In the l960s, a group of African-Americans taught themselves to paint colorful Florida landscapes in order to escape the hard labor of citrus groves and packinghouses in a segregated south. They painted on upsom board, made frames out of scrap wood and sold their creations out of their cars to motels, doctor's offices, and on the roadside. They painted quickly, creating a distinctive colorful style that captured the mood of an undeveloped Florida – stormy clouds, windy waves, quiet marshes, flowering trees, palms framing a deserted beach.

Based in Ft. Pierce, these artists rode up and down central Florida’s highways selling their paintings for $10 to $45 in the 1960s. Eventually known as the Highwaymen, this group of approximately 25 artists produced up to 200,000 works, creating the beginnings of a regional Florida art tradition. Collectors in the l990s rediscovered Highwaymen art in flea markets and antique shops; today collectors pay up to $10,000 to art dealers for the paintings.

Although in the beginning these artists painted to escape poverty, thirty years later Mary Ann Carroll, the only female Highwaymen, concludes, "if I never sold another one, I'd still paint. I get joy from it." From their unorthodox beginnings, the Highwaymen are now an integral part of Florida's art history.