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.
Remembering back to the1840s, Thomas Dabney's daughter wrote, "Many gentlemen at Pass Christian owned fast-sailing yachts, and during the season, fortnightly regattas were held, in which the entire population felt deeply interested, as almost everyone owing a yacht entered in for the race."
An Antebellum statement by a northern governess reads that, "The grand regatta of the Southern Yacht Club came off today and created fine sport with a beautiful breeze prevailing."
"The steamer Mobile came from Biloxi with a large array of ladies and gentlemen, accompanied by a fine band of music, to witness the race, which added to the excitement. The race was for 15 miles which sailed around a triangle of seven and one-half miles. The prize for the first class was a silver pitcher, to the second, two silver goblets, and for the third, a silver cup. The boats were placed in position at 12 o'clock. A gun fired as a signal for them to get underway. The first boat finished the course in two hours, 20 minutes, and 14 seconds."
In 1937, the newly formed Skipperette Club voted Mrs. Peggy Gause as its Commodore. In 1938, the Knost Regatta for female skippers came into existence, honoring Bernard Knost, and has since continued as an annual event of the Pass Christian Yacht Club.