After a period of study and travel in Europe on a Guggenheim Fellowship, Gottlieb settled in Woodstock. He worked in Woodstock to help raise funds for artists and was instrumental in establishing the Public Works of Art Project (PWAP) in 1933. His political involvement with labor issues and social reform during this period found direct expression in his art: his subjects, which once revolved around leisurely activities were replaced with images of people at work. In conjunction with this shift in subject matter, Gottleib's stylistic elements permutated into disrupted scale, skewed colors and figures defined as rectangular-like, stout images. Boat in Dry Dock typifies Gottlieb's art at this time, focusing on the labors of the boat men through awkward spatial relationships, altered colors and stocky figures. Gottlieb left Woodstock in 1935 in order to pursue his work and quest for social change in New York City.