A free art exhibit showcasing the iconic Florida Highwaymen’s paintings kicked off in January, but today will be refreshed with 20 to 24 new paintings and extended for another six months in the Cultural Heritage Exhibit in downtown Sarasota’s City Hall atrium. 

Along with the refresh, exhibitor and collection owner Roger Lightle will hold a lecture and two education days with local schools in the fall. His lectures at City Hall in February drew more than 350 people. 

The Black landscape artists’ work dates back to the 1950s. The artists came from the agricultural communities of Fort Pierce and Gifford, in southeast Florida, and the group of young painters—which grew to include 25 men and one woman—became known as The Highwaymen.

Barred from showing their art in whites-only galleries due to racist segregation laws, the 26 resourceful artists sold their artwork from the trunks of their cars during the post-World War II economic boom. The artists were in large part self-taught and not traditionally trained in the arts.

Often depicting natural Old Florida landscapes of beaches, birds, poincianas and palm trees, the works came about during the Jim Crow era in the South. At the time, employment for Black residents was most often agricultural field work and factory work. Painting was a daring and novel way to earn a living and pursue a creative career during oppressive times.

“These works captured idyllic, romantic landscapes of old Florida,” says Mary Davis Wallace, public art manager for the City of Sarasota. “We’re honored to partner with Roger Lightle to share the narrative of the Highwaymen and provide access to the public free of charge. Visitors will not only experience these beautiful pieces, but will learn about the Highwaymen’s contribution to the genre of Florida landscape painting.”  

The Highwaymen relied on high-volume production and inexpensive methods, selling each piece for roughly $25. They worked quickly and produced dozens of paintings every day to make ends meet. Their signature quick strokes captured an impressionist style, while an assembly line system allowed multiple paintings of similar scenes with unique details to be worked on simultaneously. The paintings and frames were made from inexpensive construction materials, including fiberboard and crown molding, to cut down on costs, and deep frames made of repurposed molding allowed the paintings to be stacked on top of each other in cars for easy transportation.

From the mid-1950s to 1970, the Highwaymen produced roughly 200,000 works, significantly contributing to the genre of Florida landscape painting. They were inducted into the Florida Artists Hall of Fame in 2004.

The exhibit is on loan from Lightle, a Highwaymen art collector and owner of the Highwaymen Art Specialists, Inc. in Vero Beach, Florida. Since the late 1990s, Lightle has collected roughly 700 Highwaymen paintings, amassing one of the most relevant collections of the genre.

The exhibit is part of the city’s Cultural Heritage Exhibit, which launched in November 2022 with the aim to share the cultural arts history of Sarasota and Florida. Exhibits are on display on a six-month rotation, outside of this one, which is being extended for a second rotation. The exhibit is a collaboration between the city’s public art program and the historic preservation department, in conjunction with community partners.

Admission is free and open to the public Monday to Friday from 8 a.m. to 5 p.m., at Sarasota City Hall, at 1565 First St. For questions, email [email protected].