The Florida Highwaymen artists represent a significant movement in American art history, known for their vibrant depictions of Florida’s landscapes and their unique entrepreneurial approach. The Highwaymen emerged in the late 1950s, primarily in the Fort Pierce and Gifford areas, and their influence continues to shape the appreciation of outsider and folk art across the state and beyond.
Florida Highwaymen Artists: Origins and History
The Florida Highwaymen artists began their work during an era marked by racial segregation and limited economic opportunity for African Americans in Florida. According to art historians, the group consisted of 26 African American artists, mostly men, who developed a distinctive style and business model out of necessity.
Rather than relying on traditional galleries, which often excluded Black artists, the Highwaymen sold their paintings directly to customers. They used the trunks of their cars and local businesses along highways to reach buyers throughout the region. This independent strategy gave rise to the name “Highwaymen.”
Distinctive Style and Artistic Techniques
The art produced by the Florida Highwaymen is characterized by bold colors, expressive brushwork, and quick production methods. Many works were created on inexpensive construction materials, such as Upson board, due to limited resources.
Common subjects include palm trees, sunsets, swamps, and beaches, capturing the natural beauty of Florida’s changing landscape. The Highwaymen’s style is often classified as “Outsider Art” or “Folk Art,” reflecting both their self-taught backgrounds and their outsider status within the mainstream art world.
Enduring Impact and Recognition of the Florida Highwaymen
The Florida Highwaymen artists produced an estimated 200,000 paintings over several decades. Their work is now recognized for its cultural and historical significance, documenting a rapidly evolving Florida and highlighting African American contributions to the arts.
Major institutions, including the Smithsonian and the Florida Capitol, feature Highwaymen paintings in their permanent collections. In 2004, the group was inducted into the Florida Artists Hall of Fame, further cementing their legacy.
Highwaymen Art in Museums and Exhibitions
Recent years have seen renewed interest in Highwaymen art. Notable exhibitions, such as “Making Their Way: The Florida Highwaymen Painters” at the Addison Gallery of American Art in fall 2025, introduce new audiences to their unique vision and the historical context of their work.
Books, documentaries, and museum displays continue to explore the Highwaymen’s story, emphasizing their resilience and the lasting appeal of their art.
Current Highwaymen Artists and Continuing Legacy
Following the death of Al Black in 2025, only four original Florida Highwaymen artists remain: Roy McLendon Sr., Isaac Knight, Charles Walker, and one other member. These artists continue to produce new works and participate in exhibitions, preserving the group’s legacy for future generations.
Second-generation Highwaymen, including family members and close associates, have also embraced the tradition. Their efforts have expanded the movement’s reach and ensured that the Highwaymen’s influence endures.
Entrepreneurial Spirit and Social Impact
Experts highlight the Highwaymen’s innovative approach to business and art. By bypassing mainstream galleries, they developed a direct-to-customer model that allowed them to overcome economic and social barriers.
The group’s story is often cited as a testament to the power of entrepreneurship and creativity in the face of adversity. Their paintings serve as a record of African American cultural history in the American South, as well as a celebration of Florida’s natural environment.
Frequently Asked Questions About Florida Highwaymen Artists
What are Florida Highwaymen artists known for?
Florida Highwaymen artists are known for their vivid landscape paintings of Florida, created using bold colors and rapid techniques. They sold their art directly to customers, often from their cars, due to exclusion from mainstream galleries.
How many original Highwaymen artists are still alive?
As of 2025, only four original Florida Highwaymen artists remain alive. They continue to paint and participate in art exhibitions.
Are Florida Highwaymen paintings valuable?
Yes, Florida Highwaymen paintings are highly sought after by collectors and are displayed in major museums. Their value has increased as their cultural and historical significance has become more widely recognized.
Can you visit Florida Highwaymen art exhibits?
Yes, Highwaymen art is featured in various museums and galleries, including special exhibitions like “Making Their Way: The Florida Highwaymen Painters” in 2025. Permanent collections can be found in institutions such as the Smithsonian and the Florida Capitol.
Where did the Florida Highwaymen artists work and sell their art?
The Highwaymen primarily worked and sold their art in the Fort Pierce and Gifford areas of Florida. They traveled along highways across the region, selling paintings door-to-door and from their vehicles.
