Winslow Homer's first and most important patron was Lawson Valentine, a varnish manufacturer, who eventually owned approximately forty works by the artist. The Homers and Valentines had known each other since their childhood in Cambridge, Massachusetts. Homer became closer with the Valentine family as Charles Homer, Winslow's brother, joined Valentine & Company as chief chemist, then chairman for the company.
In 1876, Lawson Valentine acquired a large farm in Mountainville, New York, seven miles from West Point. Valentine bought horses, Jersey cows and Southdown sheep for the working farm. Homer visited the property, named Houghton Farm after Mrs. Valentine's family name, in 1876 and returned in 1878. Homer spent the entire summer and fall of 1878 painting approximately fifty watercolors and a large number of drawings and studies.
At Houghton Farm, sheep husbandry was an essential part of the working farm and during his stay, Homer produced a great number of watercolors of this bucolic subject. G.W. Sheldon wrote in 1882, "Winslow Homer, indeed, never fully found himself until he found the American Shepherdess." (as quoted in F. Ilchman, Winslow Homer in the 1870s: Selections from the Valentine-Pulsifer Collection, Hanover, 1990, p. 67) These graceful works of lone shepherdesses, withdrawn and in contemplation were reflections on the way Homer was feeling at the time.
In the February 16, 1879 New York Sun, was written, "It is rather surprising that an American artist should come home to his studio...with a portfolio full of "little Bopeeps," as Mr. Homer has done. He found a region, apparently, where there were shepherdesses not only as real as sheep and crooks could make them, but possessed of all the daintiness of the true and original porcelain...To Mr. Homer belongs the distinction of having discovered the American shepherdess and introduced her to the public in studies that are more essentially and distinctively pastoral than any American artist has yet attempted." (as quoted in N. Cikovsky, Jr. and F. Kelly, Winslow Homer, New Haven, 1995 p. 163)
These idyllic scenes were also seen in political terms as a symbol of American freedom and moral virtue of rural life. Written in New York Evening Post, March 3, 1880, "Here are the American shepherdesses which only Mr. Homer paints --self-possessed, serious, independent; not French peasants who till the soil; not Swiss slaves who watch cows, knitting stockings meanwhile with eyes downcast; not German frauen...but free-born American women on free-soil farms." (Winslow Homer, p. 164)
A Shady Spot is a lovely example of Homer's American shepherdess watercolors and is similar to the Houghton Farm watercolors Susan N. Carter noted in The Art Journal from 1879, "We have rarely seen anything more pure and gentle than the little American girl...half hidden away in dark shade of the trees, with her sheep at her side. The picture, too, is delightful in chiaro-oscuro. But it takes an artist as well informed as Mr. Homer to dare to contrast such a dark, clear shadow with the brilliant dash of sunshine which isolates the little shepherdess from the spectator, and throws her woody retreat into a poetical remoteness." (as quoted in N. Cikovsky, Jr. and F. Kelly, Winslow Homer, New Haven, 1995 p. 162) The shepherdess in A Shady Spot stands under a large, leafy tree taking a rest from the brilliant sun. Dappled light hits her skirt as she stares off in thought. Homer has painted the chiaroscuro S. Carter discussed, with the contrast between the dark shade the shepherdess stands in and the bright sun that radiates off the grass beyond the tree. Lost in reverie, Homer's lone sheperdess symbolizes a vanishing past and a more virtuous agrarian present.
Frederick Ilchman concludes, "Homer's Houghton Farm images of shepherdesses illustrate, more strongly than any other subject matter he chose to represent, the nostalgia then present in his work. Themes of childhood and rural life, found throughout Homer's oeuvre, were especially abundant in the 1870s. In the aftermath of the Civil War, and with the coming of the 1876 Centennial Exhibition, artists like Homer turned to sentimental subjects hoping to find a 'sense of permanence and continuity within the disjunction of modern life.'" (Winslow Homer in the 1870s: Selections from the Valentine-Pulsifer Collection, pp. 70-71)