The Highwaymen may be complete unknowns to you. I know they were to me. My youngest daughter brought home a painting she made in school with a little note attached that said “To further their study of Florida, the first graders will learn about a group of Floridian artists, known as the Highwaymen.” I had never heard of the Highwaymen before and so I asked my daughter, who casually replied “they were group of black artists who painted pictures of Florida and sold them along the highways.”

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Fast forward to a few weeks ago, and I discovered that our local history museum was having a “meet and greet” with some of the Highwaymen. Needless to say, I was intrigued. So I did a little homework of my own to discover who the Highwaymen are. 

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1955 in the United States was not a great time to be a black person. Life was even harder if you were south of the Mason Dixon line. In Florida, the governor at the time was a member of the Klu Klux Kan, and so was the chief of police.  Many blacks living in Florida at the time worked in the orange groves – difficult work with low wages. But a brilliantly talented group of 26 men and one woman began painting. They painted with oil on cheap Upson board (similar to modern day drywall). They painted in their garages on the weekends. And because they were black, they couldn’t sell their paintings in any gallery, so instead they would sell them from the trunks of their cars as they drove along Florida’s highways – thus the term “Highwaymen.” Often they sold their works for as little as $25.

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Today, the artwork of the Highwaymen is honored and valued by art lovers worldwide. They were rediscovered by the art world in 1995 when a gallery owner, Jim Fitch, wrote an article for an art journal in which he described their work.  All 26 original Highwaymen were inducted into the Florida Artist’s Hall of Fame in 2004.

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It was a great delight to meet some of the original Highwaymen. My daughter was particularly excited to meet the one and only Highwaywoman, Mary Ann Carroll. All the artists were so gracious in sharing their stories and telling us about their artwork. They drew their inspiration from the Florida landscape all around them  – from cypress swamps to sandy beaches, from the brilliant colors of the jacaranda, poinciana and tabebuia trees to the soft colors of dawn and dusk. Their paintings are a feast for the eyes, their story is a feast for the soul.

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If you’re interested in learning more about the Florida Highwaymen, PBS has done an excellent documentary on them. You can also view their paintings online.

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And if you ever have the opportunity to meet a Highwayman, you won’t be disappointed, and you might just find yourself coming home with a print or two of their enchanting work. 



Michael Lee · September 17, 2018 at 12:52 pm

I find the history of the Florida Highwaymen very interesting. That they followed their dreams even when they weren’t allowed to sell their work in the galleries is awesome to me. I’ve always dreamed to get a pilot’s license, reading this story encourages me to follow my dream and get the pilot’s license.

    Michelle · September 17, 2018 at 1:18 pm

    I’m so glad you were encouraged, Michael! It was so inspiring to meet them. Happy flying!

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