At the beginning of the twentieth century, Maurice Prendergast was the most modern artist in America. The Boston painter was unusually receptive to the art of the Post-Impressionists, whose work he saw in Paris. In Prendergast's art, traditional conceptions of space and naturalistic color gave way to emphasis on the flat surface of the canvas, bold colors, formal simplifications, and decorative outlines. In paintings scenes of outdoor recreation, he expressed an arcadian world of charming, almost childlike innocence.
Prendergast may have exhibited "New England Harbor" at the Art Institute of Chicago in 1919. An early photograph of the picture, however, shows a previous stage in the composition's development. The male figure seated in the foreground is not present in the photograph, nor are most of the patterns of lozenge-shaped dots that adorn the women’s dresses. The picture as we now know it has a distinctive tapestry-like effect, heightened by the dissolution of form into these colorful patterns and by the multiple layers of paint that encrust the surface.