2021 Pioneer Festival!

Join us in Downtown Winchester for the 42nd annual Daniel Boone Pioneer Festival Saturday, September 4th from 9:30 AM to 6:00 PM and Sunday, September 5th from 10:00 AM to 5:00 PM.

There are a variety of wonderful events throughout Clark County, but no event draws people to the community like the Daniel Boone Pioneer Festival. For many this festival serves as a homecoming, bringing family from all over the nation to celebrate our heritage. For others this is the opportunity to travel to Winchester and experience nationally renowned entertainment and handmade arts and crafts.  

The festival draws approximately 20,000 people and has been honored multiple times as one of the Top 10 Festivals in Kentucky and also one of the Top 20 Festivals in the Southeast United States. Not only is this weekend filled with activities for the entire family it also serves as the largest fundraising weekend for many of our local non-profit, civic and academic groups. 

Here’s what you need to know about this year’s festivities:

We’ve Moved!  This year’s festival will be held along Main Street in downtown Winchester, the heart of our community. While we’ll miss the familiarity of College Park, being downtown allows us more room to socially distance. The beautiful historic buildings, boutiques, restaurants and gift shops provide the perfect backdrop for this year’s festivities.

Make life simple, ride the Shuttle!  Shuttle parking is at R.D. Campbell Jr High School. Shuttles will run continuously throughout the day. Once onboard you can hop off the shuttle at any of the stops downtown, just look for the shuttle flags. Don’t want to walk from one end of Main to the other?  Hop on the shuttle and save a few steps. Hands full? The shuttle allows you the flexibility to drop your stuff off at your car and come back for another round. Handicapped Parking will be available onsite.

Shop ‘til you Drop!  With over 100 arts and crafts vendors selling their handcrafted wares you’re sure to find several treasures and maybe even a gift or two. There are a wide variety of offerings including: jewelry, clothing, art, photography, garden items, bourbon honey, and yummy foods.

Come Hungry!  Downtown Winchester has eight locally owned restaurants each offering different specialties and many are on the Beer Cheese Trail. We have 15 additional food vendors with festival favorites and two beer vendors.

Don’t Miss the Kids Area Located at the Bluegrass Heritage Museum. There will be a FREE petting zoo for the kiddos. Inflatables, games, and face painting will also be onsite. Take a moment to tour the museum filled with exhibits and stories of our past.

For your Entertainment Live music will be at Courthouse throughout the weekend. Saturday afternoon the Talent Contest, a long-standing tradition, showcases regional and local talent with prize money awarded. Bring a chair and enjoy the show.

Walk or Run for a Cause Friday evening the GRC Cheerleaders will host a Walk to benefit National Alliance on Mental Illness and Saturday morning GRC Track and Field sponsors the David Borden 5K Run

Dance the Night Away The Street Dance is Saturday evening from 6-9 PM featuring the Torques!

Community Worship Service This will be held at 8:00 AM, Sunday, September 5th in front of the Courthouse. This years’ service will be led by Reverend Jerry Johns of First Christian Church in Winchester. Bring a chair and stay after the service to enjoy the day’s festivities. 

Stay Safe, Stay Healthy! Relocating to downtown provides ample room to spread our vendors apart to avoid congested lines. We ask our vendors and participants to abide by local health guidelines and be respectful of one another.