Both Uses

although
in
The Two Towers
(Auto-generated)

The hobbits could see that Bregalad was now listening intently, although to them, down in the dell of his ent-house, the sound of the Moot was faint.†
Chpt 3.4

although = even though -- used to connect contrasting ideas
Then he lay on the ground, leaning out and looking down: but the light seemed to be fading quickly, although the sun had not yet set.†
Chpt 4.1 *

Definitions:

(1) (although)
even though -- used to introduce an idea that contrasts with or makes the main statement surprising

At the start of a sentence, although can play a role similar to words like however, yet, still, even so, on the other hand, or nonetheless—all of which signal contrast. In the middle of a sentence, although can sometimes be used where but or though might also work, but though or but often sound more natural. For example, "She's a great teacher, though not the most popular" is usually smoother than "She's a great teacher, although not the most popular."
(2) (meaning too rare to warrant focus)