[Huinesoron]

C onspiracy - If three (3) is company, then what is five (4)?
U ndergate - Twixt dark below and dark above, below & between.
T hree Dwarves - + 60, -10, still stepping out of the same door.
T ower Hills - A place of first meetings, lingering glances, and (nearly) last farewells.
I mrahil - Twenty-second in the line.
N ob - A bit sweet, but backward, and if I gave a direct clue it would probably be crude.
G lorfindel - Elvish ... and a trio of Beornings.
R ed Arrow - Gondor calls, "The flaming cursor!"
O ld Forest - Not new, not two, not race, not safe.
O ld Man Willow - They could make almost a Hobbit sequel, but Warwick is necessary first
M an in the Moon - With a name, he's a stalker above all others; without his name, sing who he is.
F atty Bolger - Left behind; his namesake is on the Barrow-downs though.
L etter from Gandalf - Scrambled in an anagram: retained in the taproom.
O rald - Singular, lost in Ladros, in a house by the river.
O ld Took - Bilbo passed, and the Age removed
R angers of the North - Before they were grey, they served still.

[Theme: Things not in the Jackson movies.]

Both correct! 'Letter' is a nasty little clue because there's no actual anagram involved (I think you got it - what's scrambled in an anagram is letters). The Undergate (which Sam tries to follow the Orcs to) is a tricky one because barely anyone remembers it exists - but there's not many words starting with U! (Umbar was the obvious one, but the Corsairs are in there, so.)

Well done! Over to you, Pervinca.

hS