Little Miss Headland 1999-2000 – Anna Lewis won the title on the 40th anniversary of the pageant. She won the Interview, photogenic and best dress awards in the 1999 pageant. Anna is the daughter of George Lewis & the late Dawn Hardy Lewis (Tumbleton) and the granddaughter of Kyle & Dianne Hardy (Tumbleton) and George Sr. & Vivian Lewis (Abbeville). She is a 2010 graduate of Headland High School and is pursuing a career in Nursing. Anna is married to Cyle Hicks since 2011 and they have two sons, Eli & Fisher.
Trivia: Her sister, Abby Lewis, won Little Miss Henry County in 2001. Two of Anna's aunts were Miss Headland, Judy Hardy Skipper in 1967 and Zelda Hardy Oates took over the title in 1973-74 after Pam Flowers won Miss National Peanut Festival.