Alfred Hair (the Highwaymen): From Trunk to Trailblazers

A car trunk. A Florida highway. A vibrant and colorful canvas of glowing sunsets and swaying palms. In the 1950s, when art galleries refused to sell paintings by Black artists, the self-taught painters—the Florida Highwaymen—forged their own path by painting swiftly, traveling highways and selling luminous scenes of Florida’s beauty straight from the trunks of their cars, transforming each one into a gallery of their own.

What began with two men—Harold Newton and Alfred Hair—became a movement. Newton, who had originally focused on religious scenes, discovered a new artistic path after meeting Albert E. Backus, a renowned white landscape painter in Fort Pierce, Florida, who mentored young Black artists during segregation. Inspired by Backus’s impressionistic brushstrokes, Newton shifted his focus to painting Florida’s landscapes and began selling them.

Alfred Hair, a charismatic leader, also studied under Backus. Experiencing segregation firsthand at Lincoln Park Academy during the Jim Crow era, he directed his artistic passion and talent toward uniting self-taught young Black artists, sparking the movement and group that became known as the Highwaymen.

The group had 26 members, including Mary Ann Carroll, the only woman among them, who was taught by Harold Newton. Each artist developed a unique style, but they all shared a common mission: to challenge racial barriers by capturing the beauty of Florida through their art.

The legacy of the Highwaymen began to fade after Alfred Hair’s death in 1970. But in the 1990s, journalist Jeff Klinkenberg and historian Jim Fitch helped renew interest in the group and their work. In 2004, all 26 artists were honored with induction into the Florida Artists Hall of Fame. Then in 2016, their cultural impact was further recognized when 18 of their paintings were included in the Smithsonian’s National Museum of African American History and Culture.