Did Boromir go through Bree on his journey to Imladris? Why? When?

Flammifer

Well-Known Member
Speculation again! Last class, there was discussion on whether Boromir passed through Bree on his way to Rivendell. There is not much evidence, but we can still speculate about the possibility, and, if he did, when might he have been there.

There are many possibilities. Here are some speculations, supported (thinly) by logic, and (even more thinly) by some sketchy evidence. There are certainly many more speculations about Boromir’s journey that might be just as possible.

What is known: Boromir went from Minas Tirith into Eriador via the Gap of Rohan. He then reached Tharbad, where he lost his horse fording the Greyflood. The journey from Minas Tirith to Rivendell took 110 days.

Initial thoughts:

  • Via Tharbad is not the most direct route from the Gap to Rivendell. Elrond, Gandalf, Hobbits and company (who know the way) just go north and slightly east from the Gap, up the west side of the Misty Mountains, returning from the War of the Ring. They take 28 days to make the trip mounted. But only 21 days of travel time, as they spend 7 days camped on the western side of the Mountains, saying farewell to Celeborn and Galadriel. Assumption: Boromir does not know where Imladris is, nor the best way to get there. He has gone too far west and is not on the best route.

  • From Tharbad, the best way to get to Rivendell is to go northeast, up the left bank of the Greyflood, Hoarwell, and Loudwater. No need to cross the Greyflood. Assumption: Boromir has not found good directions in or before Tharbad. He is heading across the Greyflood.

  • Why is Boromir crossing the Greyflood? Where is he planning to go once across? Assumption: He is planning to continue on north up the Greenway (Old North Road). However, this does not lead to anywhere near a likely ‘dale’, as these are found in mountains, and the road goes as far from mountains as is possible in Eriador. So, why?
Speculation: Possibly Boromir’s theory is that the ‘northern dale’, which Denethor mentioned, is in the Ered Luin? Boromir might have heard tales based on Cirdan and the Grey Havens, assumed that that was Imladris, and targeted the Ered Luin. Gondorian tales (based on the actuality of Cirdan) might suggest the presence of a very old and great lore master located somewhere in the Ered Luin. Dales are found near mountains. The mountains associated with Elves, and a lore master, in Minas Tirith might well be the Ered Luin (whence came Gil-Galad) rather than the western slopes of the Misty Mountains.

Assumptions: We know that Boromir has made extensive study of old battles, probably including the Battle of the Last Alliance. We guess that there are old maps of Eriador to be found in the archives of Minas Tirith. Boromir is an experienced general, who understands maps and the value of knowing terrain. We can assume he will have studied (and carried) maps of Eriador. It is likely that those maps will show the lands and territories of the kingdom (kingdoms?) of Arnor, the main geographical features of Eriador, and the main roads that existed when the maps were made. We can assume that Boromir did not find any maps which showed the location of Imladris (or he would not have gone to Tharbad, or, if he did, he would not be crossing the Greyflood).

Conclusion: Either Boromir is heading for the Ered Luin, or he is heading on up the Greenway for baffling reasons.

Assumption: If Boromir is heading for the Ered Luin, then from his maps, and from intelligence gathered in Tharbad, he is probably aware that his best route is to go up the Greenway until the road branches. Thence westerly, to cross the Brandywine at Sarn Ford, thence due west to the Ered Luin. If Boromir does not have an Ered Luin theory, then why is he crossing the Greyflood to go north up the Greenway? Where does he think he is going?

So, let’s stick with the Ered Luin speculation. Boromir, now on foot, heads towards Sarn Ford, and then towards the Ered Luin. This would explain why his journey took 110 days. Assume he reaches the Ered Luin, and begins exploring, looking for promising dales, or for intelligence. Assume that he gets intelligence, indicating that he is in the wrong place, on the wrong side of Eriador. Who could he have got such intelligence from? Possibly Dwarves, and possibly Elves. But let’s assume that he does get this unwelcome intelligence.

