This exhibition explores the improbable story and prodigious output of the Florida Highwaymen, an amorphous group of primarily self-taught African American artists who forged often lucrative careers as landscape painters against the backdrop of racially segregated Jim Crow Florida. Hailing largely from the communities of Fort Pierce and Gifford along the Atlantic coast of Florida, the Highwaymen produced hundreds of thousands of expressive and shockingly vibrant landscape paintings that captured the rapidly disappearing natural beauty of their region from their emergence in the late 1950s through the early 1980s. Denied access to gallery representation and excluded from the mainstream art world, the enterprising Highwaymen painters adopted a model of itinerant distribution, peddling their riotous, often rapidly produced oils, almost always still wet and priced to sell at around $25, on average, wherever they could—door-to-door, in doctor’s offices, bank lobbies, and shops—or to road-tripping tourists out of the trunks of their cars parked on the side of the interstate. Building on a tradition of American landscape painting that traces its roots back to the nineteenth-century tropical Floridian fantasias of artists like Winslow Homer, George Inness, Martin Johnson Heade, Hermann Herzog, and Thomas Moran, the Highwaymen painters reinvigorated the form, bringing fresh energy and an unrestrained color palette to bear on otherwise conventional scenes of swaying palm trees, polychrome sunsets, and breaking waves. Their exuberant art fundamentally shaped popular perception of the Sunshine State and provides lasting documentation of Florida’s disappearing natural paradise.
Unless otherwise noted, all works in this exhibition are drawn from the collection of Jonathan Otto (PA’75 and P’24 and P’27).
Generous support for this exhibition has been provided by Bernard I. Lumpkin and Carmine D. Boccuzzi and the Arthur and Vivian Schulte Exhibitions Fund.
A Note on Terminology
The term “Highwaymen” was not used to describe the group of Black artists responsible for these once ubiquitous Florida landscape paintings—either by themselves or others—until writer and historian Jim Fitch discovered their work in antique shops and flea markets throughout Florida during the early 1990s. Never seeing themselves as part of a unified, artistic school, some artists retroactively given the distinction of being a Highwayman bristled at the term in large part due to its association with criminality and its misleading implication of a unified movement. Interest in the work of these painters grew throughout the ’90s and Gary Monroe’s 2001 book The Highwaymen: Florida’s African-American Landscape Painters introduced the work of the Highwaymen to a broader audience. Monroe’s publication, consequentially and controversially, specifically defined the Highwaymen as a group of twenty-six artists—twenty-five men and one woman, excluding several artists who failed to meet Monroe’s criteria for inclusion. In 2004, the twenty-six artists were inducted into the Florida Artists Hall of Fame and, since then, the paintings of the Highwaymen have skyrocketed in value and collectability, with many artists coming out of retirement to meet the newfound demand for their work.
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“For all the communion the show can offer with individual works, its power lies in something much larger and more powerful — in how, in a time of severe repression, a creative impulse shared across a community of the like-minded can start to look something like freedom, made by hand.”
— Murray Whyte, The Boston Globe, November 13, 2025
On WGBH’s The Culture Show, co-host Jared Bowen and Addison Gallery curator Gordon Wilkins explore the Florida Highwaymen, the group of Black painters who turned Florida’s wild horizons into some of the most sought-after landscapes of the 20th century. Their vibrant scenes—sunrises, storm fronts, and stretching marshland—are now the focus of a major exhibition at the Addison. Bowen and Wilkins discuss the artists, their hustle, and the legacy they carved outside the mainstream.
video
In this Zoom webinar, Curator Gordon Wilkins explores the work of the Florida Highwaymen. The loosely affiliated group of 26 African American landscape painters sold their vivid and expressive tropical scenes door-to-door and out of the trunks of their cars along the coastal roads of Eastern Florida from the 1950s through the 1980s.
This program was presented in partnership with Andover’s Memorial Hall Library (recorded on October 1, 2025).
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