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

Little Miss Headland 1992-93 - Ariann Grimsley was originally named 1st runner up in the 1992 pageant where she won the Co-Sportswear Award. After Little Miss Headland, Adrienne Riley, moved away in late 1992, Ariann was given the title of Little Miss Headland and continued the reign until 1993 when she crowned the new Little Miss.

Ariann is the daughter of the late George Harold "Hal" Grimsley, Jr. (Haleburg) and Debra Janette Anderson (Columbia) and the granddaughter of George Harold Sr & Mildred Pelham Grimsley (Haleburg) and Thomas Fred & Hattie Janette Anderson (Columbia). She is a 2003 graduate of Chelsea High School in Chelsea, AL. Ariann is married to Lee Webster and they have two children together George (age 8) and Blaklee (soon to be age 4) and she is also stepmom to two, Tony Webster & Choe Webster Wade with a step-granddaughter, Evie Wade. She is a Certified Clinical Medical Assistant working for Dr. Megan Bullard at Columbiana Clinic in Columbiana, AL. Ariann and her husband also run a farm in Helena, Al called The Stables of Alabama.

Right photo was her Little Miss Headland contestant photo.

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