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Who Are The Highwaymen Artists?

In the late 1950’s along the central East coast of Florida a small group of African American artists started a business venture that wasn’t suppose to happen, they painted. The jobs available at the time for these artists was most likely in the orange groves picking fruit or other low paying minimum wage employment. This was the Jim Crow era in the south.

Twenty six artists that were loosely associated and centered in the Vero Beach Ft. Pierce area eventually made up the group. They traveled the roads selling their artwork to business owners, real estate brokers, lawyer’s offices, banks and others along the way. In the mid 1990’s these artists were given the name The Highwaymen, because of their sales method.

The Highwaymen artists created an estimated 200,000 paintings. Many of the paintings were purchased by tourists on their winter vacation, and were taken back to their northern homes. Highwaymen artwork has spread across our country. I even know of one in Hawaii.

The artists captured Florida’s natural beauty that is currently being compromised by development. The back woods scenes, breaking waves, palm lined beaches, and river scenes are just a small part of what they painted. They were successful, with 40+ years of painting for artists in the group. They have had two articles published in the N. Y. Times, NPR broadcast across the country on three separate occasions and in 2004 were inducted into the Florida Artists Hall of Fame. They are in the White House and the Florida Governor’s mansion and countless homes and offices across the country. The popularity and demand for the Highwaymen art is ongoing and success they achieved is part of the American dream.


The Vero Beach Art Museum proudly presents “Along the Road: Paintings of The Highwaymen” art show. Thanks to Roger Lightle, for putting together and presenting art work of the Highwaymen for the town of Vero Beach. Many show up to enjoy the beautiful works of art.


Below are some samples of available Highwaymen art. Click here to view all of our available Highwaymen art.
Come back often as we are always posting new paintings.

24" x 36" on Masonite

24" x 36" on Masonite

L. Roberts
24" x 36" on Upson Board

24" x 36" on Upson Board

24" X 30" ON CANVAS

24" x 30" on canvas

R. A. McLendon