top of page

The Florida Highwaymen


At my school, there's an art museum open to both students as well as the public. I've been there for a few of my classes, and during one of these visits, an art curator explained the story about the latest exhibition recently added to the gallery, showcasing various paintings of Florida, specifically the beach and coastline. Our class started by observing the many paintings hung on walls spanning multiple rooms before we were asked to spot differences in the painting style. While some of these depictions of the beach varied greatly from the others, many of the painting styles were very similar, using the same sized brushes, similar methods of drawing the waves in the sea, and even similar arrangements of the landscape itself, usually with a large palm tree on the left, with the sea in the distance. After a few minutes of these discussions, the museum employee then gave the class the full story behind the exhibition.  These paintings were made by 26 self taught African Americans, 25 men and 1 woman, often called the Highwaymen, with the purpose of creating and selling as many of them as possible. I was astonished to hear that some of these artists were able to create up to 17 paintings a day, yet were still creating such a realistic feel with the brushstrokes. Most of these paintings were then sold along the highways of Florida or sold door to door to doctors offices, banks, or anywhere they could. The appeal of these artworks was their cheap price, often averaging around 25 dollars, letting the middle and middle upper class purchase a painting themselves, which oftentimes was, and is still seen as a luxury. This incredible story of the Highwaymen encouraged me to come back to the museum on my own terms on multiple occasions to observe the many paintings I didn't have to look closely at during my class visit. One of these times I came with a friend, and we had a fun time finding differences in paintings and guessing which two were painted by the same artist and which were painted by different ones. Despite this backstory of the Highwaymen being told to me many months ago during the fall season, the story has stuck with me all this time. The idea of these artists forging a profitable career for themselves, despite living in the heavily segregated Jim Crow era, and additionally creating around 200,000 of these lifelike images seems so incredible, and with the value of these paintings skyrocketing many years after they were created, I felt lucky to be able to see so many of them in person. 

bottom of page