In the racially segregated 1950s, a group of twenty-six African American artists from Fort Pierce, Florida, defied the economic limitations of the Jim Crow South by forging a unique path in the art world. Known today as the Florida Highwaymen, these entrepreneurs—including founding figures Alfred Hair and Harold Newton, and the sole female member Mary Ann Carroll—bypassed exclusionary white-only galleries to sell their work directly to the public. Painting vibrant, idealized Florida landscapes on inexpensive Upson board with crown molding frames, they traveled the state's roadways selling their art from the trunks of their cars to banks, motels, and individuals.

Their unique "fast painting" technique, often utilizing palette knives and bold colors, allowed them to produce thousands of works featuring iconic Royal Poinciana trees, dramatic "fire skies," and serene backcountries. While originally sold for roughly $25 to $35, these paintings have since gained significant historical acclaim, leading to the group's induction into the Florida Artists Hall of Fame in 2004.

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