Now Boromir has a long way to go. Still, not so long as the distance from Minas Tirith to Tharbad. There are various ways he could travel: 1. Back past Sarn Ford to the Greenway, up the Greenway to Bree, east on the Dwarf Road. 2. Back past Sarn Ford, cut south of the South Downs, thence to the Last Bridge over the Hoarwell, avoiding Bree. 3. Head east, or north east, aiming to pick up the Dwarf Road near Michel Delving, thence east to Bree, through the Shire. 4. Head further northeast passing north of the Shire until hitting the Greenway between Bree and Fornorst, thence south to Bree.

There are not any good ways to head for Rivendell bypassing Bree to the north. There is a possible route bypassing Bree to the south. But, most routes from the Ered Luin to Rivendell lead through Bree, with the added incentive of probably being able to re-supply there.

Of course, if we discount the Ered Luin supposition, then Boromir would have just headed up the Greenway until he reached Bree (though hard to know why his journey would have then taken 110 days, and hard to know why he is avoiding Mountains and likely ‘dale’ locations).

So, there are many speculative routes Boromir could have taken from Tharbad to Rivendell, but, once he crossed the Greyflood, it is highly likely that he would have passed through Bree at some time.

So, if we assume that Boromir did pass through Bree, when?

What we know: We know that Boromir arrived in Rivendell at night on the 24th of October. That is 4 days after Frodo arrives in Rivendell, on the night of the 20th. Aragorn and the Hobbits have taken 21 days to travel from Bree to Rivendell. They are on foot, but have largely avoided the road, in favor of concealment in the hills.

Assumptions: Assume that Boromir gets re-supplied in Bree. He probably has gold (in his belt, purse, and boots) as an experienced campaigner would know enough to not keep all his resources on the horse that perished in the Greyflood. Even if out of money, Boromir is authoritative enough, confident enough, lordly enough, intimidating enough, persuasive enough, charming enough, to get re-supplied by one means or another in Bree. But, assume he cannot acquire a horse. (Barliman had a hard enough time finding a pack pony for the Hobbits). Boromir is on foot, with a fairly heavy pack. Still, he has been long delayed, so is pushing hard. He is very strong and fit. He is travelling on the road. He must be much faster than the Hobbits from Bree to the Ford of Bruinen. He might take some time to find Rivendell from the Ford of Bruinen, as the route is concealed, and not obvious. It could have taken him longer to find Rivendell from the Ford than it took Glorfindel, Aragorn and Hobbits. It took them only hours to get from the Ford (which they reached in the late afternoon of the 20th) to Rivendell (which they reached in the night of the 20th). (It also took Gandalf the Dwarves, and Bilbo, only hours to reach Rivendell from the Ford, as they crossed the Ford after noon, and arrived at Rivendell just as twilight faded into night, sometime in early June.)

Assume it takes Boromir 14-16 days from Bree to the Ford, and 1-3 days Ford to Rivendell.

I don’t think that Boromir arrived at the Ford earlier than Frodo, as he would have presumably got tangled up with Black Riders along the way.

I think the earliest he could have reached the Ford would be the day after Frodo, and possibly two or three days after Frodo reached the Ford. So, if he reached the Ford on the 21st, 22nd, or 23rd, then he might have left Bree between the 7th and the 9th, and arrived in Bree between the 4th and the 7th.

So, if Boromir came to Rivendell via Bree, it is likely that he arrived in Bree about 3-6 days after Gandalf left Bree, 4-7 days after the Hobbits left Bree.

Of course, he would have stayed at the Prancing Pony. Probably for 2 nights.

Conclusion: I think it is probable (though not certain) that Boromir passed through Bree on his way to Imladris. Possibly after a long detour towards the Ered Luin (though there are other possible explanations for the duration of his journey).

Inclinations favoring going through Bree: Once Boromir crossed the Greyflood, most routes (though not all) to Rivendell would go through Bree. Bree would be a good place for Boromir to re-supply.

Inclinations against going through Bree: At the start of the Council of Elrond, Boromir, ‘gazed at Frodo and Bilbo with sudden wonder’. If he had gone through Bree, he should have seen ‘halflings’ there. Would his ‘wonder’ at seeing Frodo and Bilbo have been so ‘sudden’ if he had seen Hobbits before?

