28th Annual Gamble Rogers Folk Festival



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At RLF, we often celebrate James Gamble Rogers II and his son Jack Rogers for their architectural impact on Winter Park and the surrounding communities. But did you know that our founder had a second son who left a different but equally enduring legacy?

James Gamble Rogers IV, the oldest son of James Gamble Rogers II, studied architecture at the University of Virginia for three years and, like Jack Rogers, was destined to join their father’s architecture firm. According to the Fretford Journal, Rogers was en route to a job interview at Cambridge Seven Design, a Massachusetts architectural firm, when he accepted a friend’s invitation to watch auditions for the Serendipity Singers, a popular folk group in New York. Rogers was unimpressed with the musicians who showed up, borrowed a guitar, and was offered a job singing and playing acoustic and electric guitars. As they say, the rest is history.

Instead of following the family business, he became nationally known as a folk singer as a member of the Serendipity Singers during the 1970s. A few years later, he left the group and moved back to Florida to concentrate on his solo singer and storyteller career.  Gamble was known for his original stories, written with a literary eye, southern humor, and finger picking prowess. He went on to perform across the U.S. and Canada, establishing relationships and performing with the likes of Jimmy Buffet, Chet Atkins, and Mike Cross. A well-respected folk singer, Gamble toured North American for nearly 30 years. His talent took him from raucous bars to folk festivals and eventually to the stage of Carnegie Hall.

Like his brother Jack, Gamble exuded a sense of responsibility to his fellow man. In 1991, while camping with his wife Nancy, Gamble attempted to save a drowning man at Flagler Beach and drowned at the age of 54. After his death, tributes poured in from friends and fans, including Jimmy Buffett, who dedicated his Fruitcakes album to Rogers’ memory. In the following years, the park at Flagler Beach was named the Gamble Rogers Memorial State Recreation Area in his honor, and the Gamble Rogers Middle School opened near St. Augustine, where he resided.

Gamble’s legacy lives on through the efforts of The Gamble Rogers Memorial Foundation. Each April, the Foundation hosts the Gamble Rogers Folk Festival in St. Augustine to commemorate his life and music, whose passion for balladry, storytelling, and the folk tradition have helped shape American folk music. To learn more about the event and purchase tickets, visit https://www.gamblerogersfest.org/

Credit: Winter Park Magazine, Florida’s Troubadour,

The Fretboard Journal, Gamble Rogers, The Oracle of Oklawaha