Science Fiction & Fantasy Stack Exchange is a question and answer site for science fiction and fantasy enthusiasts. It only takes a minute to sign up.
Sign up to join this community
In Chapter 7 of Book 6 of The Return Of The King, Homeward Bound, Barliman Butterbur compliments Gandalf's horse Shadowfax, saying:
"And you’ll be taking your horse to his stable yourself, Gandalf, I don’t doubt. A fine beast, as I said when I first set eyes on him."
When did Butterbur first see Shadowfax?
Did Gandalf find time to scout out ahead while the Hobbits tarried at Rivendell? He also seems to know a great deal about goings-on around the Shire.
When Barliman Butterbur says "...first set eyes on him", he is talking, as Daniel has pointed out below, about when Gandalf rides to Bree in search of Frodo, after escaping from Orthanc and passing through Rohan.
September
21 Gandalf meets Shadowfax, but the horse will not allow him to come near. He follows Shadowfax far over the fields.
22 Gandalf overtakes Shadowfax.
23 Gandalf having tamed Shadowfax rides from Rohan.
24 Gandalf crosses the Isen.
27 Gandalf crosses Greyflood.
28 Gandalf reaches Sarn Ford.
29 Gandalf visits the Gaffer.
30 Gandalf comes to Crickhollow, and reaches Bree at night.
The Return of the King - Appendix B: Tale of Years - 3018.
From the above, it would appear that Barliman first saw Shadowfax 9 days after Gandalf had acquired the horse, just after Frodo's departure. However they would've had more pressing issues to discuss than the beauty of the horse.
1 October
5 Gandalf and the Hobbits leave Rivendell.
6 They cross the Ford of Bruinen; Frodo feels the first return of pain.
28 They reach Bree at nightfall.
ibid.
Gandalf rode Shadowfax to Bree - via Hobbiton - after escaping from Isengard. As he describes to the Council of Elrond:
"Then I rode on in fear [on Shadowfax]. I came to Buckland [....] but it seemed to me that one or two had ridden towards Bree; and that way I went, for I thought of words that might be said to the innkeeper."
Chronologically, this encounter happens just after the hobbits themselves leave Bree with Strider. Barliman would definitely have seen Shadowfax then, and that's what he's referring to when he says "when I first set eyes on him".
Actually, I believe Butterbur may not have seen Shadowfax until Gandalf and the Hobbits came back to Bree on their way home to the Shire. Butterbur would have said "What a fine horse" to himself only a short time before he spoke to Gandalf. When the Hobbits and the Wizard left Bree, Gandalf peeled off and went to see Tom Bombadil, while the Hobbits went on to the Shire...where they found things not to their liking, and became involved in their last adventure.
