Winslow Homer spent the summer of 1878 at Houghton Farm, the country retreat of Lawson Valentine, a business partner of the artist's brother. The idyllic location inspired Homer to create a series of watercolors recording the rural outdoor activities of a cast of youngsters whom he observed as they worked at a variety of chores, watched the flocks, or quietly chatted as they do in this painting, On the Hill.

Homer had been using the watercolor medium regularly since 1873, when he had explored similar subjects of children at play in Gloucester, Massachusetts. His technique involved the masterful pairing of light-filled color with a strong sense of linear design. The positive critical reception of these watercolors encouraged Homer to continue exploring the potential of the medium. Eventually, his mastery of watercolor would bring him lasting fame.