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Unlike Childe Hassam, whose closely framed studies of picturesque old houses resemble craggy ancestral portraits, Metcalf stood back from his subject and carefully selected architectural and geographic features that projected a pastoral view of old New England. His trademark subjects—church steeples, farms, and small towns nestled in panoramic autumnal landscapes—literally and figuratively "fixed" upper-class anxieties about change and disorder in an era of rapid immigration, industrialization, and urbanization.

Ironically, Metcalf was born in Lowell, Massachusetts, the milltown that became synonymous with modern New England. He apprenticed with the painter George Loring Brown from 1875 to 1876, but soon became interested in spiritualism, rebelled against Browns classical tastes, and moved on to the newly formed Museum School of the Museum of Fine Arts, Boston (1877–78). Metcalf's principle instructors at the MFA were the painter Otto Grundmann and anatomist William Rimmer. Metcalf worked in a toned-down palate, when compared with French impressionists, and created visually and thematically accessible images for his well-to-do patrons. He exhibited frequently, as one of "The Ten" and solo in major New York galleries. Popularity did not provide personal stability, however. Metcalf went through his career as a peripatetic, wandering from one New England watering hole to the next. Thrice divorced and often impecunious, Metcalf painted landscapes that depict a harmony absent from his personal life.

William H. Truettner and Roger B. Stein, editors, with contributions by Dona Brown, Thomas Andrew Denenberg, Judith K. Maxwell, Stephen Nissenbaum, Bruce Robertson, Roger B. Stein, and William H. Truettner Picturing Old New England: Image and Memory (Washington, D.C.; New Haven, Conn; and London: National Museum of American Art with Yale University Press, 1999)