Any other speculations on whether Boromir passed through Bree?
 
I have some thoughts.

1) Let's say Boromir set out from Gondor with literally no other knowledge specific to Rivendell than "some northern dale". What they probably DO have still in Gondor is some ancient knowledge of Arnor, and the means to get to it. Arnor was in the north... So, knowing that Rivendell is in "some northern dale" and also having a centuries out of date road map to Arnor, it might be reasonable to set out with the following plan: a) head toward Arnor, based on maps of old (ie. up the Greenway) b) this should get, if not to Rivendell, at least to a region closer to Rivendell where better directions can be gained, and c) then get ever closer to Rivendell with ever better/more recent directions.

(Aside: this is a daunting task, and one not certain to find success, as it relies on finding friendly help in an unknown region, but Boromir is suited for it I think, with his mixture of charisma and fortitude and will. In fact, the more I think about it, even though Faramir might have been the better man to actually sit at the Council and join the Fellowship, I think Boromir might have been the better man to actually get there in the first place.)

2) Timeline toward September/October. I just mentioned it in another thread, but I think Boromir could have spent *weeks* searching the area around the Ford to no avail, and only the increased traffic of Elves in the area out searching for signs of Frodo and/or the Nine would have led to him finding guidance into Rivendell. The Wild is large, and it's not ridiculous that he and the Nazgul may not have crossed paths in all that time - especially if he was way off track by the time the action really got hot, to the north perhaps in the Ettenmoors. Hey, it's a "northern" dale, so maybe he's too far north.
 
I just mentioned it in another thread, but I think Boromir could have spent *weeks* searching the area around the Ford to no avail, and only the increased traffic of Elves in the area out searching for signs of Frodo and/or the Nine would have led to him finding guidance into Rivendell.

I'm now picturing Boromir like Harry Potter at the train station wondering what to do next, until a family of Elves walks past and he happens to overhear the name "Imladris".
 
I don't think we're going to find any positive evidence that Boromir visited Bree. Though, as was said in class, I find the image of him at the Prancing Pony to be incredibly charming. I also don't think his look of wonder at the hobbits is proof he's never seen them before (taken by itself). He could have met some in Bree, and decided they weren't the type to appear in legendary houses of lore among such august company. Or, he could have heard rumblings of Frodo and co's rather shocking behavior--if he arrived after it took place--in which case he'd be full of something exceeding wonder to see hobbits (especially one who looks like Mr Underhill must have been described) showing up here.

Having said all that, this is (admittedly fun) fan fiction territory, and I don't think we can do more than speculate. (And even then, I don't find my own speculations convincing. "Wonder" is not likely how Boromir would have looked at Frodo, if he had heard of his Prancing Pony exploits.)
 
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Hi Amysrevenge,

If Boromir set out from Minas Tirith with no other knowledge of Imladris than 'some northern dale', why would he have gone into Eriador at all, rather than up the east side of the Misty Mountains?

Searching up the east side of the Misty Mountains (and maybe the Grey Mountains and the Mountains of Mirkwood) would have a certain logic. It is more directly north from Minas Tirith. There are probably tales of the Elves of Lorien in Gondor (we know from Eomer that there are such tales in Rohan). There might even be rumors of the Woodland Elves of Mirkwood in Gondor. If Boromir was just going off 'a far northern dale' and someone called 'Halfelven', then the east side of the Misty Mountains would seem a more likely place to search.

No, there has to be a reason that Boromir heads for Eriador. I don't think it is because he is targeting a dale on the west side of the Misty Mountains, because why wouldn't he then travel north along the western side of those mountains, looking for dales. He shouldn't go to Tharbad, and he certainly shouldn''t cross the Greyflood if he is thinking about Misty Mountain Dales.

