A major turning point in Winslow Homer’s career occurred when he took up the demanding medium of watercolor for the first time during the summer of 1873 in Gloucester, Massachusetts, where he painted vignettes of young boys and girls at play along the harbor shore. In their relatively tight execution and careful delineation of detail, these works have been called "colored drawings." Executed seven summers later on Ten Point Island, in the middle of Gloucester’s outer harbor, Eastern Point Light belongs to a radically different group of watercolors that shows Homer boldly pushing himself to achieve an unprecedented expressiveness, occasionally verging on abstraction. He began to paint wet on wet, sometimes first soaking his paper in water so that the pigment washes flowed freely, sometimes mixing wet and dry brushwork for certain areas or forms.