in friendship with Frodo than with Merry, I think it's plausible that the trip to Crickhollow might indeed have been his first time over the Brandywine.

x/d with elempi

I'm ever the un-perfectionist when it comes to those things. It couldn't have worried me less if Fatty Bolger in fact has crossed the bridge on some occasion long ago. The point that this statement is trying to make is that, as Elempi and Inzil have already said, Fatty is completely out of his element going even as far as Crickhollow - forget about venturing into the Old Forest! I just always placed more importance on the general message than on specific details.

I would be surprised if many hobbits (outside those who had connections in Buckland) had ever crossed the Brandywine river. In the discussion in the Ivy Bush Tavern, both Daddy Twofoot and Gaffer Gamgee mention that it is queer folk who live in Buckland. I would suggest that this sort of prejudice was formed through not having met any Bucklanders, supporting the idea that very few hobbits would have crossed the Brandywine, not just limited to Fatty Bolger.

Gaffer Gamgee is a neighbor of Frodo Baggins, who lives at #3 Bagshot Row, and shows a high respect for Frodo Baggins, though Frodo is a half a Brandybuck and was born and in his early years raised in Buckland. Gaffer Gamgee quite possibly also personally knows Merry Brandybuck who is a close personal friend of Frodo’s and often a visitor at Bag End.

Fredegar’s home territory, according to “A Conspiracy Unmasked”, was the Eastfarthing, “from Budgeford in Bridgefields in fact, but he had never been over the Brandywine Bridge”. However we learn in “A Conspiracy Unmasked” that of the original company of Frodo, Sam, and Pippin, “Sam was the only member of the party who had not been over the river before.” And there is no hint that either Frodo, Merry, or Pippin had ever been to Bree before, and so had presumably also never been over the Brandywine Bridge previously, unless we are to imagine that they had at least once crossed the Brandywine Bridge as a convenient entry into Buckland by the East Road, rather than by Buckleberry Ferry.

Indeed it is implied, though not explicitly stated, that Fredegar and Merry had originally traveled with a wagon load of Frodo’s household possessions to Crickhollow by the East Road and the Brandywine Bridge. If this interpretation is correct, then Fredegar had used the Brandywine Bridge to get to Buckland and to Crickhollow where he is later found.

Wayne G. Hammond and Christine Scull in their The Lord of the Rings: A Reader’s Companion, page 119, suggest that readers who complain about Tolkien’s wording here are being over literal. They write:

Fatty is now in Buckland, east of the Brandywine, but he has certainly been on the west side of the river, since he was present at Bilbo’s party (indicated in Appendix C) as well as at Frodo’s birthday dinner at Bag End only a few days earlier, and earlier ‘often in and out of Bag End’ (Book I, Chapter 2, p. 42. I: 51). It seems unlikely that Tolkien meant to suggest that Fatty always crossed the river by the ferry, and not the bridge; presumably these words are meant to convey that he had never traveled further East on the Road than the Brandywine Bridge, beyond which is the wide world.

Tolkien should in theory have written something like (italics mine):

… “from Budgeford in Bridgefields in fact, but he had never been over the Brandywine Bridge, save only to gain entry to Buckland.”

Tolkien and Aristotle
 

Your wishing Tolkien could have written something as you suggested, jallanite, reminds me of how all of us have wished he were still around, or brought back to life, so we could ask him about this and many other things. However, I think it's just as well things are as they are, for this reason.

In Part 1, Chapter 1 of Miguel de Cervantes' Don Quixote, published in 1605, the small squire of the title went mad with all his reading of knightly romances, and trying to make sense of what was in them:

Over conceits of this sort the poor gentleman lost his wits, and used to lie awake striving to understand them and worm the meaning out of them; what Aristotle himself could not have made out or extracted had he come to life again for that special purpose.(My italics):)

So even the great Greek philosopher would have been confounded by the problems being wrestled with by Don Quixote!:D Might Tolkien have, had he been brought back to life, been equally confounded by the problems argued over by us fans?;)

^ Amen. This is after all a novel, not the Talmud.

^ and amen to that as well!