The most famous prostitute of Punta Gorda was Miss Ollie Brackett. Ollie ran a “disorderly, bawdy house of ill repute” at the west end of Marion Avenue – in those days it was known as the bad part of town. Miss Ollie served a few very select customers herself and managed her “stable” of seven “ponies” who handled the majority of the clientele.
Back in the day there were several brothels here in Punta Gorda. It was a rough pioneer town populated with scores of unmarried cattle men, fishermen, railroad workers and tradesmen. Besides the houses with red lights, there were houseboats of girls on call for fishermen located in what was known as Whore Bay.