The sister arts, a concept linking poetry to painting, flourished during Goldsmith’s lifetime. Stemming from the ekphrasis of the ancients, the idea of the sister arts owes to the continental academies of painting during the seicento. Goldsmith became heir to the idea when he was named Professor of Ancient History in the Royal Academy of Painting. Founding president Reynolds exhibited a portrait of Goldsmith at the academy in 1770, the same year that Goldsmith published The Deserted Village. Two years later Reynolds based an allegorical character sketch called Resignation on lines from the poem. From its illustrated title page to its stirring peroration The Deserted Village reflects a continuing appeal to the mind’s eye, an appeal not lost on illustrators from Thomas Bewick and James Gillray to Francis Wheatley and William Hamilton, and many others. Their sketches of Goldsmith’s villagers remain engraved on the imagination of generations. This chapter explores the milieux that link Goldsmith to the visual arts, from his affiliation with the Royal Academy to his cosmopolitan interests.