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At Tuesday night’s meeting of the Winchester City Commission, Commissioner Kitty Strode was quick to thank the actions of city employees – including the Department of Public Works and Winchester Police Department – for their aid at this previous weekend’s Pioneer Festival when hazardous weather struck at approximately 3:00 p.m. Saturday afternoon. 

“We couldn’t have done it without them,” she said, noting that 65 mile per hour winds were present on Saturday.

However, she was also quick to point out the community’s strong performance. 

“Every year. I’m amazed that this community pulls together”, she said. “It takes a village, but we happen to have a village!” 

With the community pulling together, the 2024 edition of the Pioneer Festival welcomed thousands over the weekend with arts and crafts, food, and much more for entertainment. 

“It goes back 45 years,” said Elizabeth Chalfant, member of the Daniel Boone Pioneer Festival Committee. “It’s been a real boom to the businesses downtown [and] the restaurants downtown to have it here.” 

Prior to the event taking place at its current event on Main Street, the Pioneer Festival had been held at College Park. 

On both Friday and Saturday, vendors found themselves stationed up and down Main Street, with many stopping to view what items they had to sell. 

In total, 195 spots were available, with approximately 140 arts and crafts people signed up as well as nonprofit organizations, a children’s area, food places, and more – plus a shuttle at Robert D. Campbell Junior High School taking individuals to and from the festival. 

Regarding arts and crafts – which to many are the highlight of the festival – Chalfant elaborated. 

“Everything’s to be handmade, and I visit every booth,” she said. “We try to have a good variety….they’re scattered out.” 

Among the craft vendors were Philip McIntosh, a Winchester native now living in Harrodsburg who sells brooms and boxes. 

“It’s kind of like a little homecoming. I saw lots of old friends and family and made even more friends,” he said. “I slice all my own wood. I cut everything out myself. All the handles I make myself, and I use machinery that comes from the 1800s.” 

Bourbon Sterling, originating from Paris, KY and selling a variety of jewelry – also held a booth. 

“You can wear it to bed, shower, sweat, work. It looks good enough to go out in,” said owner Megan Conway. “I haven’t been to [the] Pioneer Festival and I always wanted to come…I always heard it was a good festival.” 

Other arts and crafts vendors included West Woodworking, LLC, Hawaii Handmade Studio, Brichele Candles, One of a Chime, Day 8 Design, Illuminated Candle Company, Appalachian Sandcrafts, J Neal Woodworks, White Oak Creek Boutique, Crocus Creek Woodworks, Cliffside Ironworks, Shop Southern Designs, Tolliver Lighting, Dirty South Pottery, Penguin Pottery, and more. 

Not to be overlooked, food and drink vendors included Billy’s Pork Rinds, Kona Ice, Peppers-R-Paradise, The Food Dudes, Stuarto’s Olive Oil, Wild West Chili, and Kentucky Bad Dog Jelly, 

Nace Taylor of Scottsville, KY, who owns and operates South 4 Farms along with his wife, Sheila, was present to showcase a large variety of maple products. 

“We’ve expanded our inventory since we were here last. Now we’ve added a complete buttermilk pancake mix, [and] a hot and mild poultry tub,” he said. “We also have pure maple syrup…I think I’m the only [businessman] in Kentucky that makes the sugar butter and candy.”

Some local organizations – such as Humanities of Winchester and the Clark Coalition – also held a booth, while many local luminaries including Hannah Toole made an appearance. 

Plus, with inflatables as well as Rosie’s Ponies Petting Zoo, kids had plenty to be excited by. 

Certainly not least, with a variety of musical talents such as Dustin Knox and Randy Kaplan present and playing near the Clark County Courthouse, those attending could hear the upbeat sounds accompanying the atmosphere. 

“Some are beginners. Some have not been on stage very much. Some are veterans that [have] been on stage a bunch,” said Wallace “Gator” Harrison, who helps serve as a sound engineer for the event and coordinates with the event. “I look around for the newer acts that would love to…be here and try it out.” 

The event proved to be a success for many, including Tim Potter – who visited from out of town alongside his wife. 

“We like to just come to activities like this and check out the culture and…the food,” he said. “We really enjoy the whole city of Winchester.”