The Florida Highwaymen: 200,000 Paintings Sold from Car Trunks

In the 1950s, a group of young Black artists in Fort Pierce started painting Florida’s sunsets, palm trees, and churning seas. They couldn’t hang their work in galleries, so they loaded wet canvases into their cars and sold them door to door along I-95 and A1A for $25 apiece. Over three decades, they moved an estimated 200,000 paintings.

From Citrus Groves to Canvas

In segregated 1950s Florida, most available work for Black men meant citrus groves, tomato fields, and factory floors. But in 1955, a Lincoln Park Academy art teacher named Zanobia Jefferson introduced her 14-year-old student Alfred Hair to A.E. “Bean” Backus, a prominent white landscape painter in Fort Pierce. Backus took Hair on as a student, teaching him to capture Florida’s light and color. Harold Newton, another young painter, soon followed. Word spread, and eventually 26 artists formed the loose collective now known as the Florida Highwaymen.

$25 Paintings, $50,000 Masterpieces

The Highwaymen painted fast and in volume. Working from memory and imagination in their backyards, they used Upson board (a cheap construction material) instead of canvas and built frames from crown molding. A single artist could produce dozens of paintings in a day. They loaded the still-wet work into their cars, stacking paintings in deep homemade frames, and drove up and down the coast selling to banks, offices, doctors, and anyone who answered the door. The name “Highwaymen” came later, coined by art collector Jim Fitch in 1995. Today, those $25 roadside paintings fetch $5,000 to $50,000 or more at auction.

Where to See Them

The Highwaymen were inducted into the Florida Artists Hall of Fame in 2004, and 18 of their paintings hang in the Smithsonian’s National Museum of African American History and Culture. The A.E. Backus Gallery & Museum in Fort Pierce holds annual Highwaymen exhibitions and is the best place to see the work in context. The Museum of Florida History in Tallahassee owns pieces by 23 of the original 26 artists. Mary Ann Carroll, the only woman in the group, is among several surviving Highwaymen who came out of retirement to meet renewed demand for their vivid, unmistakable Florida scenes.