The state of Kentucky is made up of mostly small towns, each with their own charm and appeal. Our state is diverse in landscape and also in its little towns that are the heart beat of the Bluegrass State. While each town is special, these 11 Kentucky cities stand out thanks to being small in size, but truly big in character. Each one offers something unique and is also much loved by those who live there and those who visit, making these towns just some of the treasures of our delightful Kentucky.
- Midway
Facebook/Midway, Kentucky When you enter the town of Midway, and turn on the small road that leads through downtown, prepare for it to take your breath away. This enchanting little town has a nostalgic railway that runs right through it, which is also lined with shops and restaurants. The town is idyllic and its residents know how lucky they are to call this character-filled city home.
- Rabbit Hash
Facebook/Rabbit Hash General Store This tiny Kentucky town is so filled with character that it just can’t be deterred. Rabbit Hash centers around its famous, historic General Store, which sadly suffered a devastating fire in 2016. The town and those who love it rallied together and rebuilt this classic Kentucky landmark. It’s definitely a small town, with a very big heart.
- Ashland
Flickr/Don Johnson 395 Ashland is a beautiful small town, nestled along the banks of the Ohio River in Northeast Kentucky. The city is filled with character, charm, history and passionate local residents who love their town dearly. The peculiar picture above represents a get together of “The Hillbillies,” a group of Shriners (a fraternity of sorts) who work hard to raise money for Shriners Hospitals for Children. It is in no way meant to put down this lovely town, but rather to focus on the vibrancy and comradery of Ashland.
- Owensboro
Flickr/Jimmy Emerson, DVM Owensboro, often referred to as the Bar-B-Q Capital of the World, is another small Kentucky town that is oozing character. The city is actually the industrial, medical, retail and cultural hub of western Kentucky and with its location along the Ohio River, it’s a picturesque spot to visit. Check out the impressive Smothers Park, one of the many festivals throughout the year, and of course, don’t forget to try the bar-b-q.
- Pineville
Flickr/James Carnes Pineville is a hidden gem, tucked away in the valley of Pine Mountain. The town hosts Kentucky’s longest running festival, the Kentucky Mountain Laurel Festival, which will take you back in time and also showcases the beauty of this city and its residents.
- Pikeville
Facebook/Pikeville Hillbilly Days Not to be confused with Pineville, Pikeville is also an Eastern Kentucky town that is filled with character. They host one of the most unique festivals in the state - Hillbilly Days - and they also work hard to preserve the history and character of the city. Pikeville has strong ties to the famous Hatfield McCoy Feud and also is ideal for enjoying outdoor adventure of all kinds.
- Benton
Facebook/Classy and Grassy Blink and you may miss this tiny town, unless of course you’re visiting during Tater Day! This famous festival started all the way back in 1843 and remains a festive time in Benton today. The town has maintained a laid back, nostalgic appearance with charming restaurants and plenty of down home appeal.
- Paducah
Facebook/Paducah Creative City Paducah is a haven for those who wish to express creativity in a variety of ways. This riverside town has enough character to fill a big city and enough to keep you busy and entertained to warrant a day trip.
- Shelbyville
Facebook/Bell House Restaurant Shelbyville is a lovely mix of small town charm and rural horse country and residents are passionate about helping to maintain its character. The town has many longstanding restaurants and businesses and also has moved with the times, boasting cool coffee shops and loft apartments.
- Elkhorn City
Flickr/C Hanchey Elkhorn City is an outdoor adventurer’s dream and the town is filled with natural beauty and character. Try whitewater rafting and hike to incredible views all near this Kentucky Trail Town, which is very passionate about maintaining its rustic quality.
- Maysville
AJP Drones Maysville is one of the most delightful river towns in Kentucky, with unique architecture and plenty of history. There are bustling shops, outdoor activities, and friendly people waiting to greet you and show you the true character of this Kentucky town.
The entire state of Kentucky is big in character, so it comes as no surprise that our small towns would be the same exact way. What do you think of these character filled towns? What others would you add to the list? Let us know in the comments!
Facebook/Midway, Kentucky
When you enter the town of Midway, and turn on the small road that leads through downtown, prepare for it to take your breath away. This enchanting little town has a nostalgic railway that runs right through it, which is also lined with shops and restaurants. The town is idyllic and its residents know how lucky they are to call this character-filled city home.
Facebook/Rabbit Hash General Store
This tiny Kentucky town is so filled with character that it just can’t be deterred. Rabbit Hash centers around its famous, historic General Store, which sadly suffered a devastating fire in 2016. The town and those who love it rallied together and rebuilt this classic Kentucky landmark. It’s definitely a small town, with a very big heart.
Flickr/Don Johnson 395
Ashland is a beautiful small town, nestled along the banks of the Ohio River in Northeast Kentucky. The city is filled with character, charm, history and passionate local residents who love their town dearly. The peculiar picture above represents a get together of “The Hillbillies,” a group of Shriners (a fraternity of sorts) who work hard to raise money for Shriners Hospitals for Children. It is in no way meant to put down this lovely town, but rather to focus on the vibrancy and comradery of Ashland.
Flickr/Jimmy Emerson, DVM
Owensboro, often referred to as the Bar-B-Q Capital of the World, is another small Kentucky town that is oozing character. The city is actually the industrial, medical, retail and cultural hub of western Kentucky and with its location along the Ohio River, it’s a picturesque spot to visit. Check out the impressive Smothers Park, one of the many festivals throughout the year, and of course, don’t forget to try the bar-b-q.
Flickr/James Carnes
Pineville is a hidden gem, tucked away in the valley of Pine Mountain. The town hosts Kentucky’s longest running festival, the Kentucky Mountain Laurel Festival, which will take you back in time and also showcases the beauty of this city and its residents.
Facebook/Pikeville Hillbilly Days
Not to be confused with Pineville, Pikeville is also an Eastern Kentucky town that is filled with character. They host one of the most unique festivals in the state - Hillbilly Days - and they also work hard to preserve the history and character of the city. Pikeville has strong ties to the famous Hatfield McCoy Feud and also is ideal for enjoying outdoor adventure of all kinds.
Facebook/Classy and Grassy
Blink and you may miss this tiny town, unless of course you’re visiting during Tater Day! This famous festival started all the way back in 1843 and remains a festive time in Benton today. The town has maintained a laid back, nostalgic appearance with charming restaurants and plenty of down home appeal.
Facebook/Paducah Creative City
Paducah is a haven for those who wish to express creativity in a variety of ways. This riverside town has enough character to fill a big city and enough to keep you busy and entertained to warrant a day trip.
Facebook/Bell House Restaurant
Shelbyville is a lovely mix of small town charm and rural horse country and residents are passionate about helping to maintain its character. The town has many longstanding restaurants and businesses and also has moved with the times, boasting cool coffee shops and loft apartments.
Flickr/C Hanchey
Elkhorn City is an outdoor adventurer’s dream and the town is filled with natural beauty and character. Try whitewater rafting and hike to incredible views all near this Kentucky Trail Town, which is very passionate about maintaining its rustic quality.
AJP Drones
Maysville is one of the most delightful river towns in Kentucky, with unique architecture and plenty of history. There are bustling shops, outdoor activities, and friendly people waiting to greet you and show you the true character of this Kentucky town.
And for more small towns in Kentucky, check out these historic spots from a previous article here.
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