Starting in the 1950s, a period when America was still deep in the throes of segregation, the Florida Highwaymen defied all odds. A prodigious group of African-American artists who plied their trade painting Florida’s landscapes and sold their work from the trunks of their cars, the Highwaymen discovered success in simplicity. With landscapes that read today like a land remembered, laced with nostalgia, the Highwaymen found a niche to call their own, producing an estimated 200,000 works that have become beloved features of local homes, hotels, restaurants, and museum collections across the region today. Without question, the Florida Highwaymen have become a storied part of Florida’s history.

In this second installation of works on long-term loan from the collection of the Woodsby family, we examine the recurring motifs and techniques that came to define the Highwaymen’s unmistakable style and enduring legacy.