The Best Small Towns in Kentucky

While a day at the races or an elegant show in the Louisville Theatre can be nice, sometimes you need a day to get out of the city and explore the countryside. We're here to help you plan the best day trip out to some of the coolest small towns in Bluegrass nation.

Because the towns you'll be able to visit will largely depend on where you choose to stay, we've highlighted which bed and breakfasts are closest to each one. Get ready for our tour around Kentucky!

Bardstown, KY

Just a short drive out of Louisville lies the thriving metropolis of Bardstown. This tiny town is a beacon of history for guests who want to learn about all aspects of the Bluegrass State.

My Old Kentucky Home Museum

Get a taste for what life was like in the early 20th century. The Old Kentucky Home State Park offers tours of a historic mansion from the era. On top of that, you can play a round of golf or walk the grounds to learn more about the area. The Stephen Foster Story plays during the summer.

Oscar Getz Museum of Whiskey History

Whiskey has a crucial part in Kentucky history, as is obvious from the Bourbon Trail and the many smaller breweries around the state. However, an oft-overlooked attraction is the museum of whiskey history, that tells the stories of the historical figures of Whiskeyland.

Civil War Sites

Kentucky was in an interesting place during the Civil War. Learn the story of the Civil War with real artifacts and accounts at the Old Bardstown Village. The sobering stories about the war make for an interesting way to share history with children.

We often hear of the casualties men suffered when fighting in the war, but what about the women? You can learn more about their experiences and challenges during wartime as well at the Women's Civil War Museum.

Nearby Bed and Breakfasts

*Red Rose Inn - In Bardstown
*Bourbon Manor Bed and Breakfast - In Bardstown
Maple Hill Manor
Louisville Bourbon Inn

Berea, KY

Berea is about an hour south of Lexington and is a bit of a "variety pack" of activities. Makes for a fun experience no matter where your interests lie.

Outdoor Activities

For outdoorsmen, you have quite a few options! You can ride, jog, or walk on the Boone Trace Nature Trail—a favorite walking trail for many people. Guests who are more interested in hunting and fishing might want to hit up the Central Kentucky Wildlife Management Area to schedule a hunting expedition. Make sure you bring your license!


Want more Civil War history? You got it! Battlefield Park is the site of one of the most brutal battles of the Civil War in Kentucky—the Battle of Richmond. The Civil War Buffs here will be able to tell you how the battle went, answer your questions, and paint the picture for everyone visiting.

Kentucky Artisan Center isn't your typical museum, but is instead a collection of handmade items created by local artisans. If you need the perfect souvenir stop, this would be it!

Nearby Bed and Breakfasts

The Denny House
Charred Oaks Inn
The Blue Heron Bed and Breakfast and Retreat
Rosecrest Farm
Lyndon House Bed and Breakfast
Eighth Pole Inn

Cave City, KY

Cave City lies a stone's throw away from Mammoth Cave National Park, and while the national park might be the reason you're staying near Cave City in the first place, you should still check out the local attractions here.

Crystal Onyx Cave

For one, there is a smaller cave that offers a pretty fascinating look at subterranean formations here at the Onyx Cave. It's well lit and more straightforward compared to some of the tours in the national park, so it might be worth a visit if you have young kids or can't move as well as you used to.

Dinosaur World

RAWR! The Dinosaurs are running amok in Kentucky, and it's your job to find them! That's at least what you can tell the kiddos when you come to the funnest park in the state—Dinosaur World.

With large replicas of different beasts from an ancient day, Dinosaur World is fun for the whole family. There are also other fun activities for children to love, including fossil digging.

Nearby Bed and Breakfasts

Grand Victorian Inn
Main Street B&B
Ivy Manor Bed and Breakfast
L&N Bed and Breakfast

Owensboro, KY

Owensboro is probably the most remote town from any of our bed and breakfasts, which is a shame because it has a lot to offer! Take a look at the downtown area if you ever decide to go.

RiverPark Center

The RiverPark Center is a historic theater in the downtown area where you can listen to singers, watch plays, and see all manner of different performances! Take a look at the calendar and plan your trip.

Western Kentucky Botanical Garden

Enjoy a slice of the natural world at this beautiful botanical garden. You'll have the chance to walk through rooms full of flowers native to the south. Events are held throughout the year, using the butterflies and flowers as a backdrop for fun activities.

Bluegrass Music Hall of Fame and Museum

We've talked about Kentucky's food, booze, and horse culture tons of times, but not yet music! That's a shame, because Kentucky is known for being the birthplace of bluegrass. Learn some of the history of the sound, find a concert playing nearby, and appreciate the noises of Kentucky.

Nearby Bed and Breakfasts

Southern Grace Bed and Breakfast

Check Out Our Travel Guide!

Looking for more things to do throughout the Bluegrass State? Check out our useful travel guide, where we cover everything from Covington to Paducah, KY. Want to tour a horse farm in Lexington? Need to plan a vacation to downtown Louisville? We can help you here!