Studying the Art of the Florida Highwaymen

I had no idea when a few mom friends and I were sitting by the pool, chatting about life and homeschool plans, that one of them would mention something that would spark so much interest and launch us on a true learning adventure!

It all started with a desire to spend the summer painting en plein air either in the tolerable early mornings or warm evenings of our sun-drenched Florida summers. It was definitely an interest of mine and I was basically inviting the children to join me as I embarked upon a journey to find out something new. Then, in that conversation with a friend, I learned of the Florida Highwaymen, and as I did more research I saw the beautiful opportunity to really dive in and combine it all.

I was so moved by all that I was learning about this group of extraordinary artists, and I decided to write this post in the hopes of either piquing interest about them or helping another family dive into a study as well.  

The Florida Highwaymen (a moniker that didn’t exist until much later) were a group of 26 Black artists (25 men and one woman named Mary Ann Carroll), who during the 1950’s, 60’s, and 70’s, sold their art pieces door-to-door, out of the trunks of their cars, and along the highways of Florida’s Fort Pierce area along the east coast. This Black folk art movement began with two men by the names of Harold Newton and Alfred Hair. 

Hair, at the suggestion of his highschool teacher, Ms. Zanobia Jefferson, met a local artist named A.E. Backus, who taught him and encouraged him to paint landscape art. Harold Newton had also met Backus early on, and was really inspired by him in his own artistic journey. Backus, or “Bean” as he was known, was a progressive of his time. He supported and welcomed artists of different races and from different walks of life into his studio. Backus continued to mentor Alfred Hair, who in turn (along with Harold Newton), inspired other artists, mostly self-taught, to also paint landscape art. The number of Highwaymen soon began to grow.

Set in the era of the Jim Crow South, their story stands out to me for so many reasons. Motivated by the demand for their romantic depictions of undeveloped Florida, they sold their beautiful paintings to tourists and businesses even when galleries were not an option. Uninhibited by traditional rules of painting and color theory, each one of these artists developed their own unique style, but also made the viewer the prime object of the piece by painting what they knew would sell. They worked quickly in an effort to produce more paintings, which was most notably the approach and method of Alfred Hair. 

Their innovative use of materials was far from mainstream (i.e. upson board instead of canvases and carpenter trim instead of frames), and with them, they were able to produce vibrant paintings that really stimulated the imagination. Their obscurity at the time worked to their advantage because they were able to sell their work informally without licenses, as they pleased. By doing something unconventional in their art technique, and in their ways of producing and selling their pieces, this inspirational group of entrepreneurs and artists pushed the boundaries of ingenuity. This wasn’t necessarily their goal at the start, but it certainly was the result, as these 26 artists are recognized today in the Florida Artists Hall of Fame and have artwork included in the collection of the Smithsonian’s National Museum of African American History and Culture.

To begin this study, there were two books that I began to read on my own:

The Journey of the Highwaymen by Catherine Enns (Check the library for this one as the Amazon price seems to have skyrocketed.)

The Highwaymen: Florida’s African American Landscape Painters by Gary Monroe 

My Amazon shop located here has a list of other books on this topic, the names of which I collected and put in one place. However, I only read these two.

*Disclosure: As an Amazon Associate, I earn commissions from qualifying purchases of books and other products mentioned on this blog using these links, at no additional cost to you. I appreciate your support!

Both of these books were written for an adult audience but I quickly realized that it would be easy to share them with my kids, and simply paraphrase important parts that I had selected beforehand. In the end, I used Enns’ book for my own intellectual consumption, as it is slightly more detailed and offers a bit more context than the Monroe book. However, I knew that my children would be excited about seeing the beautiful colored paintings included in both books. There are 204 full color plates in Catherine Enns’ book and 63 full color reproductions of Highwaymen paintings in Gary Monroe’s book. 

