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Here’s how the Florida Highwaymen made an impact in Central Florida

The group of 26 Black artists were based in Fort Pierce, but were often seen selling paintings in Brevard County

Attendees of the Orange County Regional History Center’s Florida Highwaymen Meet and Greet event on December 12, 2015, admire the paintings of the late Highwayman artist James Gibson. (Orange County Regional History Center)

BREVARD COUNTY, Fla. – If you’ve spotted a painting of a Florida landscape in a friend or family member’s living room, it could be from one of the Florida Highwaymen.

It all started when A.E. Backus, who was white, met two young Black men with an interest in painting in the 1950s. He taught Harold Newton and Alfred Hair how to create landscapes on a canvas, and then turn out the paintings quickly.

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The group came to be made up of 26 artists who were eventually recognized in the Florida Artists Hall of Fame in 2004.

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“Backus welcomed everyone into his home, regardless of color, and gave lessons and encouraged artists like Alfred Hair and Harold Newton. Many budding artist found their way to his home and the area became a hub for their art,” said Michael Boonstra, an archivist with Brevard County Historical Commission.

He said they either came from or had some sort of connection to the Fort Pierce area, but traveled for work. They began setting up stands along U.S. 1 or would visit offices to try to sell their paintings as decorations for offices.

A guest at a Florida Highwaymen Meet and Greet event at the Orange County Regional History Center on December 9, 2018, makes a purchase from a representative of Highwayman Robert L. Lewis. (Orange County Regional History Center)

“Their routes included stops along US 1 in Brevard County. The paintings went for $5 to $25 dollars. They often encountered racism with people in the offices yelling at them to get out and adding a racial term,” said Jim Clark, a UCF History professor.

Historians say there could be several reasons as to how paintings from the Florida Highwaymen became so popular in Brevard County.

“The growth of the Highwaymen also coincided with the huge population boom in Brevard County that occurred with the birth of the space program starting in the 1950s. Thousands of people were moving to the area and construction of new homes and businesses was at an all-time high. Most of the new residents were from out of the state and were fascinated by the area’s tropical scenery, which they saw depicted in the colorful Highwaymen art,” Boonstra said.

He believes once families settled into their new houses, they furnished them with the paintings of Florida’s landscapes to represent their new life.

“Since Brevard County was relatively undeveloped at this period there were few major roads, mostly U.S. 1 and A1A, and traffic was a nightmare. People going to and from their jobs at the Space Center and to Patrick (Air Force Base) often spent hours in their cars in traffic jams. This of course provided the perfect audience for the Highwaymen to sell their paintings to. It was a win-win for everyone involved,” Boonstra said.

It’s important to note how the paintings from the group of artists also captures history.

Florida Highwayman Roy McClendon painting at a Florida Highwaymen Meet and Greet on December 9, 2018. (Orange County Regional History Center)

Their work documents buildings that are no longer in existence, like the Hubbs Inn at Cocoa, which was a popular restaurant located on piers over the Indian River.

“Even the scenery that they recorded has changed much over the years as swamps have been drained and built on and the citrus groves depicted are now practically non-existent. They provide a snapshot in time that is important to our history,” Boonstra said.

Even though the Highwaymen started off in the 1950s, they attracted more attention in the 1990s. They began to have shows around the state and were in demand.

“When I first met James Gibson around 2001, he was still selling paintings out of the large trunk of an old Oldsmobile. The last time I saw him about 20 years later he was having a show in Mount Dora and driving a new Cadillac Escalade,” Clark said.

The Highwaymen have had several events at the Orange County Regional History Center.

In 2020, the Orlando Museum of Art held a major show of their work.

Mary Ann Carroll was the only woman among the group of artists, and one of her paintings was given to former first lady Michelle Obama.

Now when you search for Highwaymen paintings online, they’re priced at thousands of dollars.


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