Chesnie Caldwell named Miss KY Teen America

The moment Chesnie Caldwell learned she won the Miss Kentucky Teen America pageant was captured. She will continue on to compete in the Miss Teen America pageant, held in July.

Chesnie Caldwell didn’t give up. And because of that, she has earned her crown.

The 15-year-old sophomore from Southwestern High School was crowned as Miss Kentucky Teen America at their pageant held March 16.

It was her second year competing in the pageant, which is open to girls ages 14 through 18. When Caldwell earned third runner-up in 2018, she said she learned from that experience.

“Last year I went in there, I was really intimidated because I was only 14 years old. I was competing against people who are going into college and who could drive, and I’m barely in high school. So last year, I guess my confidence levels were low, and I was just intimidated by everybody.

“Then this year I went in there and realized you have to be confident in order to win, and that’s the skill I lacked last year.”

That confidence led to an unexpected emotion just before she went out onto the stage for the announcement of the winners.

“It was really weird, because usually I’m really anxious before they crown [someone]. You want it to be you, you pray that it’s you. And I remember right before I went out on stage, I had this calming feeling, like, even if I didn’t win, it was going to be okay. I was going to come back next year."

That calm turned to excitement, though, as the reality sank in that she had earned the crown.

Caldwell’s mother, Stephanie Hill, said more than a week later that she was still in shock.

“Very excited,” she said about her daughter’s win and the fact that it means Caldwell will be moving on to the national competition.

“I know that the pageants that she does, she does because they’re a good system and they will educate her.”

That includes the Miss Teen America pageant being held in Texas in July.

“I can’t wait to go to Nationals and meet everybody,” Caldwell said.

But she is also looking forward to attending Kentucky charity events and festivals, and learning more about her home state.

“Because as Miss Kentucky Teen America, we do a lot of community service projects, and you go make appearances at festivals and community events. So, being able to do that is very important to me because I want to learn more about what this state has to offer and what I can do with my title” she said.

While Caldwell has done the hardest work in getting to the national stage, she offered some thanks to others who surround her, including her “Number One Fan,” her grandmother, Wilma Hampton.

She also thanked Lexington makeup artist Champayne Wilson of Pop in with Champayne, who does Caldwell’s hair and make up for each pageant, and also offered thanks to the Miss Kentucky Teen America director, Jessica Glasscock.

The national competition is within months, and Caldwell and her mother still need to do a little bit of fundraising to assist on the journey. That’s why the two are planning a Kentucky Derby-themed Mother’s Day Brunch to take place at Pleasant Hill Baptist Church.

The duo are selling tickets for the brunch, scheduled for April 27 at noon.

Hill said there will be a silent auction, singers and a guest speaker.

The two can be contacted through Facebook, either on their individual pages or through the company page for Dreams Come True Characters.

Dreams Come True is Caldwell’s way of giving back to the community. The company was set up to bring Disney characters to autistic and mentally handicapped children – some of whom may not be able to get to Disney World in person due to an inability to handle crowded places

“It’s really important to me,” Caldwell said. “It’ something I’m really passionate about.”

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