Celebrating Florida’s Highwaymen, Historic Outsider Artists

Depending on how long you have lived in Florida, you may or may not have heard of the Highwaymen. They are better known today, but not very long ago they were an anonymous group of Florida artists selling original paintings of Florida landscapes from the trunks of their cars.

Though they would not be called the Highwaymen for several decades, these African-American artists created a unique chapter in Florida’s cultural history. From the 1950s into the 1980s, a total of twenty-six individuals from Fort Pierce and nearby areas were creating Florida folk art – and doing it well under the radar of the art world.

The artists featured paintings of familiar Florida scenes – crashing waves on windswept beaches, palm trees bent by the wind, majestic Royal Poinciana trees, moss-draped oak trees, red-orange sunsets, billowing clouds and moonlit rivers.

Their palette included vibrant colors of verdant greens, sunset oranges – and blues and grays that often featured the sun or moon backlighting the scene. The Highwaymen often painted from memory as they captured scenes of the natural Florida they had grown up with, one that was yielding to the development brought on by the state’s mid-Twentieth Century growth.

By necessity, the men (and one woman) painted as an alternative to the backbreaking work of picking and packing Florida citrus – a typical job for African Americans in the 1950’s. Those days were still part of a racially segregated “Jim Crow” South, and painting, then selling their art, gave them an opportunity to succeed in a whole new way.