My characters are, primarily, the parents of Merry, Pippin and Sam; Lotho and Lobelia Sackville-Baggins; with my main character being Esmeralda (Took) Brandybuck. I choose her for my focal point because she is closely related to three of the four Travelers: Merry, her son; Pippin, her nephew; Frodo, her cousin whom she may have helped care for after his parents died.
I have also chosen to have Sam's Mother, Bell, be alive at this time. Tolkien never mentions her as he does Sam's Father, Ham (the Gaffer), and so it would appear that she is not living at the time. He does mention the Gaffer being taken care of by a Widow Rumble after the Scouring of the Shire, however, there is no birth or death date listed for Bell in the genealogies.
I will be trying to follow the flow of events as Tolkien lists them as much as possible and hope you will overlook any times I go astray.
Once Upon A Time . . .
Her people had always been a temptation to the other peoples of the world. And so those others had claimed her people were myths, stories, beings who existed only in overly creative imaginations. Her people had wonderful fun with that notion, staying hidden in their woodland home rarely being seen or heard, as only mythical people can do, leading the others, when they came too near, off the paths that wound about through their woods until the outsiders were completely lost. Weaving spells round about the outsiders her people would enchant them, then return them to their own kind befuddled and starry eyed with the laughter of her people echoing forever in their minds.
The creature before her now intrigued her. She had not seen the like of him before. In height he was not much bigger than her people, but he was more sturdily built. He seemed to have a love of the trees and the flora of the forest floor as did her people. He moved without a sound, and his voice, when he spoke to himself, was quiet. How different from the bigger folk! She approached him with all the beguiling ways of her people.
They met once. They met again. As they met thrice, her fate was sealed. What had gone wrong, or gone right, she could never say, but she became enchanted by his gentle quiet ways as much as he was enchanted by her delicate, though sharp, features and clear green eyes. They pledged their undying love to one another and dwelt in woods that were claimed neither by his people nor hers, knowing neither would accept, nor truly believe, their joining. But they agreed that when their time in this world was no more, any offspring they had would dwell with his people.
So it came to pass. There is Fairy blood in the Tooks of the Shire.
"It was often said (in other families) that long ago one of the Took ancestors must have taken a fairy wife. That was, of course, absurd, but certainly there was still something not entirely hobbitlike about them . . ."
The Hobbit, An Unexpected Party J.R.R.Tolkien