Millton Oldwine was born to Sediment Oldwine and Myrtle Hatcarry 50 years ago, before the war of the Ring, in Brandy Hills. His family later moved in Hobbiton, raising Millton there. His father Sediment was a farmer, brewing a family wine and selling it to the local hobbits. Even though Sediment was a farmer as well, he was quite wealthy for one of his kind. It was told that an ancestor of his, from his father's line, used to be an explorer who reached the lands beyond Bree. Nobody knows how he got the treasure, but the people in his family say that when he was in the barrow downs, during one of his adventures, he found many treasures, after his encounter with dark creatures, which he didnt dare to talk about.

As a young lad Millton was raised listening the stories of mr. Bilbo Baggins. He was fascinated with mr. Bilbo and loved his tales. They were the spark who woke up the adventurer deep inside him. Unlike the rest people of the Shire, Millton believed that mr. Bilbo is not a madman, but infact a great and noble hobbit. Not long after the disappearance of Bilbo, Millton, as a hobbit, who recently reached adulthood (33 years), he decided to leave the Shire for a while and go on an adventure, exploring the world just like his ancestor, who was his great-great grandfather.

Millton, apart from being an adventurer, was far more than that. He was, infact, a musician, mastering the art of the lute. He was also a gifted singer, being taught how to sing by his mother since he was able to say his first words. While growing up, Millton loved singing with his friends, going to the "Green dragon" and rising up the mood of the local people. The hobbits loved Millton, but when they found out that he disappeared like Bilbo did, they were shocked.

The first thing he decided to do during his first adventure was to go Buckland to see his second cousins. There he stayed at the home of his best friend Stanford Hillbuck, who was his second cousin by his mother’s line, for 2 days. Millton revealed to Stanford about his desire to go beyond the Shire on an adventure, to see that the world is wider than he thinks, that there’s far more to see than the farms and the hobbits. Stanford was a hobbit who once or twice in the year was visiting the village Bree, listening to all kind of rumours and stories. He was hungry to see the world, but he never dared to go alone.  Stanford asked to accompany Millton to his adventure. Millton agreed and their first destination was the old forest, which was east from Buckland. The two hobbits entered into the forest after the night. Even though they could have traveled during half of the day, Stanford adviced Millton that’s it would be better if they traveled during the day. Despite the rumours, Millton was rather more curious than scared from what he heard about the rumours. 

The two hobbits travelled through the forest. Luckily, it wasn’t Stanford’s first visit in the forest. Infact he was often going in it. There they met Tom Bombadil and Goldberry. Tom was a friend of Stanford and later a friend of Millton. They stayed there for three days as guests, hearing all kind of interesting stories from Tom.