Concerts, Music Venues, News

Cumberland Mountain Fall Festival announces concert lineup

We are thrilled to announce the return of the Cumberland Mountain Fall Festival to downtown Middlesboro this October 1st and 2nd, 2021! For the first time in 40 years, it was cancelled last year. The staple event for downtown Middlesboro is something that folks across the region look forward to every year. Not only is there so much to do, with live music, tons of craft, food, and other vendors, car show, kids area, carnival, and so much much more…it’s completely FREE to enter (only thing that requires a paid ticket is the carnival). The event has been enjoyed by folks in the tri-state region for decades, and in the past few years has started to welcome in tourists from all over the nation. Situated in beautiful, historic downtown Middlesboro, in the shadow of the Cumberland Gap, the Cumberland Mountain Fall Festival is quintessential Appalachia in early autumn. 

“I remember going to the Fall Festival as a kid and just loving it. It has always been the biggest, most important event in downtown Middlesboro. I remember seeing John Anderson there as a high schooler when it was located at the community college, and remember thinking how great it was. But I’m so glad they moved it back downtown…that’s where it’s almost always held and it turns our downtown into a beehive of excitement. And this year, we’re looking to come back with a bang. I appreciate our current Mayor, Rick Nelson, for recognizing the importance of the event and making sure he brought in all our local entities like Tourism, the Chamber of Commerce, and Main Street Middlesboro to help the festival committee. In 2019, the event was a success but we had so few people actually helping put it on. That’s changed this year in a big way. We’ve got old faces and new faces to form a bigger group that get along well and are really itching to make this the best year ever.”

The Cumberland Mountain Fall Festival has been in Middlesboro over 40 years. Originally called Frontier Days, the name changed early on, but the focus remained the same. Then and now, it’s been about taking elements from a music festival, a craft fair, a county fair, and a car show and creating something totally unique. The event takes place in downtown Middlesboro, with the city blocking off Cumberland Avenue for five blocks and utilizing the city parking lot and some side streets. After a few slow years, it came back strong in 2019 and was poised to continue a strong run, then COVID hit.

But in 2021, it’s back and better than ever. This years music lineup is the strongest yet. It includes Memphis rockers Lucero headlining Saturday, with Morgan Wade, Justin Wells, Vintage Pistol, Drayton Farley, Brandon Fulson and Jade Robertson. Friday will be headlined by Kentucky blues rockers Magnolia Boulevard, with support from Joslyn and the Sweet Compression, Nolan Taylor, Logan Halstead, The Jenkins Twins, Low Water Bridge Band, and Danielle Walters. 

“This is a lineup I’m really proud of. Number one, it’s diverse. I love the concept of the Levitt AMP Series in how it showcases diverse music, and we’ve taken that same approach with this music lineup. Whereas something like Laurel Cove Music Festival is slightly more specialized with country, folk and bluegrass….with this years Cumberland Mountain Fall Festival Lineup you have rock (quite a bit of rock, actually), blues, bluegrass, country, folk, and R&B. There’s also a lot of bands we’ve not had down here before, probably most of them actually. And what I’m most proud of is that this lineup is a reflection of listening to folks I trust. We’ve got a group of nine or so friends that talk regularly, and all of them help out with our music scene here, always volunteering to do anything needed. All of them are great people who help out just because they’re great people and nothing more. So when thinking of this festival, number one I wanted to have a lineup that would be diverse and yet draw a big crowd, but also I just listened to them. They know live music better than any group of people I know and they’re folks I trust…so I took their input and kinda shaped the clay with it. So thanks to my cousin Daniel, Josh, Christina, Blake, Derek, Bill, Jason, Shane, Chris, and Alexis. Appreciate all those people so much for all the help they provide”.

While the concert is free, there is also going to be around 100 VIP seats available for purchase to the show. These seats will be up front right near the stage, and will also come with a limited edition poster as well. Stay tuned to the Facebook and website for more info on availability soon. 

While music is a big draw, there is so much more to the Cumberland Mountain Fall Festival. It’s something that can keep a family entertained all day. There’s a kids area with inflatables rides, and a different stage show or exhibit each year. There are a ton of different food and craft vendors from all over Appalachia. There’s a huge car show for auto enthusiasts of all kinds. There is a kid’s pageant hosted the week before that’s been a staple of the event for many years. The event features something for everyone. 

So mark your calendars for October 1st and 2nd and join the fun in downtown Middlesboro, KY.

If you have questions, or are interested in becoming a craft or food vendor, please contact 

Stay tuned for updates on our Facebook page and on