Drucilla, also known as "Cill", was the third of six children born to Abijah and Lucy Terry Prince, both of whom had once been enslaved. The Princes were married in Deerfield, Massachusetts, and all of their children were born there. Sometime after the birth of their last child in 1769, the family moved to Abijah's land in Guilford, Vermont.
When she was in her early 20s, Cill moved back to Deerfield and worked in the tavern of David Hoyt. He also kept a store where she had an account. Some of her purchases included fabric, sewing notions and paying someone to sew for her, shoes and repairs to them, a snuff box, a handkerchief, flour, salt, Indian corn, rum, and molasses. Her work in the tavern covered the costs of most of her purchases. Cill didn't stay longer than about a year in Deerfield. David Hoyt noted in his account book that "Cill Prince went home the twenty first Day Novemr 1783."
By 1790, Drucilla was back in Deerfield, but must not have had a source of income, for on July 19, she was "warned out" of town. In New England, rather than be burdened with the expense of providing for people who could not support themselves, the town administrators ordered them to leave. Drucilla once again returned to her family in Guilford.
The Princes also owned land in Sunderland, Vermont, and after Abijah died in 1794, Drucilla moved there with her mother & some of her siblings. She eventually shared a house with her brother Caesar and sister Duruxa. She never married. As she aged, Cill's eyesight failed and unlike in Deerfield, townspeople in Sunderland cared for her and provided meals and clothing. By 1838, the town was providing for her. Drucilla Prince died a pauper in Sunderland on November 21, 1854, at the age of 94 years. Townspeople provided a shroud and coffin, and they layed her out and buried her. She was the last of the Prince children to die. Drucilla was remembered for her wit and her skill for telling stories, much like her mother.