‘A landscape painting transcends any racism:’ Meet the Florida Highwaymen this weekend

The landscape artists will be together for the largest gathering the group has had in Mount Dora

The Florida Highwaymen are known for turning paintings of Florida landscapes quickly and selling them from $5 to $25 in the southern region during the Jim Crow era at offices along highways in the 1950s and 60s.

MOUNT DORA, Fla.The Florida Highwaymen are known for turning paintings of Florida landscapes quickly and selling them from $5 to $25 in the southern region during the Jim Crow era at offices along highways in the 1950s and 60s.

Now their paintings sell for thousands of dollars.

[TRENDING: Study: This Florida theme park is more expensive than Disney World | US gas prices dip just below $4 for first time in 5 months | Enter daily to win a $100 gas card | Become a News 6 Insider (it’s free!)]

This weekend, you can meet the group at the 29th Highwaymen show at the Donnelly Park Building in Mount Dora.

Heron Cay Bed & Breakfast Inn sponsors the event. If you stay there you can also get a chance to eat dinner with the Highwaymen and hear their stories.

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.

They were named the Highwaymen because they couldn’t sell their work in art galleries or museums, so they had to take their business on the road.

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)

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

Al Black was part of the original group, known for being the best salesmen. Sometimes the other artists would even ask him to sell their pieces.

“I would go by each one ‘em’s house every day and I’d get, like, 10 paintings and get about 50 paintings. I’d hit the road with them and most of the time I would sell those paintings. I could sell like 40 to 50 paintings a day back then. I would just take them, put five in each hand and I’d go in different offices,” Black said.

He said he even knows the colors that should be in the painting to make it sell.

“They were looking for the visual colors, like the reds and the oranges. The big motels, doctors and real estate offices we would go into to sell, they would buy a bunch of them. Back then, when I started selling, the lowest was $25 for a big painting. I started raising the price to like $75 to $100. That’s how the prices went up on the paintings. Then, after we went into the Artists Hall of Fame, I could just about ask anything I wanted to get for them, because they were high in demand,” Black said.

Check out the Real Talk, Real Solutions podcast in the media player below:

Kelvin Hair is following along his dad’s footsteps. Alfred Hair died in 1970 at the age of 29.

“These guys did this when they were relatively young. We’re talking about teenagers, in their 20s and stuff like that. These were really a bunch of kids blazing this trail back in the day and none of them thought they were going to get famous. They didn’t do this to be recognized. They were just doing this to make money and to eat and survive,” Hair said.

Florida Highwaymen, Kelvin Hair, is the son of Alfred Hair, who helped establish the artist group (Kelvin Hair)

He talked about what it was like for the group to sell their paintings in the Jim Crow era South.

“A landscape painting transcends any racism. When you look at a nice landscape, a light sunset, it doesn’t matter what race you are, what nationality you are. That just appeals and can speak to anybody,” Hair said.

Black has painted several murals in prisons throughout Florida, including the Central Florida Reception Center in Orlando. He said it makes him feel good to see his paintings go for thousands of dollars now and makes him want to put more into them.

“When I was coming up, they told me I wasn’t ever going to be nothin’. I wanted to make them feel like they were wrong. It’s in your mind what you want to be. You can be anything you want to be, all you got to do is put your mind into it,” Black said.

Florida Highwaymen Kelvin Hair and Al Black teaching a class at the Orlando Museum of Art for the kids of Elevate Orlando (Kelvin Hair)

Hair said he believes his dad would be amazed to see the success of the group.

“My dad opened a door for me. Granted, I had to walk through it, but a lot of people don’t get that door opened for you. I just wish he was still here to see what he’s done because there are some paintings that my dad sold for $35 and they sell now for $35,000. He would be tickled if he was still around.”

This weekend’s event is on Saturday from 11:00 a.m. to 5:00 p.m. You can learn more about it here.

About the Author:

Brooke is a news producer and has been with News 6 since January 2018. She grew up in Coral Springs and graduated from the University of Central Florida in 2015 with a bachelor's degree in broadcast journalism. Before she came back to Central Florida, she worked in Fort Myers.