On the Trail of the Florida Highwaymen

Last Updated on January 15, 2023

The diminutive man hunched over the canvas with his back to the door is a legend. A Florida Highwaymen. At 90-years-old, R.A. “Roy” McLendon can still be found painting almost every day between 11 AM and 3 PM – or thereabouts – in an utterly non-descript studio/gallery in downtown Vero Beach, FL.

His hand shakes, no longer moving with the swiftness of a young man, but his eyes are “pretty good,” in his own words, particularly after having the cataracts removed.

McLendon represents one of the last living original Florida Highwaymen, an unaffiliated group of 26 landscape painters, all Black, mostly self-taught, who launched their careers in the 1950s and 1960s from Ft. Pierce, one town south of Vero Beach on U.S. Highway 1. That highway – and others like it – gave them their name.

Working in the Jim Crow South, the Florida Highwaymen were shut out of galleries, shows and museums. Instead, they went direct-to-consumer, selling paintings out of the trunks of their cars on roadsides and cold-calling the thousands of new homeowners and businesses moving to Florida during those boom years.  

They worked fast to fill this demand.

Highwaymen sometimes painted more than 20 pictures in a day. The original group is estimated to have produced more than 200,000 artworks during their heyday through the 1970s – any more accurate a figure is impossible to determine. Most of their paintings weren’t dated, titled or formally inventoried in any way. Thousands were unsigned.

The Highwaymen weren’t painting for posterity. They were painting for prosperity.

African Americans during this era in Florida generally faced a lifetime of manual labor to earn a living, often under a blazing sun in the state’s citrus orchards. McClendon did his share of field work as well as a kid.

The Highwaymen painted themselves out of this backbreaking existence by working fast and selling cheap. Theirs was a volume business.

People wouldn’t pay much for artwork from Black painters, but all the new residents needed something to hang over the couch. In the days before Michael’s, Home Goods and mass-produced decorative art, that meant original paintings. In Florida, that meant the Florida Highwaymen. A 48-inch picture of a sunset, perfect to hang over the couch, could be acquired from a Highwayman for $20.

One $20 sale won’t feed a family so the Highwaymen painted and sold as much as they could, using Upson board – a cheap construction material similar to drywall – instead of canvas and framing their pictures with crown molding to keep costs down.

Their remarkable success in doing both created a visual imagery millions still associate with the state: Fruit Loop colored skies, wind-swept beaches, poinciana trees.

By 1980, The Highwaymen’s popularity had waned as the rural, agrarian state gave way to increasingly larger cities and theme parks. A “Miami Vice” image of Florida took over people’s imagination. Residents wanted to look forward, not backward.

Fortunately, their induction into the Florida Artists Hall of Fame in 2004, an ongoing series of books and museum exhibitions in the 2000s, and the acquisition of their work by the Smithsonian’s National Museum of African American History in 2014, has sparked a modern Highwaymen renaissance. They are featured in the Orlando International Airport’s new terminal.

Most of the original members have passed on. Their peak occurred more than half a century ago. Still, communion with the Florida Highwaymen can be found, if you know where to look.

The Legend

Roy McClendon always loved drawing. Growing up as one of 14 kids born to migrant field workers picking beans for a dollar a day the 1930s, that meant using a stick to make pictures in the sand. Today, he paints in an air-conditioned studio inside the Vintage Vero building on 14^th Avenue in downtown Vero Beach.

He still loves it.

Sure, he’ll talk to you about his paintings, but he’d rather brag on the work of his sons – Roy Jr. and Ray – and grandkids. Ray McClendon has a studio and gallery of his own two blocks from his father’s, Florida Highwaymen Landscape Art Gallery, at 1935 14^th Avenue. Visitors can drop in to see him painting most nights – the daytime sunlight being too harsh for him to paint.

The Collector

Roger Lightle owns the preeminent collection of Highwaymen paintings – just ask him. He happily backs up the claim showing guests around his Vero Beach home which doubles as headquarters for Highwaymen Art Specialists, Inc.

500 Highwaymen paintings from his personal collection are joined by a constant stream of original Highwaymen paintings he buys and sells as part of the business. Every wall in the house features a museum-quality Highwaymen painting. He’s turned down six-figure offers for the best.

The best of the best may be Harold Newton’s 1958 painting of a poinciana tree in a green frame which meets guests when they enter the front door. It’s perhaps the best painting of the Highwaymen’s most iconic subject painted by the group’s greatest practitioner at the height of his powers.

Over more than 20 years of collecting Highwaymen art, Lightle has amassed an encyclopedic knowledge of the group he excitedly shares with visitors who can make an appointment to see the work through his website. Lightle buys and sells artwork, but his greater passion is for sharing the story of the Highwaymen and promoting their paintings.

Highwaymen Art Specialists, Inc. represents the estates of Newton and a fellow original member, Willie Daniels. When Roy McClendon makes a public appearance at a museum or show, it’s almost a certainty that Lightle drove him there.

The Museum

A.E. “Bean” Backus established his reputation as Florida’s premiere landscape painter long before the Highwaymen came along. As luck would have it, he lived and worked in the Ft. Pierce area too.

While Backus only formally gave instruction to Alfred Hair – the Highwaymen’s other leading member – he opened his home and advocated for all members of the group. His support of Black artists was unprecedented for a white man in the mid-century South.

The A.E. Backus Museum in Ft. Pierce displays classic examples of Backus paintings which, upon first glance, prove the depth to which the Highwaymen owe him for their distinctive style.

Ft. Pierce has also designed a Highwaymen Heritage Trail allowing visitors to see for themselves locations around town important to the group’s story.

The Restaurant

At the seaside Ocean Grill back in Vero Beach (1050 Beachland Boulevard), Backus and the Highwaymen share space. Backus frequented the now-historic location. Fine examples of his paintings can be found throughout the restaurant and bar – unlabeled originals which would surely fetch mid-five figures at auction – passed by daily with nary a second look from hundreds of tourists.

Directly over the hostess stand, taking pride of place, hangs a moody, nocturnal seascape painted by Florida Highwaymen James Gibson. It’s not marked either. Of the few diners who even notice it, many likely assume it’s a knockoff or figure it comes from a department store.

It’s not.

It’s the real thing.

The Highwaymen live on in this part of Florida, if you know where to look.

When visiting Vero Beach and Ft. Pierce, my preferred hotel is the Kimpton Vero Beach Hotel & Spa right on the water, a block from the Ocean Grill.