Woodward was born in Rockport, Massachusetts, the locale of the artist's first direct inspiration. He was influenced greatly by the natural beauty of the rocky New England coastline. As a result, the greatest portion of his work are marines in the media of painting, etching and illustration.
During his long life, he contributed to many periodicals such as American Artist, Ford Times and Collier's Magazine as well as authoring Adventure in Marine Painting in 1948. He was also an instructor at the Ringling Art School in Sarasota, Florida.
Exhibiting widely and receiving numerous prizes and awards, he showed with many major galleries including the National Academy of Design, the Corcoran Gallery of Art and many others. He was also a member of the prestigious American Watercolor Society.