A benefit screening of The Flight of Jackie Cochran brings a national story home to Walton County for an intimate evening of film, conversation, and purpose

On a spring evening in Freeport, as the light softens over the bay and conversations gather their rhythm, a story nearly lost to history will take flight once more.

On April 18, the Steamboat Landing Clubhouse will open its doors for a benefit screening of The Flight of Jackie Cochran, a documentary that traces the life of a woman who refused the limits of her time and, in doing so, quietly reshaped it. The evening begins at 6:30 with a cocktail hour, the kind that invites a slower pace and familiar faces, before settling into a 7:30 screening followed by a conversation with the filmmakers. There will be a silent auction, generous fare, and the easy hospitality that defines gatherings along this stretch of HWY 331.

Hosted by Grit & Grace, Inc., the screening is part of the Wings of Courage Tour, a growing national effort rooted, perhaps unexpectedly, in Walton County. What began here as a grassroots undertaking has stretched outward, carrying Cochran’s story to museums, universities, and airfields across the country. From the WASP Museum Homecoming to the Museum of Flight and beyond, each stop invites audiences into a shared act of remembering.

Cochran’s life resists easy summary. She rose from poverty with little formal education and went on to become the first woman to break the sound barrier. During World War II, she helped establish the Women Airforce Service Pilots, creating pathways that had not previously existed and might not have, without her insistence, for years to come. Hers is a story of persistence, certainly, but also of vision. She saw not only what was, but what could be.

The film, directed by Jessica Anderson and produced by Nancy Hasty, carries that sensibility. It has earned national recognition, including honors at the Orlando Film Festival and a Suncoast Emmy nomination for Best Historical Documentary. Yet its power lies less in accolades than in its ability to draw a line from past to present, reminding audiences that history is not fixed. It is something we return to, reconsider, and carry forward.

In Freeport, that return will feel personal. The room will hold just one hundred guests, an intentional closeness that mirrors the spirit of the tour itself. There is something fitting about that scale. Cochran’s achievements were vast, but the telling of them often happens in rooms like this one, where stories are not broadcast so much as shared.

Along HWY 331, where community still gathers with purpose, the evening offers a chance to sit with a remarkable life and, perhaps, to leave with a clearer sense of one’s own.

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