Dan had this to say about his inspired drawing:
The drawing of ‘Frodo walking under Starlight’ is taken from a paragraph near the beginning of ‘The Shadow of the Past’, the second chapter of The Fellowship of the Ring.
Frodo went tramping over the Shire with them; but more often he wandered by himself, and to the amazement of sensible folk he was sometimes seen far from home walking in the hills and woods under the starlight.
To set the context, the first chapter ‘A Long-Expected Party’ ended with Bilbo’s disappearance at the Party, his confrontation with Gandalf later in Bag End about actually leaving the Ring behind, Bilbo’s departing from the Shire, and Frodo’s discovery that Bilbo had left him the Ring.
The next day, in response to Gandalf’s questions, Frodo said that he knew nothing more about the Ring than what Bilbo had told him. Gandalf in turn warned Frodo that he had begun to have fears about the Ring and urged him not to use it, at least in any way that would cause talk or arouse suspicion, and to ‘Keep it secret, keep it safe!’
Then to Frodo’s dismay, Gandalf informed him that he would be going away immediately, but that he would return to visit him when he could. When he returned he said he hoped to have more information. The last line in the chapter says that Frodo did not see him for a long time.
In addition to this parting from Gandalf is the backdrop of Frodo’s life with Bilbo at Bag End. To my knowledge, there is no specific age mentioned at which Frodo became an orphan other than that he was a child. Soon after, Bilbo adopted him and brought him to Bag End, where he no doubt grew up hearing about his famous Uncle’s adventures.
Bilbo’s knowledge of the outside world became part of his upbringing. He learned of Dwarves, Elves, Trolls, distant places and remote events. He learned something of the history of middle earth and a bit of the Elvish language.
Later, when Frodo heard Gildor and his companions singing on the road near Woody End he recognized that they were ‘High Elves’ because they spoke the name of Elbereth. Because of this one would have to assume that he knew something of Valinor, the Valar and the return of the Noldor to Middle Earth.
It is in this frame of reference that I read in the opening paragraphs of ‘The Shadow of the Past’ some information about Frodo.
It states than ‘In the years after Bilbo’s departure from the Shire, Frodo began to carry on Bilbo’s reputation for oddity. He refused to go into mourning and each year gave Bilbo a Birthday Party. ‘
Also, that he lived alone, as Bilbo had done; and that he had a good many friends, especially among the younger hobbits, but his closest friends were Peregrin Took and Merry Brandybuck.
But especially – that Frodo went tramping over the Shire with them; but more often he wandered by himself, and to the amazement of sensible folk he was sometimes seen far from home walking in the hills and woods under the starlight.
It states that Merry and Pippen suspected that he visited Elves at times – as Bilbo had done.
To me these are all windows into Frodo’s character. His information of the outside world was probably very incomplete, but if one knows the name of Elbereth who wouldn’t want to walk alone under the stars at night and wonder about the Star-Kindler, and the One who taught her the music?
He was nearly alone in the Shire with his knowledge of the outside world, and Gandalf’s dark hints about the Ring no doubt weighed on his mind, and yet he was a hobbit – he loved the Shire, the quiet life, and the comfort of Bag End.
He didn’t realize it yet, but he had a high destiny ahead of him that would place him in a very select company of heroes in the history of Middle Earth.
All this is to conclude that during the 16 or 17 years between Bilbo’s departure and Gandalf’s return with a way to test the ‘One Ring’, Frodo had plenty to think about. Apparently alone, under the starlight miles from home, was one of the best ways for him to do it.
They say a picture is worth a thousand words, and this ‘picture’ is what I have had in my mind for some time with all of these thoughts behind it.