April 11 – May 16, 2026

Our annual Highwaymen Kids exhibition presents vivid Florida landscapes painted by middle school students from the Orange County Public School’s Academic Center for Excellence, College Park Middle School, Glenridge Middle School, and Howard Middle School Academy of Arts.

Each year, between 300 and 500 young artists participate in our Highwaymen Kids competition. Their inspiration comes from the paintings of the Florida Highwaymen, the name given in recent decades to a group of Black artists who took to Florida’s roads in the 1950s and ’60s to market their art. Highwaymen landscapes offer a nostalgic reflection of the state’s natural beauty but also reflect the era of strict segregation, when Black Floridians faced limited job opportunities. The original group – 25 men and one woman – sold their paintings as alternative work to manual labor and asserted economic independence through their art.

On display from April 11 through May 16 on the second floor of the museum, the exhibition offers visitors to the History Center an opportunity to view and appreciate artwork by our local youth that highlights the beauty of Florida through their eyes.