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Headland, Alabama - Gem of the Wiregrass
Headland, Alabama - Gem of the Wiregrass
Headland, Alabama - Gem of the Wiregrass

Miss Headland 2018-2019 – Jolie Money won the title on the 80th anniversary of the pageant. She won the Written Communication & Interview Awards in the March 2018 pageant. She made the top 10 finalists in the current 2018 Miss National Peanut Pageant. Jolie attended Headland High School but completed her education by being home schooled.

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