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My etymological answer would be Mayor Samwise Gamgee, using "climber" in the old-fashioned sense of social climber.

My non-etymological answer would be Gollum descending the Emyn Muil.

That didn't take long. Nicely done.

Coming back to this, my intended answer was the Stone of Erech. The text tells us that it was brought by Isildur out of Numenor at the time of the cataclysm. Think about that for a moment, and the...

Well, for all you young whippersnappers, this little ditty appeared in the Wormy comic strip that was at one time published in Dragon magazine when that periodical had not yet reached issue 100.

In land of mystic mountains grey
A time of folk since gone away
Fearsome foe noble hero slew
His wealth and glory greatly grew
Demand for precious treasure spurn'd
Name sire of slayer slain in...

On that point, I believe that at least some of JRRT's writings (perhaps not official canon) make reference to the Gate of Morning and Door of Night.

I am wondering if you were playing tricksy with us. How about the incident in Thranduil's halls where Bilbo stuffs the dwarves in barrels and drops them into the river through the trap door. ...

I believe the problem with Feanor as an answer is that it goes against the express instructions for the riddle. Wilros told us that the initial clue points to a second, intermediate clue, which then...

Henneth Annun by night?

Just so. You have the stick.

Hmm. That is a tough one. Not really "cargo" to my mind at that point in the story. Nor does the nature of its presence there quite reach the height of "absurd" unlikelihood to me. A very close...

Perhaps. Can you explain your answer?

Next one:

Absurdly unlikely cargo

I see this as something of a stretch given that the "waking" of Tulkas is not explicitly described in the text, but how about the implied rousing of Tulkas in the following passages:


Then Tulkas...

That would be "phantoms" plural. This is a single phantom. It is also a literal phantom, so no dice with any reference to the Woodmen's description of Gollum as a ghost in the night that drinks...

How about this:

Phantom

Far over mystic mountains crag,
Our comrades hither bit the bag.
Quite a group,
This travelling troupe.
Some were cousins,
Some were brothers.
Which of us
Weren’t like the others?

I know I owe three new riddles. Busy weekend with gardening and house painting. I will try to get the new clues posted soon.

Vilnas/Urias

Carn Dum?

[more letters]

Bilbo's silver spoons that Lobelia Sackville-Baggins "accidentally" dropped into her umbrella. Or was it her handbag? I don't recall exactly.

Turin waking up from the spell of Glaurung's gaze?

My inclination is to say "mallorn." I have some misgivings about that answer. First, I am not 100% certain that the canon texts made it explicit that the Lothlorien mellyrn derived from Laurelin in...

Bingo. You're up.

That's a great answer. If that doesn't work for Wilros, how about the Nimphelos? I don't recall whether it was black or not, but as far as I know it is the only "named" pearl in the books.