The Treasure Coast is home to a rich, vibrant history, but few stories are as deeply woven into the cultural fabric of Vero Beach, Gifford, and Fort Pierce as that of the Florida Highwaymen. Emerging in the 1950s, this legendary group of 26 Black artists transformed the Sunshine State’s art landscape, turning a roadside hustle into the last great American art movement of the 20th century.
The Origins of a Treasure Coast Legacy
Faced with the systemic racism of the Jim Crow era and a lack of access to traditional art galleries, these enterprising artists took their work directly to the people. Selling vivid, sweeping Florida landscapes from the trunks of their cars for as little as $25, their entrepreneurial spirit birthed an aesthetic that is now treasured by art historians and collectors worldwide. Today, those same paintings command tens of thousands of dollars.
The artistic roots of the Highwaymen run incredibly deep in the Indian River County area. All eight of the Highwaymen who grew up or developed their skills in Gifford trace their inspiration back to Harold Newton. Newton, who pioneered the traveling sales method, began honing his craft under the tutelage of A.E. Bean Backus, a prominent white landscape painter from Fort Pierce.
Interestingly, the local geography influenced the artwork itself. The Gifford-based artists became known for a slower, highly detailed, and realistic approach to capturing the natural beauty of the region. In contrast, the Fort Pierce painters, led by the charismatic Alfred Hair, often utilized a fast-paced, assembly-line style. Hair’s method allowed artists to quickly paint foregrounds and skies before filling in the iconic Florida trees and grasses.
The movement faced a devastating blow on August 9, 1970, when Alfred Hair was tragically shot and killed at the age of 29 during an altercation at a Fort Pierce bar. Following his death, the prolific output of the Highwaymen began to slow.
Modern Recognition and Preservation
Though the original movement stalled, the recognition of the Highwaymen has only grown exponentially. Officially dubbed the Florida Highwaymen by an art historian in 1995, the group’s enduring legacy includes several major cultural milestones:
- Collective induction into the Florida Artists Hall of Fame in 2004.
- The presentation of a painting by Mary Ann Carroll—the group’s sole female artist—to First Lady Michelle Obama in 2011.
- The inclusion of 18 original paintings at the Smithsonian’s National Museum of African American History and Culture.
- The October 2025 release of the feature film, Legends of the Highway.
February 2026 marked a monumental milestone for the Treasure Coast with the opening of the City of Fort Pierce Highwaymen Museum. Located in the Jackie L. Canyon Sr. Building on Avenue D, it stands as the only museum in the world exclusively dedicated to their legacy. The opening coincided with the ninth annual Highwaymen Heritage Trail Art Show and Festival, celebrating both original and second-generation artists.
Additionally, beautiful new mosaic grave caps created by local artist Anita Prentice were recently unveiled at the historic Black Pine Grove Cemetery in Fort Pierce, honoring legends like Albert Black, Rodney Demps, and Mary Ann Carroll.
With only two of the original 26 artists—Curtis Arnett and Sam Newton—still living as of mid-2026, preserving their history is more vital than ever. Through ongoing local festivals, dedicated museums, and passionate historians, the vibrant legacy of the Florida Highwaymen will continue to inspire the Treasure Coast for generations to come.
