It’s October, We Can Finally Talk About the Big Day..No Not That One

Jenny Wiley Ampitheatre, Tarzan
The stars come out at night at Jenny Wiley Amphitheatre
June 6, 2018
15 Unique Gifts For Mom 2018
November 20, 2018
Show all

It’s October, We Can Finally Talk About the Big Day..No Not That One



The days have been ticking down for the leaves to start dropping, the wind to slightly chill, and the decorations to be proudly prepared, all to signal that the time you’ve been waiting for is finally here. The calendar has lifted, October is here! So, the special costume you’ve been holding in the back of your closet all year is ready to see the light. That’s right the stretchy pants can make their grand return! Oh, wait, we may need to hit the brakes as it appears you might be thinking we’re talking of the ole Halloween. While, we love candy and wooden boo cutouts as much as the next, we’re talking about the great, wonderful days in October known as Jenny Wiley Festival! Yes, the days of sweet funnel cakes (hints the stretchy pants), community contests, Powwows, artists lining the streets, and carnival lights filling the sky are finally here!

The festival has been a staple of Prestonsburg and Floyd County for 36 years, but the tradition dates back much further. The woman in reference within the festival title was a fierce pioneer as she escaped Native American captivity in 1790, setting a tone for Appalachian people and becoming a living testament to the will of a woman. Our community has certainly kept the same desire to survive and succeed since the days of her emancipation. Now, through Jenny Wiley Festival, we celebrate and lift up our town’s heritage. It’s like the old saying goes, there’s nothing like a healthy pumpkin race to bring people together. That’s not a traditional saying? Perhaps it should be.

We love seeing the smiling faces floating through town. We especially enjoy the notion of thousands connecting with artists, new start-up businesses, and established downtown businesses. As much as the week is dedication to fun and food, it’s also about creating partnerships that last long past Saturday. What do you look forward to the most? For us, we can’t wait to stroll through all of the decorated pumpkins on our way to pick up a new handmade coffee mug for our must have apple cider this fall! You can definitely catch us by the stage for a weekend packed with FREE concerts—featuring rock, bluegrass, gospel, folk, and country artists! And, of course, we can’t miss out of the unique foliage views from the top of the ferris wheel.

You have the freedom to mold the four days of fun into as much or as little as you want it to be. Treat yourself by shopping with the endless hand-crafted vendors or enjoy all of the free performances, contests, and events offered; eat all of your favorite indulgences or get pumped for our 5k; grab a vip seat or move your boots to the music! There is something for all as we celebrate YOU during this Jenny Wiley Festival!


Don’t miss this packed lineup of events!

Day 1, Wednesday, October 10

10:00am Senior Citizen Bingo Prestonsburg Healthcare Center
6:00pm Casey’s Rides Carnival Open
6:00pm Pet Show—Craft Tent – Animal Shelter (606) 886-3189
6:00pm Festival Opening Ceremony—Stage
6:15pm KY Opry Junior Pros
7:30pm Big Sandy Singers

Day 2, Thursday, October 11

10:00am Arts & Crafts Tent & Marketplace Open
10:30am Food Vendors Open
11:00am Lunchtime Entertainment—Big Sandy Idol
5:00pm Candle Light Vigil—Stage
5:30pm Gospel Night—Stage—Hosted by David Taylor
Lee Collins
Blanton Sisters
Little Paint Quartet
Heaven’s Sake
Slone Family

Day 3, Friday, October 12

9a/12p/6p Indian Pow Wow
10:00am Quilt Show—Historic Samuel May House
10:00am Arts & Crafts Tent & Marketplace Open
10:30am Food Vendors Open
11:00am Lunchtime Entertainment—Big Sandy Idol
12:00am Fun Zone Opens—Downtown Fountain
12:00pm Pumpkin Decorating Contest Drop-off Deadline—Downtown Fountain
6:30pm Cornhole Tournament—City Hall Michael Tussey (606) 371-2967
6:00pm Friday Night Entertainment—Stage
Sons of FM
Bek & the Starlight Review
Luna & the Mountain Jets

Day 4, Saturday, October 13

9:00am Dr. Ron Leslie 5K Run/Walk for Diabetes (606) 886-2788
9:00am Car & Bike Show—First Commonwealth Bank
10:00am Quilt Show—Historic Samuel May House
10:00am Arts & Craft Tent & Marketplace Open
10:30am Food Vendors Open
11a/2p/5p Lumberjack Show
Sponsored by Layne’s ACE Hardware
11:00am Beatin’ Down the ‘Burg Stereo Competition
Shay Mullins—(606) 331-1865
11:00am Jenny Wiley Pumpkin Derby—East Court Street
(606) 874-7061
11:00am Fun Zone Opens—Downtown Fountain
12p/6p Indian Pow Wow
3:00pm Parade—Lineup begins at 2pm on S. Lake Dr.
5:00pm Saturday Night Entertainment Begins—Stage
5:00pm Troy Burchett
6:00pm Clay Jamerson
7:00pm Garland Rogers & Friends