Born and raised in Danville, Illinois, Wood 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, Carl Woolsey. Their father successfully promoted his sons’ paintings, and they won awards in New York and Indiana. Economics later took the family back to Indianapolis. Wood W. Woolsey also lived in Connecticut and Pennsylvania.