Many of Lewis Miller's scenes of everyday life offer a glimpse into the lives of the artist and his beloved Virginia relatives while also documenting the dress, architecture, landscaping, and customs of the period. The identity of woman riding side-saddle—"Miss Mary"—is not confirmed, but she may have been Mary M. Ingles, a relative of Miller who lived in Montgomery County, Virginia. Miller created another drawing of Mary Ingles; on it, he wrote that she had a grapevine "close to the house" and "on the sunny side." Perhaps that is the very vine represented in this composition.
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