Born and raised in Danville, Illinois, Carl Woolsey moved to Indianapolis in 1921 and then lived briefly in Long Beach, California. In Indianapolis he saw an exhibition of Taos, New Mexico paintings by Walter Ufer. From 1927 to 1934 he lived in Taos, as did his parents and brothers, including another artist, Wood Woolsey. Their father successfully promoted his sons’ paintings, and they won awards in New York and Indiana, with Carl winning the Hallgarten Prize in 1931 from the National Academy. Carl Woolsey worked with Ufer, using his studio. He also worked for the WPA. Economics later took the family back to Indianapolis. He also lived in Connecticut and Pennsylvania.