The City of Middlesboro Kentucky

The City of Middlesboro Kentucky Welcome to the official page of the City of Middlesboro! Stay informed about city news, upcoming events, and ongoing projects.

We're here to keep our community connected and up to date on all the great things happening in our city. It is the intent of the City of Middlesboro to encourage discussion between the followers of this page and the City. We will do our best and strive to reply to questions presented by followers via comments and private messages as soon as possible during normal business hours. In some cases, individuals could be directed to the contact information of specific departments, staff members, and71-/or web pages for the best and most accurate answer. While this page is inclusive, it is also subject to comment restrictions inherent with pages. In addition, in accordance with this Social Media Policy, the following comments will not be allowed:

• Threats, personal attacks, defamatory statements, or those that are posted in an abusively disparaging or vilifying manner.

• Hate speech directed at race, color, gender, sexual orientation, national origin, ethnicity, age, religion, or disability.

• Fraudulent, deceptive, or misleading information.

• Obscene, vulgar, or profane language, pictures, or videos.

• Comments advocating illegal activity or posting of material that violates copyrights or trademarks of others.

• Violation of any local, state, or federal laws or is otherwise unlawful.

• Campaign materials promoting or opposing, individuals or political parties.

Agenda for September Meeting of the Common Council.
09/14/2026

Agenda for September Meeting of the Common Council.

🍂 MIDDLESBORO MOMENTS | SEPTEMBER 14–19September is moving right along, and there’s another full week ahead in the Magic...
09/14/2026

🍂 MIDDLESBORO MOMENTS | SEPTEMBER 14–19

September is moving right along, and there’s another full week ahead in the Magic City!

🎶 We’re nearing the end of the Levitt AMP Middlesboro season, with another Thursday night of free live music downtown.

🍁 The countdown is also on for the Cumberland Mountain Fall Festival, October 2–3! We’re just a few weeks away from welcoming fall to downtown Middlesboro with music, vendors, food, arts, crafts, and plenty to explore.

📍 And throughout the week, there are plenty of opportunities to get out, support our community, enjoy our parks and trails, and take in the first hints of fall around Middlesboro.

Here’s what’s happening around town this week. 👇

Just THREE Levitt Thursdays left! 🎶The 2026 Levitt AMP Middlesboro season is winding down, but we still have three night...
09/10/2026

Just THREE Levitt Thursdays left! 🎶

The 2026 Levitt AMP Middlesboro season is winding down, but we still have three nights of FREE live music ahead of us!

This Thursday, Jason Carter takes the stage in downtown Middlesboro, with support from the Gladson Family Band.

📅 Thursday, September 10
🎻 Jason Carter
🎶 Gladson Family Band
📍 Downtown Middlesboro
🎟️ FREE

Bring your chair, find your favorite spot, and spend your Thursday evening downtown with us. There are only a few concerts left before we wrap up this year’s series!

🚧 A reminder for downtown: Cumberland Avenue from 19th Street to 21st Street will close at 5 PM. All vehicles need to be removed from the concert block by 4:30 PM. Parking is available in the City Parking Lot off 21st Street.

Three concerts left. Don’t miss this one!

Scenic Wednesday 🌿There’s something special about seeing Middlesboro from above. 💙Nestled between the mountains, surroun...
09/09/2026

Scenic Wednesday 🌿

There’s something special about seeing Middlesboro from above. 💙

Nestled between the mountains, surrounded by green, and with just the first hints of a new season beginning to appear, this view is a pretty good reminder of just how beautiful our corner of Kentucky really is.

September looks good on the Magic City. 🍂⛰️

📍 MIDDLESBORO MOMENTS | SEPTEMBER 8–12There’s plenty happening around the Magic City this week! Whether you’re heading d...
09/08/2026

📍 MIDDLESBORO MOMENTS | SEPTEMBER 8–12

There’s plenty happening around the Magic City this week! Whether you’re heading downtown, supporting a local event, or simply enjoying these last days of summer, here’s your weekly look at what’s happening in Middlesboro.

🎶 Thursday — Levitt AMP Middlesboro
We’re down to the final few concerts of the season! Head downtown Thursday evening for another night of free live music and community fun.

📚 School is back in full swing!
Watch for buses, school traffic, student drivers, and little pedestrians as our local schools settle into the new year.

🍂 Fall Festival Countdown
The Cumberland Mountain Fall Festival is less than a month away! Mark your calendars for October 2–3 and get ready for a weekend in downtown Middlesboro.

☀️ All Week Long
Take advantage of the September weather with a walk through town, a visit to one of our parks, or a trip up the mountain to enjoy the view.

Have a great week, Middlesboro!

