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June 24, 2025

Chestertown Spy

Nonpartisan and Education-based News for Chestertown

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9 Brevities Archives

Chestertown Flashback: Captain Lillie Mae Flowers

May 30, 2025 by Historical Society of Kent County 1 Comment

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In this week’s Flashback Photo, we look forward to summer days on the Chester and the Bay, following the lead set by Captain Lillie Mae Flowers, pictured here circa 1939 aboard her vessel Chester. At the age of 22, Flowers became the youngest female sea captain, according to The Kent News of Saturday, July 22, 1939, which called her “A comely lady, slight and lissome.” The 1989 announcement of her death in a local newspaper noted that she “had been to the East Indies and sailed through storms. Chesapeake Bay storms, she said, were the worst of all.” The same article reported that she was the subject of a question on the television quiz show Jeopardy! but none of the contestants could name the youngest female sea captain.

If you have additional information or stories to tell about Captain Flowers, or other local sea captains, please share them in the comments below, or send them to [email protected].

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 9 Brevities, Archives

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Letters to Editor

  1. Inez Thompson says

    June 1, 2025 at 8:05 PM

    I remember going to visit her when she was married to Tilghman Meredith (some distant relative of my father) when they lived in Worton. I was in elementary school and easily impressed by her red hair, her fancy name and stories of being a tug boat captain. i have tried to find more information about her, but this picture is the first i have seen. I remember her telling us how she was the inspiration for the story of Tug Boat Annie. I am not sure if that is true or not.

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