Five young women have begun a year of representing their hometown after being crowned the 2026-27 queens of the Miss Leesburg Scholarship Program during its 40th annual pageant.

Madison Aniello was crowned Tiny Miss Leesburg, Myrcella Ciceri was named Little Miss Leesburg, Raegan Mallory earned the Junior Miss Leesburg title, Harper Richey was crowned Teen Miss Leesburg, and Callie Braun was named Miss Leesburg.

The pageant was held Saturday, Sept. 12, at Leesburg High School, marking four decades since program director Linda Watts founded the organization to give local girls an opportunity to represent their community.

“It was something that 40 years ago, Leesburg didn’t have,” Linda says. “I was asked, ‘Why isn’t there a Miss Leesburg?’ and so from there, I got the city’s approval to use the name, organized and started it.”

Today, the nonprofit program includes five age divisions spanning elementary through high school. Winners serve for a year as what Linda calls “little ambassadors” for Leesburg, taking part in city and chamber events, volunteer projects and other community activities.

As part of the pageant celebrations this year, Linda was also honored for founding the program with a legacy brunch that brought back queens from as far back as the very first pageant.

“We held our Miss Leesburg Legacy Brunch to honor Mrs. Linda and her incredible dedication to this program over the past 40 years,” reads a Facebook post on the Miss Leesburg Scholarship Program page in Linda’s honor. “Her love and commitment have helped shape Miss Leesburg into the program it is today, and we are so grateful for the legacy she has created.”

With that, the newly crowned queens already got to work within days of being crowned, participating in the program’s monthly food delivery for LovExtension and an event recognizing first responders.

The program also organizes service projects throughout the year, including a winter jacket drive for people in need, a food drive for the Leesburg Food Bank and a diaper drive benefiting a local pregnancy care center. Through its Adopt a Grandparent program, each queen also connects for a year with a resident at Vista Lake Assisted Living who may not have family nearby or receive many visitors.

This year’s queens bring their own interests and ambitions to their new roles.

Madison, 6, is a first-grader at The Villages Charter School who enjoys dancing, swimming and gardening and hopes to become a schoolteacher and dance instructor. Myrcella, 7, attends First Academy, where she is in second grade. She enjoys competitive dance, playing with her dog and practicing makeup and says she would like to work at Starbucks when she grows up.

Raegan, 12, is a sixth-grader at Umatilla Middle School whose interests include cheer, baton, dance and babysitting. She hopes to major in business management and become an entrepreneur and makeup artist. Harper, 15, is a sophomore at The Villages High School who enjoys dancing, singing, attending Broadway shows and learning to drive. Her ambition is to become a nurse.

Callie, 17, is a senior at First Academy. She enjoys dance, cheer, guitar and boating and hopes to become a fashion marketing manager.

Scholarships and education remain a major part of the program’s mission. This year, Harper received a $1,000 scholarship as Teen Miss Leesburg. In the Miss division, $8,500 was awarded among four contestants, including $5,000 to the winner, $2,000 to first runner-up, $1,000 to second runner-up and $500 to third. Winners in the Tiny, Little and Junior divisions each received $250.

The scholarship fund began in 1997 and Linda says the program has since awarded $268,000. Over its 40-year history, 185 young women have spent a year representing Leesburg through the program.

For Linda, those numbers represent generations of young women and a community that has helped sustain the program.

“It’s a community effort, and to me, it’s just been a blessing because I can see how much we have done and how so many people have benefited.”