Captured as he is about to leave for school, young Webster (1834–1872) pauses at the door, cap in hand. With his slightly unruly hair and perhaps a faint smile, he stands in the corner before what appears to be a fireplace mantel, and upon a colorful yet fairly common Venetian carpet. While probably true to life, the size and shape of the boy's head may reflect the nineteenth-century interest in phrenology, a pseudoscientific belief that the shape of the skull could indicate intelligence and character. Here, Webster's broad forehead sculpted in light may have been intended to suggest the boy's astute and moral nature.
The family for whom the portrait was commissioned was one of the earliest to settle in Winchedon, Massachusetts. An 1849 history of the town notes that Seth Tucker, from whom Webster was descended, was one of the original four settlers of Winchesdon village. By 1848 there were "within the limits of the village, 640 inhabitants, 92 dwelling houses, three meeting houses, 1 Academy, 1 school house, 1 large hotel, 9 stores, 1 woolen factory, 1 iron foundry, 1 machine shop, 1 grist mill, 2 saw mills, 1 large bobbin factory, 1 tannery, 1 tub manufactory, 1 pail manufactory, 2 livery stables,... 4 blacksmith shops, and various other shops for manufacturing and mechanical purposes, occupied by carpenters, coopers, wheelwrights, turners, shoemakers, harness-makers, tailors, and other mechanics..." (Ezra Hyde, History of the Town of Winchedon from the Grant of the Township by the Legislature of Massachusetts in 1735 to the Present Time, Worcester, 1849.) In this thriving economy, an artist with Peckham's talents would have readily found a place.