The Highwaymen, often referred to as the Florida Highwaymen, were a group of African American landscape artists who captured the natural beauty of Florida’s landscapes during a time of segregation in the United States. Teaching students about the Highwaymen is essential in understanding not only the history of African American art but also uncovering vital lessons about perseverance, entrepreneurship, and overcoming adversity.

Introducing students to the Highwaymen can be done in various ways, depending on the age group and subjects being taught. Here are some key aspects to cover when teaching students about this exceptional group of artists.

1. Historical Context

Educate your students about the historical context surrounding the emergence of the Highwaymen. It is essential to mention that most of these artists were self-taught, primarily because they had limited access to formal art education due to racial segregation in Florida during the 1950s and 1960s.

Discuss how their artwork served as an escape from harsh living conditions and limited job opportunities for African Americans during those times. Emphasize their resilience as they used available resources – such as upcycling old materials like construction debris and spare wood – to create their masterpieces.

2. Entrepreneurship and Marketing Strategies

Highlight the entrepreneurial spirit of these artists who traveled across Florida selling their artwork directly from their car trunks. Discuss their unique marketing strategies at a time when selling African American art through galleries was unheard of due to racial prejudice.

Teach your students how these artists managed to create a market for themselves by cutting out intermediaries, pricing their work moderately, allowing their pieces to reach a wider audience.

3. Art Techniques and Styles

Showcase examples of Highwaymen artwork featuring beautiful depictions of Florida’s scenic coastal landscapes, tropical forests, swamps, sunsets, and night skies. Discuss their distinctive artistic styles characterized by bold colors, untamed flora, and sweeping vistas. Teach students about art techniques they employed in their vibrant landscape paintings, such as the use of quick brushstrokes, palette knives, and blending colors directly on the canvas.

4. A Lasting Legacy

Finally, discuss the lasting impact of the Highwaymen on art history and African American culture. Emphasize the importance of preserving their work and acknowledging their contribution to the world of art despite significant challenges they faced due to social prejudices.

Invite your students to analyze the influence of their artistic legacy on modern-day artists in the Black community and local Floridian artists who continue to be inspired by their work.