Why are Frodo, Sam, Merry & Pippin going into lands "wholly strange to them" when leaving Bombadil?

Question

The passage is from the end of "Fog On the Barrow-Downs" when the travelers are taking leave of Tom Bombadil. Tolkien writes:

They would soon now be going forward into lands wholly strange to them, and beyond all but the most vague and distant legends of the Shire...

yet in the opening pages of the next chapter, "At the Sign Of the Prancing Pony" Tolkien relates that

It was not yet forgotten that there had been a time when there was much coming and going between the Shire and Bree.

There are other passages as well that describe or allude to Shire residents visiting Bree.

So my question is, why are these lands just west of Bree "wholly strange to them" when by all accounts the Shire folk and the Bree population had a long history together, an ongoing relationship based on commerce and maybe even friendship? Tolkien seems to describe a part of the world no hobbit had ever set foot in when he says "all but the most vague and distant legends of the Shire" but apparently these lands are well-known and well-traveled by both Hobbits and Bree folk.

Answer 1

There's really no reason for Hobbits to travel east of Bree. The next settlement in that direction is Rivendell; which no 'respectable' Hobbit would have reason to visit. They would have to cross relative wilderness, a dangerous road just to get to an elvish city that most of them would mistrust anyway.

There's also the nature of Shire legends. Hobbits seem to prefer local lore, such as stories about Bullroarer Took or family histories, to the affairs of the wider world.

So, we have fewer Hobbits going to Bree, the lack of incentive to go east (and risk being considered as odd as old Bilbo), and the general culture of the Shire being less likely to retain stories of the outside world. Together, I think these factors could pretty easily result in the lands even a short distance beyond Bree being practically unknown.

Answer 2

Tolkien doesn't specify just exactly what these "lands strange to them" are; but from the fact that we're told they are "beyond all but the most vague and distant legends of the Shire", it seems reasonable to conclude that they are not the lands of or around Bree.

It's not explained precisely how Merry and Pippin came to know, but all the hobbits certainly know that their aim is Rivendell, of which they've all heard. None of them, though, not even Frodo, have actually been there or anywhere near; there's nothing in the books to indicate that even the Bree-folk had ventured far east of Bree, let alone anyone from the Shire. It seems most reasonable, then, to conclude that the "lands wholly strange to them" are the lands east of the Bree-land, up to Rivendell.

Answer 3

The lands east (and north and south!) of Bree have been wild and untamed for millennia. They were the wild lands that were beyond the knowledge of the Shire-Hobbits

Aside from the occasional Brandybuck or Bree-hobbit, and the odd adventurous Took, it was really only the Dwarves heading to the Blue Mountains, and Rangers like Aragorn that used the East Road west of Bree.

Dwarves had always used [the East Road] on their way to their mines in the Blue Mountains. They were the Hobbits' chief source of news from distant parts - if they wanted any: as a rule dwarves said little and hobbits asked no more.

--- The Shadow of the Past (The Fellowship of the Ring, Chapter 2)

 

"How far is Rivendell?" asked Merry...

I don't know if the road has ever been measured in miles beyond the Foresaken Inn, a day's journey east of Bree," answered Strider... "But I know how long it would take me on my own feet, with fair weather and no ill fortune: twelve days from here to the Ford of Bruinen."

--- A Knife in the Dark (The Fellowship of the Ring, Chapter 10)

There was simply no reason for anyone else to go east from Bree.

The North-Realm of Arnor had been destroyed over a thousand years before the War of the Ring, and its people had long since passed into legend for the residents of Bree and The Shire; featuring only in half-remembered sayings like when the King returns for an unlikely event.

Bree stood at an old meeting of ways; another ancient road crossed the East Road just ouside the dike at the western end of the village, and in former days Men and other folk of various sorts had travelled much on it. Strange as news from Bree was still a saying in the Eastfarthing... But the Northern Lands had long been desolate, and the North Road was now seldom used; it was grass-grown and the Bree-folk called it the Greenway.

--- At the Sign of the Prancing Pony (The Fellowship of the Ring, Chapter 9)

In fact, (aside from Bree) there were no settlements of men within 500 kilometres of The Shire. The Dunedain patrolled the wild lands that had once been Arnor, but they weren't telling tales of their exploits in Bree - they were talking of the old days, or bringing news from afar.

In those days, no other Men had settled dwellings so far west, or within a hundred leagues of the Shire. But, in the wild lands beyond Bree there were mysterious wanderers. The Bree-folk called them Rangers... when they appeared they brought news from afar, and told told strange forgotten tales which were eagerly listened to

--- At the Sign of the Prancing Pony (The Fellowship of the Ring, Chapter 9)

I suspect that this is both because of how they were perceived in the town, and also there was nothing to be gained from telling the Breelanders of the dangers that lurked in the empty lands that surrounded them