We went through Monroe’s book together slowly, with me paraphrasing important parts of one or two pages at a time. We would stop frequently to discuss what we were reading, or to make visual comparisons of the paintings or artists that were mentioned. For this reason, even though we had access to so many of their paintings in the books, I found it helpful to have something to which I could quickly refer, that was digital and in one place. I created this PowerPoint presentation to help us study and compare one painting to another. I cannot promise that the quality of each slide is crystal clear, but like I mentioned before, having some of their work in a digital presentation format proved to be useful. Each of the 26 artists has a slide, and for some artists there are multiple slides simply because I liked the paintings.

Highwaymen Art PowerPoint Presentation: Art of the Florida Highwaymen.pptx

Our process alongside the reading was first, some indoor practice with landscape art techniques, brushwork, and also becoming familiar with what was possible with different types of paint. We used watercolor, acrylic, and tempera paint. I wanted very much to also introduce oil paint, which was the primary medium that Highwaymen artists used, but I decided to leave this for another time. 

Then, we practiced landscape art en plein air (the act of painting outdoors, usually to capture a landscape on site). In fact, we drove to Fort Pierce, home of the Highwaymen, to find inspiration in a new location. We took along our pochade boxes (a 19th century French term that refers to a compact box for carrying the basic necessities of plein air painters) made out of cigar boxes, a simple idea inspired by artist and author Richele Baburina. Each child had their own box and supplies, which they absolutely loved.

In Fort Pierce, we also visited the A.E. Backus Museum and a few other sites along the Highwaymen Heritage Trail. At the museum, we had lots of discussions about what we noticed and observed. There was a short film about the lives of the Highwaymen and a room full of their paintings that are actually a rotating collection. In another room, we viewed Backus’ works and other items on display like his commission book and tools.

At home, we had other landscape art experiences, this time indoors. This was important to me to do with the children because many of the artists actually recalled the scenes they painted from memory and didn’t actually paint en plein air. We used their paintings as a guide for producing our own.

We plan to visit soon the Orange County Regional History Center. This museum houses a smaller collection of Highwaymen art.

Lastly, we included the Highwaymen artists in our Book of Centuries, placing them on a history timeline to understand the circumstances that contributed to their work and lives.

I’m on the lookout for a film slated to come out soon about the Highwaymen, although I haven’t heard any updates about it recently. It is based on a script by Lucien Christian Adderley and Richard “Byrd” Wilson and is being produced by Stars North Films.

Some sites that we used to help us in this journey are listed here. They were great sources of information, especially when I first began to research the Highwaymen. It would be easy to go through the information on these sites with younger children or to let older children browse on their own and discuss with you: 

A.E. Backus Museum and Gallery

Smithsonian’s National Museum of African American History and Culture

Kreol Magazine

Artsy

The Highwaymen (The site that accompanies the Catherine Enns book)

2nd Generation Highwaymen Artist A J Brown


The following sites have video or audio content that I watched or listened to with my kids:

PBS Florida Frontiers Episode on the Highwaymen Artists (26:45 minutes)

Florida Today Video (3:22 minutes), including a link to 47 photos of the Highwaymen

A History of Central Florida Podcast Episode 44: Highwaymen Paintings (12:08 minutes)

NPR News Video about Al Black (6:19 minutes) *There is also audio content above this video (7 minutes).

NPR News Audio Content:

The Highwaymen: Segregation and Speed-Painting in the Sunshine State (10 minutes)

The Landscape Art Legacy of Florida’s Highwaymen (11 minutes)   

*Transcripts are available here. I highly recommend reading them before listening with your children. Doing this helped me to prepare for conversations we had about the role race played in how the Highwaymen were received in their hometown. 

Be sure to preview all audio and video content for sensitive content. You know your children and what they can or can’t handle. 

A final word of advice – it wouldn’t hurt to check your local museums for more places to see art from the Highwaymen (especially if you are in and around Florida). Things become part of temporary collections all the time. In fact, we missed one of these collections at a local museum just last year.

Enjoy! Please do let me know if you’ve found this helpful and if you too are learning about this inspiring bit of history.

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