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The word ‘legend’ gets thrown around all too loosely at times. 

However, in Winchester, the term was attributable to Holly VanMeter. 

VanMeter, who died at age 86 on Wednesday, Feb. 19, was paid tribute to as reactions poured in from throughout the community. 

“I am devastated!!!” wrote Mason Rhodus, owner and operator of Mason on Main. “Holly[,] I will miss all the laughter we have shared the last ten years. Your friendship meant more to me than you could have ever known!!! I LOVE YOU HOLLY.” 

VanMeter, who was a mother, grandmother, and great-grandmother, was the first ever president of the Winchester Art Guild when it was formed as a 501(c)(3) organization in 1974. 

“Holly brought almost a nationwide focus to the arts here in Winchester…she is well known and well loved,” said Ken Howard, current president of the Winchester Art Guild. 

A self-taught artist, VanMeter worked in several disciplines, including watercolor paintings, postcards, notecards, and more. 

She received statewide recognition for her work decorating a pair of Horse Mania fiberglass horses. 

VanMeter also was influential in inspiring and guiding the work of others throughout the community. 

“She was very good at tutoring and mentoring and instilling a love of art with other artists, especially young artists,” Howard added. “She loved to help folks, and she loved to be a part of the community.” 

In the hours following her passing, Whiskey and Wiles Photography’s Facebook page recognized VanMeter. 

“I couldn’t let the clock hit midnight on this cold day without acknowledging that a #winchesterky legend has passed on. Ms. Holly VanMeter meant many things to many folks around our town. She had a very special connection to Gallery66 and Whiskey and Wiles Photography’s new home on Main Street,” said one post, which featured pictures including one of VanMeter sitting at a table with various works. 

Yet no discussion of VanMeter would be complete without discussing her impact on the Daniel Boone Pioneer Festival, a now annually-held event in Winchester featuring numerous arts and crafts vendors and more. 

“She was the impetus that really got that going, and maintained it, and sustained it,” Howard said, adding that it grew exceptionally thanks to VanMeter’s influence. “I don’t think that we would be where we are without her leadership and without that first push with the Daniel Boone Pioneer Festival.” 

VanMeter’s character stood out as much in the community as her art work. 

“The only thing that [surpassed] her talent [was] the goodness and kindness of her heart,” Howard said. “She never met a stranger. She always was sweet to everyone and kind to everyone.” 

On his personal Facebook page, a local realtor showed a card of a print VanMeter painted and had sent him when he first began his career. 

“She wrote inside of it…words of encouragement and how happy she was for me,” he said. “I will always treasure this. Rest in peace sweet lady. You were a blessing to Winchester.” 

VanMeter was previously a Grand Marshal of the town’s annual downtown Christmas parade. 

Her obituary, shared by many including Magistrate Robert Blanton, received hundreds of responses from individuals. 

When asked what he hoped – among many characteristics – others might remember the most, Howard was prompt with a response. 

“Her love,” he said. “Her love for others. Her love for community, and her love for the arts…and for passing that love down to others.”