Now, we know that Boromir is a student of past wars, campaigns and battles. There are two main wars involving Elves in the north that Boromir might have studied. The War of the Last Alliance, where Gil-Galad musters his armies in Lindon, then meets up with Elendil and his armies at Weathertop, before marching towards Mordor. This might have called his attention towards Lindon, and the Ered Luin. The second war would have been Earnur's campaign against the Witch King of Angmar, in which the armies of Gondor went by sea to Lindon, and then defeated the Witch King at the Battle of Fornost.

Earnur's war was 1,043 years before Boromir set out from Minas Tirith. The campaign maps from that war might well be the most recent detailed maps of Eriador held in the archives of Gondor. Those maps probably showed the Grey Havens and other Elvish places in Lindon and the Ered Luin. Accounts of the war would have mentioned Cirdan, as he led the host of Elves and Men of Arnor that joined the Gondorians to defeat the Witch King. After the battle of Fornost, Earnur pursued the fleeing Witch King eastward, and destroyed the rest of his retreating army with help from Rivendell, but the Rivendell contingent was led by Glorfindel, not by Elrond. So, the name 'Elrond' probably never made it into Earnur's accounts of the war, and the Gondorian map makers would have never got near Rivendell to include it in their maps.

I think it reasonable to assume that there were good accounts of this war in the archives of Gondor. Earnur went on to be King of Gondor, after all, so I'm sure his deeds were chronicled and preserved. Study of this war, accounts and legends about Cirdan as a great loremaster, maps showing havens in Lindon, and dales in the Ered Luin, could have all combined to produce Boromir's hypothesis that Imladris was likely in the Ered Luin.

Once Boromir crosses the Greyflood, it is hard to imagine that he is thinking about dales in the Misty Mountains. I think Boromir knows exactly where he is going. He is going to the Ered Luin and Lindon. He is following the right route to get to that destination. He thinks that that is where Imladris is, and he thinks that that is where he will find people who know where it is. If that is indeed where he goes, he proves to be half right.

Boromir travelling on foot all the way to the Ered Luin, and then back to Rivendell, would also explain why his journey took 110 days.

Of course there are other possible stories of Boromir's journey, but, for a story to be logical and likely, I think it has to fulfill three criteria:

1. It should explain why Boromir crossed the Greyflood.

2. It should explain why Boromir took 110 days to make a journey that should have taken much less time.

3. It should fit with the character of Boromir - smart, energetic, powerful, dedicated, experienced in wild country, good at reading terrain, in a hurry (he is needed in Gondor), prepared (he has whatever maps of Eriador that are available in Gondor).

So, stories like: Boromir was captured by agents of Saruman, and held prisoner for a long time before managing to escape, or: Boromir was harried and pursued by packs of wargs and driven far off his route before he was able to trap and kill all of them, would seem much more likely to me than stories such as: Boromir got lost, or: Boromir tarried along the way, or: Boromir was without provisions, so his progress slowed to a crawl as he was forced to hunt or forage for food.
 
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Now, we know that Boromir is a student of past wars, campaigns and battles. There are two main wars involving Elves in the north that Boromir might have studied. The War of the Last Alliance, where Gil-Galad musters his armies in Lindon, then meets up with Elendil and his armies at Weathertop, before marching towards Mordor. This might have called his attention towards Lindon, and the Ered Luin. The second war would have been Earnur's campaign against the Witch King of Angmar, in which the armies of Gondor went by sea to Lindon, and then defeated the Witch King at the Battle of Fornost.

You've missed a very important point here: The armies that met at Weathertop then went to Imladris, ere they made their final preparations before crossing the Misty Mountains and the Anduin to pass down the eastern bank of the river to Mordor. Isildur and his forces were making the return journey via the same path when the disaster of the Gladden Fields occurred. If the information you've listed was known in Gondor, there's no reason to believe that this other information wouldn't be.

So, on the basis of this information there are two ways to find Imladris:
A. Travel up the Anduin to the Gladden Fields and then strike west across the Misty Mountains looking for Imladris. Most of this path is through openly hostile territory either held or threatened by enemy forces.

B. Travel up the North Road to the junction with the Dwarf road to pass by Weathertop and head east to the foothills of the Misty Mountains to look for Imladris. This path would seem to be the safer way, with no enemy forces, and a road to follow.

