After the death of their young daughter in 1841, the Griffith family of northern Maryland commissioned artist Sarah Miriam Peale to paint her portrait. Peale, academically trained and a member of a famous artistic family, was renowned for her paintings of the American elite. Peale’s portrait of Mary “Molly” Griffith—along with a diary kept by the girl’s mother, mourning jewelry, family papers, and a gravesite—makes the Griffith’s grief tangible and highly visible, even today. However, these materials also reveal the experiences of people enslaved by the Griffiths that have been overlooked, including a bondswoman named Caroline whose own story is inextricably intertwined with that of Molly’s. By examining these artifacts collectively and alongside the context of slavery, this article illustrates the complex relationship between labor, loss, and the material culture of mourning.