Stuart left Washington for Boston at the invitation of Massachusetts senator Jonathan Mason, who promised to introduce him to friends, relatives, and associates there. He found patronage among a range of the city’s residents, including Paul Revere and mayor Josiah Quincy as well as younger sitters like Lydia Smith, whose complex portrait reveals her to be an accomplished young lady with both musical and artistic talents. At first Stuart may have considered Boston a temporary stop––he reported to a friend that the city was too cold for him––but he spent his last twenty-three years there, in demand not only as a portraitist but also as a guest at dinners and other social events. He was visited by many younger artists who sought advice or simply wished to pay their respects.
Stuart's strengths as an artist did not diminish as he grew older, even though his tremulous hand occasionally handled paint in a less exacting way. His late, life portrait of John Adams is a moving image of the frailty and dignity of old age. The ninety-year-old former president clasps his cane with bony fingers rendered in strong highlights and thin areas of shadow. Although his body is aged, Adams' alertness shines through in his blue eyes, which return the viewer’s gaze clearly and directly. The portrait is a tribute both to the elder statesman’s enduring personality and to Stuart's unflagging abilities in his own final years.