Pictured: Backwater Sunset" by Livingston Roberts, painted on Upson Board, 24" x 36". Photo courtesy of The City of Sarasota.

Inside Sarasota’s City Hall, history awaits. Earlier this month, a collection of 26 paintings from the famed Florida Highwaymen went on display in the Cultural Heritage Exhibit in the City Hall atrium. The exhibit, which is free and open to the public, is on loan from Roger Lightle, a Highwaymen art collector and owner of the Highwaymen Art Specialists, Inc and will be on view for the next six months.

The paintings of the Florida Highwaymen, which range in date from the early 1960s to the 1980s are unmistakably beautiful. Sharp brush strokes of oil on canvas bring the landscapes of old Florida to life, the subject matter exploding with color and vibrancy, giving way to paintings that are somehow haunting and nostalgic all at once. But it is the story behind the paintings that makes this collection all the more special. The Highwaymen, which consisted of 25 men and one woman, were a group of Black landscape painters that arose out of rural Florida in the 1950s. Because of the color of their skin however, they weren’t afforded the opportunities that white artists in Florida were at the time–the Highwaymen were forced to sell their paintings out of the trunks of their cars, oftentimes on the side of highways. So came the name, the Highwaymen.

“The Florida Highwaymen were really not the Highwaymen at the beginning of their career. They were just 26 Black artists who were really struggling to gain relevance in the visual arts because of the Jim Crow era laws and social structure,” says Mary Davis Wallace, the Public Art Manager for the city of Sarasota. “They weren’t able to obtain any representation in the typical fine art galleries in Florida. Instead of abandoning what they loved, they found another way to sustain themselves financially by taking it to the streets.”

For Wallace and the rest of the team at City Hall, this exhibit is so much more than just the chance to showcase some beautiful landscape paintings. It’s an opportunity to tell the story, the whole story, of what Florida used to be like through the efforts of this seminal group of painters. “When you look at these paintings, knowing their story, you’re also seeing a struggle. This isn’t just a peaceful landscape–there is an intensity in these landscape paintings because these are paintings that are trying to survive,” says Wallace. “It’s a record of a time that needs to be processed with stories that need to be told.”

Monday through Friday, 8 am to 5 pm, Lectures with Roger Lightle will occur on Tuesday, February 13, Sarasota City Hall, 1565 1st St, Sarasota.

Pictured: Backwater Sunset" by Livingston Roberts, painted on Upson Board, 24" x 36". Photo courtesy of The City of Sarasota.

To learn more, visit