Gandalf takes it upon himself to apprentice Frodo to the art of pity, but Bilbo appears to need no schooling in the subject - or is it that we simply never see the lessons taking place? Could it be that Bilbo (a lover of tales) began studying merciful behavior at the knees of gaffers and gammers whose local folklore reached back nearly a couple of centuries to the Long Winter of S.R. 1158? Gandalf later recalls that he had noticed the Shirefolk for their pity of one another in hard times.
Some of the saddest passages, however brief, in J.R.R. Tolkien's legendarium tell us of the merry, plump, and kindly hobbits perishing in this terrible climatic event. They have little reason to expect help from the outside world, but Gandalf's insight and pity impel him to come to their aid.
In painting this scene, which I have imagined taking place at the eaves of Woodhall, we see a band of desperate little hobbit hunters approaching the unexpected visitor in wonderment. Given the extreme conditions, I couldn't envision Gandalf arriving in a cart, but supposed he might have borrowed an old sleigh and horse from some trusted friend (perhaps Tom Bombadil?) Staves like "G" runes bear aloft blazing light, symbolic of Gandalf's service to the Secret Fire. Coming out from amongst the trees, the hobbits bear small, twinkling torches in answer. As I painted, I was thinking of the future in which the tiny lights within good hobbits will be joined to the great and bright purposes of this emissary from the Blessed Realm. A raven and a thrush perch in the bare branches, suggestive of adventures to come.
The fact that the details of the Long Winter survived to make it into written history suggests to me that Bilbo may well have learned about it as a piece of Shire lore and may have heard stories of how the hobbits tried to help one another in this catastrophe. Meanwhile, as far as I can understand from the texts, Gandalf's rescue of the starving hobbits appears to be one of his earliest involvements with them, and how must he have appeared to the weakened, sorrowful little folk! Imagine him emerging out of a blizzard with shining light and sacks, perhaps filled with grain. Gandalf begins to sound like a legendary folk hero - reminiscent of culture bringers like King Sheave - and I feel the folkloric quality of all this in the scene. From the very beginning, it seems, the wandering wizard was an exemplar of mercy amongst hobbits.
I can't really answer to my own satisfaction why Bilbo acted with instinctual mercy towards a hapless foe which Gandalf had first noticed amongst this Little Folk, while Frodo seems to have needed further tutelage. But, it's clear that the younger Baggins possesses all the capacity he needs once set on the right Road.
What I do think we can speculate about on firm ground is that Gandalf's actions during the Long Winter provide a memorable example of hobbit eucatastrophe. Everyone from Maia to hobbit is acting with pity. It's a story worth contemplating as a charm against despair. Some dark times feel as if they will never end, but Gandalf teaches Frodo to resist despair, "for even the very wise cannot see all ends."
If you find yourself having to tough out a very fierce season in your life or in your land, I highly recommend reading The Lord of the Rings as an endurance booster. We never know when or where a source of relief may suddenly materialize amid the storms, and it is always worth it to hang on. I sincerely hope this video short will give you encouragement from reflecting on the old and stirring tale of Gandalf offering lessons, by example, of the power of pity, to a folk with the gifts to appreciate it.