Fairest of the Fair 2003 – Holly Lane Freeman

Holly Lane Freeman.

A name many in Cookeville connect with leadership, forward-thinking, and dedicated community involvement.

But, did you know Holly was 2003 Fairest of the Fair, and also took home the crown as Tennessee’s Fairest of the Fairs?

With a heart for giving back fostered by her parents (Holly’s mother, a former competitor and seamstress who made many of her competition dresses, and her father, pageant judge and super fan), Fairest of the Fair and Holly Freeman was a natural fit.

She stated, “As a young woman, my parents instilled in me the importance of making a positive contribution wherever you can, so I did my best to use my time to play an active role in the fair and spread positivity as a representative of Putnam County. What I saw when the crown was on my head, circled back to the very reason I entered in the first place, giving my time, energy, and spirit to celebrating and serving my community.” Holly continued, “Then after being crowned Tennessee’s Fairest of the Fair, I traveled across the state to many other fairs, often as a judge or emcee of their pageant. I enjoyed experiencing different parts of the state that I may not have otherwise had reason to visit.”

As her life unfolded following the aforementioned victories, Holly entered various leadership roles (notably Cookeville CityScape), eventually finding a home at Opry Entertainment Group where she currently works with some of the most iconic venues and musical artists in Nashville and beyond. Throughout this career ascension, Holly has incorporated the skills and resilience she developed through Fairest of the Fair in her daily work, while also leaning on the leadership, volunteerism, and talent of subsequent winners.


“When I have been in positions of leadership for community events and needed responsible, engaging, and energetic volunteers, Shannon (Chair, Fairest of the Fair) was always one of my first calls. People wanted to see the Fairest of the Fair winners and I could confidently place these winners right beside leaders much older than themselves.” She added, “They’ve been placed in the same event roles as board members and civic leaders and always carried themselves with such grace.”

To conclude our interview, Holly voiced her mutual respect for those she competed against and a deep appreciation for what competitions like Fairest of the Fair truly represent.

“If you haven’t participated in pageants before, you may not understand the friendships and camaraderie that can exist, even when women are competing against each other. But I always had a wonderful experience meeting young ladies with a similar passion for their communities from all across the state.”

She concluded, “I think the fair pageant still has an important role to play for the young ladies of our community. The opportunity to wear something that makes them feel beautiful while celebrating their accomplishments and what makes them special is a valuable experience. It’s good to feel beautiful on the outside but being smart, well-spoken, and confident in yourself is what will stay the course of time.”

– by Andrew Buckner, photo by Cris Stroud


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