In the spring of 1981 Big Charlie Thornton came up with the idea, according to Lynn Stone, who remembers the night a group of local sailors and friends sat around her place at Grayton Beach, discussing the possibility of organizing a local Hobie Cat regatta. 

Charlie and Lynn had been sailing in Ft Walton Beach regattas, and he wanted to create a just-for-fun race as part of the local Fourth of July celebration. As the night wore on, enthusiasm for the event grew.

Lynn, a seasoned Hobie sailor herself, helped Charlie with the organization of the race and news soon spread throughout the sailing community. A twenty-dollar entry fee would guarantee you a place, T-shirt, and beer at the end of the race. The group unanimously agreed on Sunday, the fifth of July as the date.

Charlie remembers it well. "We talked about the name for the race to print on the T-shirts and someone came up with Rags to Riches. Grayton sailors latched on to the name 'Rags' since all of them were poor. Those of us down at Seagrove would lay claim to the 'Riches' - therein lies the joke." 

Excerpt from Rags to Riches Regatta by Carol McCrite, Of Days Gone By:  Reflections of South Walton County, Florida