Goodwin began an artistic career when he was over thirty years old. In 1900, he watched his artist friend Louis Kronberg at work on a pastel and declared, “I think I could do that.” Largely self-taught, he is best known for painting the wharves along Boston Harbor and for his depictions of the city’s streets and gardens.

In 1911, Goodwin exhibited at the Museum of Fine Arts, Boston, alongside many of the top Boston School artists. Soon after, he was accepted into the Guild of Boston Artists, and gained the recognition of such notables as John Singer Sargent and collector John T. Spaulding. Goodwin exhibited locally at the St. Botolph and Union Clubs, Vose Galleries, the Copley Society, the Guild of Boston Artists, and Doll & Richards Gallery. He also traveled back and forth between Boston and New York during the 1910s and 1920s and showed for thirteen years at many important national exhibitions, including the 1915 San Francisco Exposition, the Pennsylvania Academy of the Fine Arts, the Brooklyn Museum, the Carnegie Institute, the Art Institute of Chicago, and the National Academy of Design. Vose Galleries has enjoyed a continued association with Goodwin, featuring him in three one-man shows in 1920, 1985 and 1988.