Wine and painting: Florida Highwaymen Poinciana Painting

Join us for a special evening at Cleveland Street Market as we step into a unique piece of Florida’s cultural history. The Florida Highwaymen were a group of African-American artists in the 1950s and 60s who painted vibrant, iconic Florida landscapes—often on the side of the road—and sold them to tourists. Their bold colors and quick brushwork captured the essence of Florida’s natural beauty and became a deeply historic part of the state’s cultural identity.

We’ll be guided by Caroline, an experienced local artist and teacher who has been leading painting classes for more than a decade. Caroline began teaching in 2007 and quickly discovered her passion for helping beginners find their artistic voice. She has taught at the Safety Harbor Museum, Dunedin Hale Senior Center, and other venues, and her workshops—rooted in fun, encouragement, and creativity—make painting approachable for everyone. Caroline will introduce us to the story of the Florida Highwaymen and then guide us through painting our own Poinciana masterpiece.

Note: the cost of $25 includes all the materials for the painting and our teacher, Caroline's time. Food, beer and wine are extra.

📍 Where: Cleveland Street Market, Clearwater, FL
🕕 When: 6:00–9:00 PM (Painting session 7:00–9:00 PM)
🍷 Extras: Food, wine, and beer available on site

Come for the art, stay for the conversation, and leave with a painting you created and a new appreciation for one of Florida’s most remarkable cultural legacies!