The Florida Highwaymen

By Visit Tallahassee

Collectors of our Scenery and Our History

The vibrant collection of artworks painted by the Florida Highwaymen provide a unique look into Florida’s scenery and history. The Florida Highwaymen were a group of 26 African American painters in the 1950s whose art was sold by going door-to-door to businesses and families across Florida. At the time, black artists were excluded from traditional galleries, leading the Highwaymen to come together to find new ways to make a living. They often sold their work directly from the trunks of their cars- earning them their name. Along the way, they captured Florida’s unique landscape, and today their work stands to memorialize the artistry and Florida’s natural beauty. 

Painting by Roy McLendon

A Piece of Florida’s History

Much of the scenery depicted in these paintings have been lost to years of development. The Florida Highwaymen captured every hue found in Florida’s landscape, from sunsets and Spanish moss. The swaying palm trees, bright flamingos, and vivid sunsets in these paintings share Florida’s hidden beauty. 

landscape painting by mary ann carroll

The Museum of Florida History, featured pieces include the works of Mary Ann Carroll, who famously painted vivid Royal Poinciana trees. R.L. Lewis, one of the more active highwaymen, has been painting since 1967. His work is one of the first ones on display at the museum, featuring Spanish moss, soaring egrets, and flowing rivers. Alfred Hair, considered a founder of the Florida Highwaymen, started painting in his teen years. His artwork at the museum, which is over 50 years old, focuses on the vivid orange colors of a fleeting sunset. In addition to older pieces, the museum also displays some recent works from artists who have been painting landscapes for decades. These artists continue to do what they love, sharing the natural beauty of the Sunshine State. 

 The Highwaymen have since become known nationally for their craftsmanship, with Highwayman Mary Ann Carroll, also known as the First Lady of the Highwaymen, presenting artwork to First Lady Michelle Obama in 2011. Select works are also featured in The National Museum of African American History and Culture. Together, the largely self-taught artists forged a legacy of black artistry. 

See the Florida Highwaymen Exhibit at The Museum of Florida History

The Museum of Florida History features paintings done by all 26 of the Florida Highwaymen. The museum, open seven days a week at varying times, displays exhibits that reflect on the cultural, historical, and natural environment found in Florida. Some of the Florida Highwaymen have passed away since their time of selling artwork on the road, but their art continues to tell their story. Despite racial barriers, these artists produced thousands of paintings that continue to live on in Tallahassee.  


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