Miss Dreamsville and the Lost Heiress of Collier County One
Dolores Simpson was a woman with a past. Now, depending on your age and where you’re from, you might interpret that in a number of ways. Let me assure you, however, that in the southern part of the United States of America, in a certain era, this could mean only one thing: man trouble.
This affliction spares few women. Even maiden ladies and great aunties—the ones who smile and nod on the porch, contentedly snappin’ peas—have stories of youthful turmoil and shattered dreams.
Dolores Simpson, unfortunately, had what my mama used to call serious man trouble. After leading a questionable life in Tampa, Dolores came back home one summer day in 1939 with all her worldly goods in a satchel under one arm and a brand-new baby boy in the other.
Yes, indeed. Serious man trouble.
Home, for Dolores, was one hundred and twenty miles south of Tampa in God’s forgotten paradise, Collier County, which is bordered by the Gulf of Mexico on one side and the edge of the Great Everglades Swamp on the other. In those days, Radio Havana in Cuba was the only station that could be heard on the wireless and alligators outnumbered people by at least ten thousand to one.
Dolores’s destination was an abandoned fishing shack that once belonged to her grandfather. The shack sat on stilts on a tidal river which was so wild and forbidding that no one with an ounce of sense would try to live there. Still, it was all Dolores knew. She had failed at city life. She had failed at pretty much everything. The river was a place where she could protect her secrets and nurse her frustration with the world.
And there she stayed, alone except for the son she raised, for twenty-five years.
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I, TOO, HAILED FROM COLLIER County, but instead of the river or swamps I was raised nearby in Naples, an itty-bitty town with a sandy strip of beach on the Gulf.
I barely knew Dolores Simpson. She was, shall we say, reclusive to an extreme. My only knowledge of her was that she had once been a stripper but now hunted alligators for a living. If she had been a man she would have been admired as a fearless frontiersman.
I wouldn’t have known even this much, nor would I have met her, if not for her son, Robbie-Lee. In the late summer of 1962, he and I became friends when we joined a new book club called the Collier County Women’s Literary Society. To its members, the club provided a sanctuary of sorts. Each of us was a misfit or outcast in town—in my case, because I had come back home after a divorce—but in the book club we discovered a place to belong.
It is one of the ironies of life that being part of a group can, in turn, lead you to find strength and independence as an individual. That’s exactly what happened to Robbie-Lee and me. After a year in the book club, we decided it was time to follow our dreams.
For Robbie-Lee, who loved the theater, the only place on his mind was New York City. He spoke endlessly of Broadway and was determined to get a job there, even if it meant sweeping sidewalks. Dolores, whose maternal instincts kicked in with a mighty roar at the idea of him leaving Collier County, objected to his planned departure, but lost the battle. Robbie-Lee caught a northbound bus on a steamy August morning in 1963.
At the same time Robbie-Lee went north I set off for Mississippi. I was hoping to learn more about my mother, who was born and raised in Jackson. Mama had died without telling me certain things. She never talked about her family, or how she met Daddy, or when and where they got married. All I know is they got hitched at a Methodist church because Mama insisted on having a bona fide preacher conduct the ceremony. They left Mississippi and came to Florida because Naples was Daddy’s hometown.
What I hoped to find was kinfolk. An aunt or uncle, perhaps. Or maybe a cousin. Since I was a small child, Mama and I had been on our own. It’s painful to say, but Daddy up and left us. At least I hoped to find out why my name is Eudora Welty Witherspoon—“Dora” for short. I could only guess that Eudora Welty, the famed Mississippi writer, had been a friend of Mama’s when she was growing up.
As I said, Mama never told me certain things.
I figured I’d go to Jackson for a few weeks or at most several months, but before I knew it I’d been away from Florida for a year. I had made more progress finding out about Mama and her people than I ever could have imagined. All I needed was a little more time to wrap things up and settle them properly. I had a job shelving books at the Jackson Library and I rented a small room in the home of a widow named Mrs. Sheba Conroy. I planned on giving proper notice—I didn’t want to leave anyone in the lurch—then head home to Naples.
And then the telegram came.