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Florida Highwaymen (and woman)



In a local Florida antique mall, my husband and I were struck by a scenic painting that captures the beauty of the Florida coastline. Then we noticed another, and another.

The clerk explained to us that these mid-century paintings were the work of a group of artists known as the Florida Highwaymen.

In Chicago, we've met individual street artists, but this was the first time we'd ever heard about this group of Florida men and women who left behind a legacy of landscapes.

This group of 26 self-taught, African American men (and at least one woman) sold their paintings on the side of highways in Florida in the 1950s. At the time, collectors paid $20 to $40 per painting. Today, some are valued in the thousands of dollars, and the prices continue to rise for the originals.

Not only are the paintings beautiful, but they show their ingenuity, resilience, and remarkable talent.

A few more facts from this helpful website:


  • They painted on Upson board (compressed paper), tree trunk easels and artist's oils.
  • The Highwaymen sold their artwork out of the back trunks of their cars.
  • Painting and selling landscape art was their escape from working in factories and citrus groves.
  • Many of the paintings were sold before the paint had time to dry and were completed in an hour or less.
  • Frames were hand constructed out of crown molding and finished with house paint and gold paint.
  • It is estimated that more than 150 thousand paintings were sold!
  • Today, you can see many of the originals (and imitators) for sale on Ebay.
  • Some of the Highwaymen are still painting today.

For more information and to see a movie trailer, see these helpful websites:






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