Of course there are other possible stories of Boromir's journey, but, for a story to be logical and likely, I think it has to fulfill three criteria:

1. It should explain why Boromir crossed the Greyflood.

2. It should explain why Boromir took 110 days to make a journey that should have taken much less time.

3. It should fit with the character of Boromir - smart, energetic, powerful, dedicated, experienced in wild country, good at reading terrain, in a hurry (he is needed in Gondor), prepared (he has whatever maps of Eriador that are available in Gondor).

Path B explains his crossing of the Greyflood without sending him off to the Ered Luin.
His experience in wild country doesn't seem to be supported by the text: He admits that he's never crossed Rohan northwards before - so never been to Dunland - and the majority of his time seems to have been spent in the lands between Minas Tirith and Ithilien; Contested territory, but not wild. His ability to read terrain outside of his familiar range is similarly not proven in the text.

I also think you are unreasonably dismissing how much time would be consumed in hunting and foraging, and in finding a suitable place to spend each night and setup camp. Being an experienced general he would understand the significant difference between haste and speed.
 
Hi Anthony,

Where did you find information on the route the Last Alliance took from Weathertop to Mordor? I cannot find any suggestions on route when Aragorn talks about Elendil waiting for Gil-Galad on Weathertop, when Elrond talks about the Last Alliance at the Council, or in the appendices.

However, I sort of assume, in my supposition, that Information on the Campaign of the Last Alliance is thin and sketchy in Minas Tirith. For one thing, It all happened 3,019 years ago. For another, few survived. For third, people in Gondor did not take part in the march from Eriador to war, whichever route they took. So, while there might have been accounts in Gondor, who could have written them (except possibly Isildur, before he returned towards Eriador - and we know that at least some of what Isildur had written when he was in Gondor had, according to Gandalf, been, "unread, I guess by any save Saruman and myself since the kings failed.")

So, I assume that there was little detail, and mostly legends, known in Gondor about the War of the Last Alliance. (With at least some shreds of evidence to suggest that that is a possible hypothesis.)

I assume that there are more complete records and maps of the Earnur campaign against the Witch King in Eriador. Many people returned to Gondor from that campaign. Including a victorious King (well, Crown Prince, when he returned, but King later). Victorious Kings are wont to desire their victories chronicled and lauded. So, I hypothesize that Boromir derived much more detailed information from that campaign, which also, was only 1,043 years ago, than from the War of the Last Alliance.

On your suggestion of routes to travel to Imladris (if you know where it is) from the Gap of Rohan, there are two other routes:

A. Straight north up the western side of the Misty Mountains. The route that is taken by people who know the way, and know where they are going.

B. From Tharbad, up the left bank of the Greyflood, not having to ford the Greyflood (which was obviously dangerous) and considerably shorter than going up to Bree and then taking the Dwarf Road east (though shorter, but not on road). As for Boromir's skill in wild country, I base that mostly on his known generalship and campaigns in Ithilien. Ithilien has been deserted for 64 years, since 'the last inhabitants of Ithilien fled over the Anduin in 2954' (appendix B). So it is wild country, broken up by the foothills and dales of the Mountains of Mordor.

You are correct that your path B would explain him crossing the Greyflood (assuming that he was calculating that travel by road, even if considerably longer, would be better than travel cross country up the left bank of the Greyflood) if he knew where Imladris was. However, It would not really explain why it took him 110 days, and why he reckoned he covered 400 leagues.

I think your estimates of how slow Boromir might go, based on lack of supplies, are way too conservative. The average daily distance covered by through hikers on the Appalachian trail is 16 miles per day. They carry heavy packs. They have to find campsites, and set up camp, and they are hiking a trail not a road, with considerable more changes in elevation than the Greenway and the Dwarf Road. (Uphill really slows a hiker down.) Plus, we can assume that Boromir is tougher and fitter than 99% of them. Of course, hikers on the Appalachian Trail do not have to hunt and forage for food. But, neither, I assume, would Boromir, if he travelled this route. We know from Barliman Butterbur, that the Greenway is not deserted. Refugees and Slant eyed Southerners have been travelling up it. Boromir can resupply from them. Either by buying their surplus provisions, or by commandeering them. Boromir is on a vital mission for the realm! I think he will get his supplies without having to slow down by hunting and foraging very often.

