Rosen settled in New Hope in 1903 after studying at the National Academy of Design and at the New York School of Art under William Merritt Chase and Frank Vincent Dumond. He joined the American Impressionist colony in Bucks County and later became a member of the New Hope Group. Having maintained allegiance to American Impressionism, Rosen began to experiment with modernist elements in 1917. His move to Woodstock in 1918 to teach landscape painting at the Art Students League Summer School only cemented his desire to change his style altogether. He became a permanent resident a year later and settled in Rock City with Eugene Speicher and George Bellows. Rosen taught with Andrew Dasburg and Henry Lee McFee at the Woodstock School of Painting which the group founded in 1922.

Rosen traveled to nearby Kingston and Saugerties, chosing man-made structures such a bridges, mills and industrial sites around the Hudson River and Roundout Creek as subjects for his paintings. Using a limited range of colors, Rosen transformed his subjects into simplified rectangular forms that created a rhythmic composition. At the same time he maintained a narrative of the local environs which was an important theme for his works from the Woodstock period. These elements can be seen in Bridges in Winter, Two Tugs (lot 23) and River Boat (lot 25). During the Depression, Rosen contributed art for public buildings in Kingston and Saugerties and received numerous public commissions from government relief agencies.