Seven things you didn’t know about the Daniel Boone Pioneer Festival

The 44th Annual Daniel Boone Pioneer Festival takes place in downtown Winchester on Labor Day Weekend, September 2 and 3, kicking off on Friday, Sept. 1, with an evening street dance—also downtown.

If you’ve attended past festivals, you already know how much fun the festival is with live music, handmade arts and crafts, a huge variety of festival foodie faves and lots of family fun . . . but there might be a few things you didn’t know. Read on!

1. It’s been around, and bounced around

The festival has been around since the first Susan B. Anthony coin was minted in the U.S. (representing the first time a woman appeared on a U.S. circulating coin) and the last iconic Volkswagen Beetle was manufactured in Germany.

Founded in 1978 by the Winchester Art Guild, the festival began as a way for local artisans to display and sell their handicrafts. In those early years, the festival was held on the steps of the Clark County Courthouse.

In the 1980s, as the number of attendees swelled, the festival was moved to College Park. Since both Mother Nature and world events seemed to conspire against it in that location—the former in the way of rain and mud, the latter in a global pandemic—the festival was moved again in 2019 . . . back to downtown where it has settled in very nicely along Main Street.

2. Festival admission is free

Yes, free. And it always has been.

3. 150+ tents mean a HUGE variety of arts, crafts, foods and fun

Booths, booths and more booths—lining downtown Winchester as far as the eye can see and filled with all sorts of goodies: pottery, ceramics, art, jewelry, body products (lotions, beard oils, soaps, more), bourbon barrel items, t-shirts, seasonal décor, gourd art, macrame, Shaker-style brooms and boxes, leather items, wood puzzles, painted rocks, heirloom children’s clothes, quilts, and other art and handicraft items; country ham sandwiches, steakbombs, blooming onions, pork rinds, hand-dipped corndogs, pulled pork cheese fries, famous crack chicken, fried Oreos, funnel cakes, ice cream, iced coffee, shaved ice, bubble tea and so. much. more. Find your favorite Winchester artists and vendors as well as those from all over Kentucky and from Ohio, Tennessee and Georgia, too.

4. New community gallery space opens during the festival

The Gallery Above, a free community space, presents the “Minds of Many,” a showing of more than 70 artists from the Winchester community. The multimedia event, held in the historic McEldowney Building at 5 Cleveland Avenue, will open its doors 10 a.m.-6 p.m. Saturday and Sunday during the festival, with the exhibition running through October 2023.

“Come celebrate the arts with us,” said Adam Kidd, co-director of the project goaled to make art accessible to the public. “The space will soon be accessible for artists to use and facilitate their own gallery shows.”

5. “Neon Hallelujah” artist headlines

Saturday evening’s headlining performer, county music star JD Shelburne, is excited to come to Winchester, the place Daniel Boone described, from atop Pilot Knob, as seeing “with pleasure the beautiful level of Kentucke.”

“Growing up in Kentucky and from playing on traveling sports teams across the Commonwealth to now touring full time—and getting to play hundreds of small towns across the Bluegrass— you can say I have seen my fair share of what makes Kentucky special and enriched in beauty,” said Shelburne.

Shelburne grew up about 75 miles west of Winchester, on a tobacco farm in Taylorsville, KY.

“A 120-acre family farm has been in my family for over 100 years, and one day it will be passed down to my brother and me,” said Shelburne. “Every inch of that land I grew up on runs through every single song I have ever recorded. I am proud of that and my heritage.”

6. 10:50 arrival . . . is that early, late? Nope! It’s right on time – here’s why

Winchester’s own 10:50 ARRIVAL trio is performing during Friday evening’s street dance, 7-9 p.m. Why 10:50? That is the time Gabriel, daughter of husband-and-wife harmonizers, David and Rebecca Jensen, arrived on scene, aka was born. Originally from Washington State, the family moved to Kentucky in 2020 to create beautiful music together.

“We enjoy playing music and singing together,” said David Jensen. “We have enjoyed Kentucky so far and have met so many nice people.”

Give a listen here, then plan to bust a move to 10:50 ARRIVAL’s tunes on Friday, Sept. 1.

7. Festival walk is for the dogs

The 2023 “Walk with Friends” is a fundraising event to support/raise funds for the Clark County Animal Shelter. The walk, hosted by the George Rogers Clark cheerleading squad, will begin at 8 a.m. on Saturday, Sept. 2, at 303 Hickman Street (at Lincoln Street). A small portion of the proceeds may go to walk organizer, GRC Cheerleading, and to GRC Girls Golf.

The Clark County Animal Shelter strives to lower the number of unwanted and abandoned animals in our community. It also strives to adopt all of its animals and works very closely with rescue groups and other organizations to ensure our animals are placed in the best homes possible.