Of course, if Boromir is heading for the Ered Luin, he should be able to resupply at Sarn Ford, and thereafter from the rich bounty in the Shire, for a while. If he reaches people around the Ered Luin who inform him of where Imladris is, he can resupply from them, and then from the Shire, and then from Bree.

Even if Boromir were extremely slowed down, if he were heading up the Greenway to the Dwarf Road, and thence to imladris, there is no way he could have travelled 400 leagues.

Boromir really cannot have travelled this way and both taken 110 days and gone 400 leagues, It is just not possible. Any credible account of Boromir's journey has to take him way off this route, just to get the distance in.

Judging by Eomer's comment to Aragorn, that Aragorn, Legolas and Gimili must have come 45 leagues in 4 days, and then estimating the distance from Minas Tirith to Rivendell via Gap, Tharbad, Bree, Dwarf Road (using the endplate maps), I would say the distance is about 225 leagues, or 675 miles. This is very far short of the 400 leagues, which Boromir reckons he travelled. Going all the way to the Ered Luin and back to Rivendell, would get him very close to the 400 leagues.

Sure, there are plenty of other stories of Boromir's journey that could take him 400 leagues and 110 days, without involving the Ered Luin, but I think that my story works pretty well, holds together logically, and has some sketchy evidence to support it.
 
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Looking at the maps, Boromir may have crossed the Greyflood to avoid the swamps of Swanfleet. From there, he may have marched north along the western bank of the Greyflood looking for the Last Bridge and/or the road to Amon Sul. That, although likely slower going in places than the Greenway, would certainly have been a more certain route — the Greenway disappearing in places in a way a river does not. Likewise, it is a more certain trade route for the region (akin to the way the Lake Men used the Forest River) and may have been able to travel part of it by boat or barge — which would be slow going, as they have to travel upstream (perhaps towed by oxen).
 
Hi Matt,

What map are you looking at? The map I am using (the fold out endplate map glued in to the back cover of my 1962 edition of both 'The Fellowship of the Ring', and 'The Two Towers'), does not show any 'swamps of Swanfleet'.

However, you are correct that going up the Greyflood (on either bank) would have been a shorter route from Tharbad than going via Bree. However, there are several problems with speculating that Boromir actually went this way:

1. This route is far shorter than the 400 leagues which Boromir (when leaving Lothlorien) says that he traveled to get to Rivendell.

2. It should not have taken him 110 days to get there by this route.

3. If fording the Greyflood looked dangerous (which it obviously was), why not just go up the left bank instead of fording it? (Other than the mysterious swamps of Swanfleet, of course.)

4. It sort of assumes that Boromir knew (at least roughly) where Imladris was. But, there is no evidence that he did.

If, for whatever reason, Boromir had arrived in Tharbad (and we know he did), going up the Greyflood, rather than through Bree would have been a shorter route, assuming he knew where he was going. However, both that route, and the route through Bree do not work with Boromir's estimate that he traveled 400 leagues, nor should they take anywhere near as long as 110 days to travel.
 
Thanks Matt for the info.

Although I am aware that there is some concern that the original maps (created, I believe, by Christopher Tolkien) are not perfect, I am dubious about how useful it is to use later maps of Middle Earth. The original maps are the ones that Tolkien was referring to when writing TLOTR.

Still, I am curious about what some of those later maps might indicate. If you used Aragorn, Legolas and Gimli's run from Parth Galen to near the fringes of Fanghorn as a yard stick, and called that distance 45 leagues (as estimated by Eomer), and then estimated the distance from Minas Tirith to Rivendell by 4 routes:

1. Minas Tirith to the Gap of Rohan, then straight up the western side of the Misty Mountains to Rivendell.

2. Minas Tirith, Gap, Tharbad, up the Greyflood to Rivendell.

3. Minas Tirith, Gap, Tharbad, Bree, Rivendell.

4. Minas Tirith, Gap, Tharbad, Sarn Ford, Ered Luin, Bree, Rivendell.

What distances would you estimate for each using the later maps?

