By Randy Noles
Gamble Rogers
Gamble Rogers

Gamble Rogers was known as the Oracle of Oklawaha. Maybe a better nickname would have been the Poet of Park Avenue, although that moniker would not have embodied the rustic Old Florida flair that Rogers embraced.

The life and music of Rogers, the state’s most enduring troubadour, will be celebrated May 1, 2 and 3 during the Gamble Rogers Music Festival, held annually in St. Augustine. Too bad Winter Park, where Rogers was born and raised, hasn’t yet found a way to honor its folk singing native son.

Maybe that’s because most Winter Parkers these days know the name Gamble Rogers as that of an iconic architect, whose buildings helped define Winter Park’s quasi-European ambience.

James Gamble Rogers II was the singer’s father. During the course of a 60-year career, he designed many of the area’s most elegant homes and helped define the look of the Rollins College campus.

The elder Rogers’ son, however, chose a different path. After graduating from Winter Park High School in 1955, he enrolled at the University of Virginia.

He didn’t manage to graduate from there, though. Nor did he graduate from Rollins or Stetson University, both of which he attended for a time. He worked in his father’s architecture practice for a few years — but the lure of music was too strong.

So the younger Rogers began moonlighting as a folk singer, and played his first gig around 1960 at a folk club called El Caribe, which was located on Park Avenue North.

He later performed with a folk group in Tallahassee and, for a time, was a member of the Serendipity Singers, appearing with the group on The Ed Sullivan Show, The Tonight Show and Hootenanny.

But homogenized folk music wasn’t Rogers’ cup of tea. He embarked on a solo career, honing his stage persona and his storytelling skills, and earning a cult following with his original songs and his tall tales about Oklawaha County, which wasn’t really a place but a state of mind.

“Each and every one of the characters in my stories started out representing a specific person,” said Rogers, who was described as a combination of Mark Twain, Will Rogers and Woody Guthrie (if any of the three had been Floridians). “The characters may tend to be outlandish, but their statements resonate with a certain amount of horse sense.”

Never a superstar, Rogers nonetheless found a niche, appearing frequently on NPR and in concert at Carnegie Hall with Doc Watson. He was revered by intellectuals, who admired his facility with the language, as well as by rural Floridians, who provided fodder for his stories and songs.

Rogers died in 1991 while trying to rescue a child from drowning at Flagler Beach. He was only 54. It was an act of bravery that friends say was entirely in keeping with his character. He rests in Winter Park’s Palm Cemetery, in a wooden casket built by friends. There is a certain, well, serendipity to that.

For more information about the Gamble Rogers Music Festival, check Maybe one of these days we won’t have to drive to St. Augustine to attend a tribute to “Florida’s Troubadour.”

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