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Discover Kentucky’s Most Charming Towns!

Owensboro High Street, Owensboro, Kentucky

Beyond the famous bourbon trails and Kentucky Derby excitement lies a collection of enchanting small towns, each with its own unique character and stories to tell. From historic river ports to college towns steeped in tradition, these Kentucky gems offer visitors an authentic slice of Bluegrass State charm.

Each one of the following small towns is only a day trip from one of the major cities in Kentucky like Louisville or Lexington, but it’s imbued with its own identity, food and folklore. I wasn’t prepared to learn so much about my birth nation’s history and meet those who have made the world better from their home base of Kentucky.

Covington

Mainstrasse, Covington, Kentucky
Image Credit: MeetNKY

Positioned along the Ohio River with stunning views of Cincinnati’s skyline, Covington blends German-American heritage with modern urban vibrancy in its historic MainStrasse Village. The city’s stunning Cathedral Basilica of the Assumption, modeled after Notre-Dame in Paris, features one of the world’s largest stained-glass windows.

Covington’s thriving arts district, anchored by the Artisan Enterprise Center, showcases local talent while trendy restaurants and craft breweries like Braxton Brewing Company have transformed the once-industrial Pike Street corridor into a culinary destination.

For a wonderful stay in Covington and Newport, I loved the Hotel Covington, the chicest place in town with the longest bar.

Newport

Gangster Tour, Newport, Kentucky
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Newport can be described in one phrase – Vegas before there was a Vegas. It’s hard to imagine that one of the small towns in Kentucky as the gambling capital of the USA. Our guide on the Newport Gangster Tour assures us it was.  At the height of its popularity, there were more than 30 illegal casinos within the confines of a few blocks. Frank Sinatra sang here – need I say more?

Prohibition just fueled the fury and, thanks to the Ohio River situated steps away, bootleggers could smuggle in goods with help from the easily-bribed town officials! The original Flamingo and Tropicana casinos originated right here in town. The fun ended in 1963 when the Feds arrived and shut down all the casinos. Air travel replaced rail and Las Vegas became what it is today.

Burlington

Fried Chicken, Burlington, Kentucky
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Wherever you are driving next on your tour through the small towns of Kentucky, do not miss lunch at Tousey House Tavern in Burlington. Their fried chicken is considered some of the best in the state. Not only is the food spectacular, but the building itself is a prime example of Federalist architecture built in 1822. Burlington, also known as Porkopolis to locals, due to its historic German immigrant population. They brought their wurst and stayed.

Don’t be scared to try Goetta from the menu. If you are a Pennsylvanian, you’ll know its closest relative, Scrapple. If not, let’s just say, it’s a melange of pork, oats, and spices, mashed up, steamed and then fried. If more fried food is what you’re after, don’t miss their Fried Green Tomatoes.

Georgetown

Heading into Old Friends, Georgetown, Kentucky
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It may be tiny, but Georgetown is a must stop on any trip through the small towns in Kentucky. The historic centre of Georgetown includes over 200 buildings on the National register of Historic Places. Most of the shops are locally owned with nary a chain store to be seen.  Elijah Craig (of Bourbon fame) was the founder of the town, so you know you will drink, and eat, well

Right outside of Georgetown, you are in the Horse Capital of the World and there are two farms that just can’t be missed. Old Friends Farm for Retired Thoroughbreds is my kind of heaven. Over the past 15 years, Michael Blowen, former Film Critic of the Boston Globe, has been saving former thoroughbreds from being destroyed.

In Georgetown, there is a myriad of chain properties the most luxurious in town is the Country Inn & Suites by Radisson.

Owensboro

Bluegrass Hall of Fame in one of the small towns in Kentucky, Owensboro
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Time for twanging. The sound that is so iconic in country music was born in a little green and white clapboard house outside of Owensboro, Kentucky. The fast-flying fiddle, high pitched mandolin, free-flowing 5-string banjo, bass and guitar are the only ingredients allowed if you are making traditional Bluegrass Music, according to its founder Bill Monroe. The genre came to be named for his band, Bill Monroe and the Blue Grass Boys, and took off from his very first concert at the Grand Ole Opry in Nashville.

The same day you visit Bill Monroe’s birthplace, it would be a shame to miss Owensboro, the home of the Bluegrass Hall of Fame and Museum. The Museum has just opened its new premises, making it the most comprehensive museum of the genre that started country music as we know it today. Don’t just visit the museum, but take a long walk on the riverfront and gaze cross the Ohio River to Indiana.

In Owensboro, the best is the Hampton Inn and make sure to ask for a river view.

Check out more charming towns in the USA

3. Bar Harbor, Maine
Image Credit: Carlos/Adobe Stock

The United States is a vast country filled with stunning landscapes, rich histories, and charming towns that offer picturesque views, captivating architecture, and warm hospitality. If you’re looking to escape the hustle and bustle of big cities, these small towns are perfect destinations. From coastal gems to mountain retreats, here’s a list of the 20 prettiest towns in the USA that will leave you awe-inspired.

Find the list here

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