The distances I estimate (using this somewhat inexact method) from the original maps are approximately:*

1. 245 leagues

2. 270 leagues

3. 315 leagues

4. 420 leagues

Do these distances make sense? Well, we know that Theoden and company travelled from Isengard to Minas Tirith, with a detour to Dunharrow in 10 days, and Elrond, Gandalf and Hobbits travelled from the Gap to Rivendell coming home, in 21 days travel time. So, it seems like travel by horse, at a steady, but not hurried rate, route 1 should take about 30 travel days. If route 1 is 245 leagues, is that reasonable?

It would imply an average daily journey of 24.5 miles. That would be a feasible rate of progress, especially if a few non-travel days, for rest of the horses, and re-supply, were added in. That equals an average speed of 3 miles/hour if travelling for 8 hours a day, 4 miles/hour if travelling for 6 hours per day. So, comparing the estimated distances, with the known travel times, the distances seem reasonable.

* These distances might not exactly correlate with previous distances I have estimated in this thread, as previously I used less precision in estimating, but this time I used a compass on the maps to get a better estimate.
 
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Besides the maps, we're missing another critical piece of info: Boromir says of Elrond's house, "of which many had heard, but few knew where it lay." Who are the many? And who are the few who knew meaningful directions? We might presume he asked around Gondor and Rohan, and queried a few refugees on the road, but that doesn't really tell us much. All we know for sure is that somewhere on the road he found someone who knew.
 
Boromir says of Elrond's house, "of which many had heard, but few knew where it lay." Who are the many? And who are the few who knew meaningful directions?
I always took this as mainly a rhetorical device of Boromir's. Just a way of saying "it was a real pain to find this place". I never thought of your questions before.

If those questions have any answers at all, I think the "many" are the elite of Gondor, and I still think that "few knew where it lay" is just his way of saying "I only got here after searching for a long and frustrating time". But it could very well also refer to the Gondorian elite: he implies that his father knew more than he would say.

I wonder if he did ask much along the way. I never got the impression that he met anyone at all on his journey. Certainly he was never able to replace his horse.
 
Besides the maps, we're missing another critical piece of info: Boromir says of Elrond's house, "of which many had heard, but few knew where it lay." Who are the many? And who are the few who knew meaningful directions? We might presume he asked around Gondor and Rohan, and queried a few refugees on the road, but that doesn't really tell us much. All we know for sure is that somewhere on the road he found someone who knew.

I imagine that Boromir asked many, in Dunland, Tharbad, Refugees and Squint-eyed Southerners on the Greenway, if they had heard of Imladris or Elrond or Half-elven. There were probably many legends in Eriador, so some of those names would be familiar, but none knew where to look. Saruman, of course, would have known, which is why it is a curious question as to why Boromir did not stop in Isengard on his way?

My speculation is that he did not get meaningful directions until he reached the Ered Luin, or the Grey Havens, where there would have been both Dwarves and Elves who knew where Imladris was.
 
How many sizable settlements *are* there in Eriador, west of the mountains? Could it be that Bree is the only such settlement east of the Shire, and that Boromir was headed to Bree for information since he had literally nowhere else to go? (Bree is the only such settlement shown on the map, but of course the map is biased towards showing those places that are of interest to us.) Then again, maybe Boromir didn't even know about Bree, and merely kept walking on the Greenway with the hope that he would eventually come across *some* town or another with information.

I had always been of the opinion before that Boromir came up along the mountains, because of what Boromir says before they go into Moria: "If we cannot cross the mountains, let us journey southwards, until we come to the Gap of Rohan…taking the road that I followed on my way hither." But I didn't know where Tharbad was at that point, which casts that theory into doubt. On the other hand, I have to wonder: did *Tolkien* know where Tharbad was when he drowned Boromir's horse there, or is this all retconning on our parts? :)
 
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