The Florida Highwaymen have cemented their place in Florida art history, leaving a vibrant, lasting legacy along the Treasure Coast. Originating primarily from Gifford, located just adjacent to Vero Beach, and neighboring Fort Pierce, this historic group of 26 Black artists profoundly transformed the local art scene starting in the 1950s.
Driven by the realities of segregation, a restricted art market, and the necessity to earn a living, the Highwaymen pioneered a unique, entrepreneurial approach to selling their artwork directly to the public.
Rather than relying on traditional galleries—which were largely inaccessible to them at the time—these artists sold their stunning Florida landscape paintings from the trunks of their cars, along highways, and door-to-door. Originally selling for as little as $25, these highly sought-after pieces can now command tens of thousands of dollars from collectors today.
The moniker “Florida Highwaymen” was not actually coined until 1995 by art historian Jim Fitch. Today, researchers like retired psychologist James “Jim” Oelschlager continue to document their incredible lives through historical archives, highlighting how their traveling sales method was born out of both necessity and profound innovation.
It is fascinating to observe the regional stylistic differences that emerged within the group:
- The Gifford Artists: Painters tied to the Gifford area became known for a slower, highly detailed, and realistic style. Harold Newton, who returned to Gifford in 1953, studied under renowned Fort Pierce landscape painter A.E. “Bean” Backus. Newton is credited with pioneering the traveling sales method by 1954 and innovating the distinctive carved-in signature technique utilized on wet Upson board.
- The Fort Pierce Artists: Conversely, many Fort Pierce artists adopted a quicker, “fast painting” method. Alfred Hair, who also studied with Backus after an introduction by Lincoln Park Academy art teacher Zanobia Jefferson, developed an assembly-line approach to painting that heavily influenced the Fort Pierce contingent.
Out of the original 26 members, Mary Ann Carroll was the sole female artist. As of May 2026, only two original members remain living: Curtis Arnett and Sam Newton.
The impact of the Florida Highwaymen continues to be celebrated across Indian River County, St. Lucie County, and the broader nation. Their artwork provides an enduring cultural footprint that is preserved through several major initiatives:
- The Fort Pierce Museum: The City of Fort Pierce Highwaymen Museum officially opened on February 20 in the Jackie L. Canyon Sr. Building at 1234 Avenue D. Operating on Saturdays and Sundays from noon to 4 p.m., it is billed as the only museum in the world dedicated strictly to the group’s legacy.
- Annual Heritage Festival: The museum’s grand opening coincided with the ninth annual Highwaymen Heritage Trail Art Show and Festival at Moore’s Creek Linear Park, an event that celebrates original members, second-generation artists, and local regional creators.
- National Acclaim: Inducted into the Florida Artists Hall of Fame in 2004, their work has been displayed in Tallahassee’s Museum of Florida History and the Smithsonian’s National Museum of African American History and Culture, which opened with 18 Highwaymen paintings in 2016. Furthermore, in 2011, Mary Ann Carroll presented one of her paintings to Michelle Obama in Washington, D.C.
- Media and Heritage Awards: The group received the Florida Folk Heritage Award in 2020. Most recently, the biographical film Legends of the Highway was released on streaming and DVD in October 2025, featuring actor Kelvin Hair portraying his grandfather, Alfred Hair.
For residents of Vero Beach and the Treasure Coast, the story of the Florida Highwaymen is an inspiring testament to local resilience, artistic brilliance, and the enduring beauty of Florida’s natural landscapes.
