On the Road: Finding Inspiration in Florida’s Hidden Stories
The Springs: A Journey Into Stillness
This summer, James and I packed the car with little more than flip-flops, a cooler, and our curiosity, and set off on another adventure through Florida. We ended up in High Springs, a place that feels like stepping into another time — slow, unhurried, and surrounded by the kind of natural beauty that makes you breathe a little deeper.
The springs themselves are like liquid jewels, clear and cold, filled with a stillness that whispers history if you’re quiet enough to listen.
The Highwaymen: Florida’s Artists of Resilience
But beyond the water, we found ourselves chasing another kind of inspiration: Florida Highwaymen paintings. A group of 26 artists — including one remarkable woman — began painting Florida’s landscapes in the 1950s and ’60s. Royal poinciana trees, stormy skies, wide rivers — captured not on expensive stretched canvas, but on whatever materials they could find. Masonite. Canvas board. And most of all, Upson board — a humble construction material that became their window to the world.
They sold these works out of car trunks along the highways, often fresh with wet paint, at a time when galleries were closed to them because of the color of their skin. Their story is an essential chapter in American art and Black cultural history — a testament to resilience, vision, and determination in the face of barriers.
Learning Through Stories
As we’ve started collecting Highwaymen works, we’ve been privileged not just to acquire paintings but also to learn stories from friends and collectors who knew them — what it was like to work alongside these artists, to share in their lives, and to preserve their legacy. Each story feels like an oral thread tying us back to the art itself — as alive and vital as the colors on the board.
Our collection is growing, and with it, our respect deepens. These paintings aren’t just landscapes; they’re living history. They remind us of ingenuity, courage, and the will to create beauty against all odds. To us, they stand proudly among the great stories of American art, and we feel honored to help share them.
The Road That Connects Us
Driving through the remote parts of Florida where the Highwaymen once roamed, we saw what they saw: wild, untamed stretches of land that have changed little over decades. Palmetto scrub, sleepy towns, skies so wide they take your breath away. It gave us a glimpse into the world that inspired them — a Florida that feels both eternal and fleeting, fragile yet strong.
I couldn’t help but feel a kinship, translating all of this into my own artworks. On the drive home, I realized I have been painting women swimming in spring pools and rivers for many years now. Sometimes I feel like my work sees my future before I do. The springs represent beauty and freedom — and now I see, they’ve been guiding me all along.
Carrying the Story Forward
For me, that’s the joy of these journeys. It’s not just about finding a new spring or discovering a painting. It’s about gathering stories, connecting to history, and letting those experiences fold back into our own creative lives. Because art isn’t just what happens in the studio — it’s what we carry with us, from the water’s edge to the gallery walls, from one generation to the next.
If you’re nearby, come by Amanda James Gallery to see our growing collection and share in these stories with us. We’d love to show you the work, talk about the journeys, and keep this history alive together. The Highwaymen remind us that visibility matters, that representation matters, and that the brilliance of Black artists deserves to be seen, celebrated, and uplifted.