Bycroft Freestone grew up in Bree, where his parents were researchers at the Scholar's Stair. They encouraged him to delve into the archives, and to study the history, literature, and science of Arda. Not content to stay within the stacks of books, he would spend hours in the Oldstone Ruins searching for shards of Cardolan pottery, or sitting in Jasmine's Garden, observing the way a snail would move across a rock. He'd marvel at the way subtle changes in the wind would influence the currents in the stream that ran past Greenway Crossing, or at the way he could set a dry leaf on fire by focusing sunlight through a broken ale bottle. His love of nature and science led him to seek instruction from Dalton Willow, who became his mentor, and one of his few friends. It was Master Willow who told him stories of the Elves of Rivendell, and their skill in harnessing the forces of nature.

When he was in his teens, his parents were called to Gondor, to help analyze ancient texts in the great library in Minas Tirith. Bycroft faced a choice: to follow his parents and aid them in their scholarly pursuits, or to stay in Bree and learn the ways of the lore-master from Master Willow. He chose the latter, and has spent most of the last decade either in the archives, or exploring the landscape around Bree, studying natural phenomena. It was while observing a partial lunar eclipse from a hillside overlooking the Midgewater Marsh that he was captured by bandits, and drawn into the struggle to defend Archet against the brigands who sought to destroy it.

Bycroft is at a turning point in his life as a lore-master and adventurer. When he was thrust into his role as a protector of Middle Earth, he did what was necessary to escape captivity and survive. Afterwards, he felt bound by honor to help Strider, and the others that had helped him. But as he continued his adventures, he became intoxicated by the excitement and the glory. Though he performed good deeds, his goal was to secure his future, and establish his reputation in his hometown of Bree. His adventures were simply that – adventures. While they were often harrowing and dangerous, his journeys never took him far from his home, or the places he felt safest – the Scholar's Stair and the Prancing Pony.

His recent journey into the Lone-lands, however, has led him to adopt a more global attitude. Seeing the hardships of the inhabitants and feeling their sense of isolation has shown him the future that his beloved Bree could face if the dark forces he's been fighting continue to thrive. He's become more focused on the responsibilities he bears as a lore-master, and on the role he can play in the ongoing struggle. While he once strived primarily to build a home with a library where he could pursue his arcane studies, he has now immersed himself in his role as protector, spending extended periods with the rangers in the North Downs, and the Eglain in the Lone-lands, and receiving guidance from Radagast the Brown.

One evening in Bree, while gathering supplies for a voyage into the Weather Hills, Bycroft was approached by a mysterious elf-maiden named Maudmuir, who invited him to join her kinship, the Keepers of Lothlorien’s Flame. Being welcomed into a kinship of like-minded adventurers, who share both a love of nature and a duty to protect Middle Earth from those who would corrupt it has strengthened his resolve. It’s brought him a sense of peace amid the chaos. It's also forcing him to overcome his shortcomings in the social realm. While he still feels more comfortable interacting with books and animals than with people, he now has more of a desire to be around others.  And his trips to the kinship’s home in Falathlorn have increased his desire to learn the ways of the elves, and to visit the elven lands of Rivendell and Lothlorien.