Yachting in the South was born at Pass Christian. The first regatta promoted by R.H. Montgomery, manager of the Pass Christian Hotel, was held on July 21, 1849. Citing a New Orleans' news article from the "Crescent" on that date, "It was a gala day at the Pass. The quiet harbor was thronged with boats, gay with streamers, and manned by athletic crews..." Responding to the challenge were a dozen contestants. The Stingaree Social Club of New Orleans had acquired a new cabin sloop, resulting in their qualifying for the 25 mile race. Twelve sailboats, representing as many towns, had lined up at the start of the triangular course. Although the Stingarees lost, coming in third, the Eliza Riddle was christened
The Flirt of Biloxi won the silver pitcher, and the Anna of the "Pass" finished second. All had a wonderful time, and they ended the evening by organizing the Southern Regatta Club with Pass Christian as headquarters. The enthusiasm resulted in officers being elected the following summer, with Tom S. Dabney as its first president. The Southern Yacht Club of New Orleans originated from members of this association.