September is here, and we still have FOUR more nights of live music to enjoy with Levitt AMP Middlesboro! 🎶This Thursday...
09/03/2026

September is here, and we still have FOUR more nights of live music to enjoy with Levitt AMP Middlesboro! 🎶

This Thursday, we’re kicking off the final month of the season with Florencia & The Feeling, with support from Daniel Chumley!

Come downtown, bring a chair, grab something to eat, and enjoy another FREE night of live music in the heart of Middlesboro. And if you haven’t made it to a Levitt concert yet this season, there’s still time!

📅 Thursday, September 3
🎤 Florencia & The Feeling
🎶 Support by Daniel Chumley
📍 Downtown Middlesboro

Four Thursdays. Four concerts. One more month of Levitt AMP Middlesboro.
We’ll see you downtown! 🎵

Today’s fog has us thinking about this beautiful misty view captured from Pinnacle Overlook. There’s something special a...
09/02/2026

Today’s fog has us thinking about this beautiful misty view captured from Pinnacle Overlook. There’s something special about watching the clouds settle between the mountains and transform a familiar landscape into something entirely new.

Even on the grayest days, Middlesboro and the surrounding mountains know how to put on a show. 🌫️⛰️

📜 DID YOU KNOW?The Cumberland Mountain Fall Festival has roots stretching back over 100 years in Middlesboro!As early as...
09/01/2026

📜 DID YOU KNOW?

The Cumberland Mountain Fall Festival has roots stretching back over 100 years in Middlesboro!

As early as 1922, local merchants were organizing a community-wide Fall Festival designed to bring people downtown and showcase the region. Historic editions of the Middlesboro Daily News advertised several days of festivities featuring farm and town products, local merchants, entertainment, contests, exhibits and even poultry shows.

The newspaper called on “the citizenship of the Cumberlands” to come to Middlesboro for the celebration, while downtown businesses filled the special festival edition with advertisements welcoming visitors to town.

Nearly a century later, that same idea still feels familiar: bring people together, celebrate what our region has to offer and support the businesses and community that make Middlesboro home.

🍂 And the timing couldn't be better for this little piece of history...

We are officially ONE MONTH AWAY from the 2026 Cumberland Mountain Fall Festival!

📅 October 2–3, 2026
📍 Downtown Middlesboro

Over the next month, we'll be sharing more about the history of the festival as we get ready to continue a Middlesboro tradition generations in the making.

📅 Middlesboro Moments | August 31 – September 5We’re closing out August and welcoming September in the Magic City! 🍂 Her...
08/31/2026

📅 Middlesboro Moments | August 31 – September 5

We’re closing out August and welcoming September in the Magic City! 🍂 Here’s a look at the week ahead in Middlesboro.

🎶 Levitt AMP Middlesboro
The music continues Thursday night in downtown Middlesboro! Join us for another FREE evening of live music, good food, and community as the Levitt AMP season rolls on.

🏀 Open Gym
Open Gym continues this week at the Middlesboro Community Center! Stop by Tuesday, Wednesday, or Thursday for some time on the court.

📚 School is Back in Session
With our local schools now back in session, remember to slow down, watch for buses, and keep an eye out for students during your morning and afternoon travels. 🚌

🍁 Hello, September!
A new month means we’re getting closer to fall in Middlesboro! Cooler days, changing leaves, and a busy season of community events are just around the corner.

Follow along throughout the week for City updates, local highlights, events, and more from around the Magic City.

Have a great week, Middlesboro! ❤️

🎶 LEVITT NIGHT #6! 🎶Somehow, we’ve already made it to Concert #6 of the Levitt AMP Middlesboro Music Series, which mea...
08/27/2026

🎶 LEVITT NIGHT #6! 🎶

Somehow, we’ve already made it to Concert #6 of the Levitt AMP Middlesboro Music Series, which means we are officially more than halfway through the season!

If you’ve been saying, “I’ll make it to one soon,” consider this your reminder that soon is running out. 😉

Come spend your Thursday evening downtown with FREE live music, good food, and a community that knows how to make a summer night feel pretty special.

📍 Downtown Middlesboro
🎶 D.K. Harrell with support by Billy Crawford & the Lowdown
💲 FREE admission

There are still more Levitt nights ahead, but not nearly as many as there were six weeks ago. Come enjoy them while they’re here!

Address

221 N. 21st Street
Middlesboro, KY
40965

Opening Hours

Monday 8am - 4pm
Tuesday 8am - 4pm
Wednesday 8am - 4pm
Thursday 8am - 4pm
Friday 8am - 4pm

Telephone

+16062485670

Website

Alerts

Be the first to know and let us send you an email when The City of Middlesboro Kentucky posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Shortcuts

Share