The Highwaymen: Florida’s Visionary Painters of the Landscape

In the 1950s, a group of young African American artists in Florida began painting the state’s lush landscapes; royal poinciana trees in bloom, dramatic coastal skies, glassy wetlands, and golden sunsets. Collectively known as The Highwaymen, these painters created a body of work that is now celebrated as one of the most significant movements in American regional art.
At the time, opportunities for Black artists were limited. Shut out of galleries and mainstream art markets, the Highwaymen forged their own path. They painted quickly, often completing works in a single sitting and sold them along Florida’s highways, outside businesses, and door-to-door. Their bold colors and expressive brushwork captured the state’s natural beauty in a way that appealed to tourists, locals, and businesses alike.
Though initially dismissed as “roadside art,” their paintings have since gained recognition for both their artistic merit and their cultural significance. In 2004, the 26 original Highwaymen were inducted into the Florida Artists Hall of Fame, and today their works are highly sought after by collectors and museums.

Featured Works in the Upcoming Auction
The upcoming Circle Auction sale on Bidsquare.com The Highwaymen: African American Visions of the Florida Landscape features an extraordinary selection of paintings by some of the group’s most important artists.

Featured Lots:

Harold Newton, Summerlin Dock Evening
Newton was one of the founding Highwaymen and widely regarded as one of its most technically accomplished painters. Known for his luminous skies and refined brushwork, this twilight dock scene shows his gift for atmosphere and detail.

Harold Newton (Florida, 1934-1994)
Summerlin Dock, Evening
Oil on board
20" x 16"
Estimate: $4,000 - $8,000

Harold Newton, Night Palms
Another masterful work by Newton, capturing a moonlit Florida night with a dramatic play of shadow and light.

Harold Newton (Florida, 1934-1994)
Night Palms
Oil on Upson board
32" x 24"
Estimate: $3,000 - $5,000

Roy McLendon, Sunset
McLendon, another original Highwayman, is celebrated for his radiant use of color and expressive brushwork. His Sunset glows with warm tones that reflect his deep connection to Florida’s ever-changing skies.

Roy (R.A.) McLendon (Florida, 1932-2024)
Sunset
Oil on Upson board
22" x 16"
Estimate: $2,000 - $4,000

Sam Newton, Moonlit Palm, St. Lucie River
The younger brother of Harold Newton, Sam continued the family’s artistic legacy. His moonlit river view evokes serenity and strength, hallmarks of his distinctive style.

Sam Newton (Florida, b. 1948)
Moonlit Palm, St. Lucie River
Oil on Upson board
24" x 18"
Estimate: $1,500 - $2,500

Alfred Hair, Ocean Palms 
Alfred Hair is often called the driving force behind the Highwaymen movement. Known for his speed and bold, sweeping brushstrokes, Hair painted with extraordinary energy. 

Alfred Hair (Florida, 1941-1970)
Ocean Palms
Oil on Upson board
24" x 48"
Estimate: $2,000 - $4,000

Auction Details
This special sale offers collectors the rare opportunity to acquire works from the artists who transformed Florida’s landscape into an enduring cultural legacy.

Auction Date: August 30, 2025 at 9AM CT
Explore the full catalog and register to bid on Bidsquare.com.