In 1920, at the invitation of Eugene Speicher, George Bellows spent his frst summer in Woodstock. Bellows belonged to the Ashcan School, a loosely associated group of early 20th-century artists working in New York City who favored urban subjects, often gritty in nature. They painted in a realist style that was in contrast to the prevailing and popular academic approaches. Both Speicher and Bellows had studied with its leader, Robert Henri, in New York.

Bellows became in many respects the backbone of Arthur Anderson’s collection and is richly represented by over 150 works, the most of any artist. His circle of artist friends in Woodstock included Speicher and Henri, as well as Leon Kroll, John Carroll, and Charles Rosen, among others.