DAVENPORT – Al Black can remember driving along U.S. 27, to a truck stop where he would park, unload a series of paintings from his car, and then walk around greeting people, seeing if they liked his work.
“When the old Haines City truck stop used to be on (U.S.) 27, I was selling there,” he said. “I would see 10 to 12 paintings a day at that truck stop.”
That was in the 1950s and 1960s, long before the group that Black was a member of had developed a name – the Highwaymen – along with a reputation for being pioneers in the field of art, in particular for their historic renderings of Florida’s natural landscape, before development encroached on it.
“That’s A1A, the Indian River Drive,” Black said as he pointed to his paintings. “That’s Vero Beach. That’s a sunrise inlet scenes. That’s a Poinciana tree.”
Pointing to his work, which was on display at the Davenport Community Center on Saturday, Black said in the days when art museums and businesses didn’t take the Highwaymen and their work seriously, he would go directly to the consumer – with success.
“I used to be the salesman for the whole group back in those days,” he said. “They painted it, and I did the selling.”
On Saturday, the Davenport Historic District hosted a free art show at the community center from 10 a.m. to 4 p.m., featuring the original Highwaymen and other Florida Hall of Fame artists. Known as the Second Annual Original Highwaymen Weekend Extravaganza, it was presented by the city of Davenport’s Florida Heritage Series.
“This is our second annual extravaganza,” said Amy Arrington, coordinator of the event, who said it was put on for the benefit of local residents.
“We’re trying to increase our special events and improve the quality of life for our residents,” she said. “Last year it went really well, and we’re expecting this year to be just as good, if not better. Today is an art show which is free and open to the public.”
It will also become an annual event, Arrington said, always held during the first weekend in March.
The Highwaymen are a group of African American artists who, in the racially segregated era of the 1950s and 1960s, were self-taught painters who were not well known, and found it impossible to interest galleries in displaying and selling their artwork.
Instead, the Florida Highwaymen, a group of 26 landscape artists, sold their art directly to the public rather than through galleries and art agents.
The works of the Highwaymen were rediscovered in the mid-1990s by art historian Jim Fitch, and today are recognized as an important part of American folk history. These landscape artists created a body of work containing more than 200,000 paintings that cut across the many racial and cultural barriers of the era they painted in. Since their work got rediscovered, the Highwaymen have become celebrated for their idyllic landscapes of natural Florida settings.
The 26 Florida Highwaymen were inducted into the Florida Artists Hall of Fame in 2004.

“We painted Florida,” said Charlie Walker, one of the original 26, who was at the Davenport Community Center on Saturday. “They’ve been doing that since the 1950s, painting the Florida scene.”
“They painted the environment they lived in,” added his wife, Gertrude Walker. “They were able to record the times they were in.”
Charlie Walker agreed, saying he always loved Florida’s natural beauty. “You can just look around at my paintings, at the habitat,” he said. “As a kid, I loved animals and birds.”
“His father was a hunter, and his mother was fisherman,” Gertrude Walker added. “He became so much in love with wildlife and the habitat, and you can see that in his work.”
Exhibits like the one in Davenport, she added, help introduce new generations to the Highwaymen’s original work.
“This is our first time here,” she said. “I think the significance of the Highwaymen is the fact that they are self-taught entrepreneurs that made a life for themselves in a very turbulent time in Florida history, and they used their talent to create a unique opportunity for themselves. They were very creative.”
When young people discover their paintings and the scenes of an older Florida that they helped capture on canvas, she added, “They’re usually quite impressed with the quality of the work.”

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