The Florida Highwaymen

About the Highwaymen

In the early 1950’s through the 1980’s a group of twenty-six African-American artists known as the “Florida Highwaymen” used vivid and bright colors to display the beautiful untouched Florida landscape. The Florida Highwaymen painted wind-bent palm trees, serene sunsets, churning oceans and bright red Poinciana trees. They painted from their garages and back yards on inexpensive Upson board and then on the weekends they would travel and sell their Highwaymen paintings to hotels, offices, businesses and individuals who appreciated the artwork for around $25 a piece.

Florida Highwaymen Painting Alfred Hair
Orange Sky, Breaking Surf, 3 Birds by Alfred Hair (1941 – 1970), ca. 1965, Smithsonian Museum

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Highwaymen Paintings for Sale

Collecting Florida Highwaymen art has become an exciting, but often expensive, hobby. The market for an original work of art by a Florida Highwayman artist can easily bring $5,000 to $10,000 or more. Some of the Highwaymen who are still living have resumed painting to meet the continuing demand for their work.

Highwaymen Paintings J Gibson Signed Lower Right Corner 45X25.5” With Frame

Highwaymen Paintings J Gibson Signed Lower Right Corner 45x25.5” With Frame

$3,200.00
highwaymen painting impressive large Livingston Roberts oil on upson board

Highwaymen Painting Impressive Large Livingston Roberts Oil On Upson Board

$5,000.00
🔥 Important Vintage Florida Highwaymen Landscape Oil Painting, 1950s - HUGE

🔥 Important Vintage Florida Highwaymen Landscape Oil Painting, 1950s - Huge

$6,500.00
Highwaymen Painting collectible items Highwaymen memorabilia 7 signatures 2002

Highwaymen Painting Collectible Items Highwaymen Memorabilia 7 Signatures 2002

$2,000.00

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