Following his seafaring career, Winter enrolled at the National Academy of Design in 1921 and continued his artistic studies in 1925 on a traveling scholarship to Paris and Rome.
He exhibited extensively from the 1920s until the 1950s, consistently earning medals and awards, and became a member of numerous artistic societies, including the National Academy and the American Watercolor Society. During his career, Winter discovered a constant source of inspiration in the remote and rugged scenery of Monhegan Island, a place he continued to visit throughout his lifetime.
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