Ray Bittercress originally grew up as the only girl in a household which consisted of his alcoholic father, and four brothers. As a child lacking any sort of maternal figure in her life, Ray quickly grew up taking after her brothers, interested in swordplay, grand tales, and adventure beyond the borders of his little home in Combe. As a result, the other girls her age distanced themselves from her, regarding her interest in traditionally masculine pursuits as "queer", and driving her to further pursue those interests in defiance.

When adolescence came, Ray was forced to confront the harsh reality of being expected to settle down and marry "like a proper woman". Rebellious and tired of her alcoholic father and her brothers' increasingly changing expectations of her, Ray took to caring for horses at the local stable, and eventually convinced the stable-master to employ her as a stablehand. Yet, one by one, as her brothers married and moved out to start families of their own, Ray found herself taking on the burden of being her father's caretaker, something which she began to resent greatly.

Eventually, a chance encounter with the travelling knight Deschado ignited Ray's desire for freedom and adventure, and with her brothers' grudging permission, Ray was taken on as an apprentice under the knight. She would return more than a year later, coming up the Greenway and making a living guiding people throughout the North Downs and Bree-land.

Ray subsequently went on to marry the former Watchman Toddir Fairfield, to the surprise of many acquaintances and the rumour mill of Combe.