The Old Talbott Tavern was built in 1779 in Bardstown, Kentucky.

The Best Small towns in Kentucky To Chill Out

Kentucky, the Bluegrass State, is full of history, culture, and natural beauty. Many visitors come to Kentucky to seek out fun and adventure, but it is also full of great places to simply chill out. If you are one of those visitors looking to just take it easy in Kentucky, check out this list of the towns for chilling out. Whether your idea of relaxation includes shopping at local boutiques in a charming downtown, taking a leisurely nature hike, listening to great live music, or enjoying fine food and drinks, you can be sure of finding an excellent chillout spot in Kentucky.

Bardstown

Roundabout near the historic courthouse and Talbot tavern in Bardstown, Kentucky
Roundabout near the historic courthouse and Talbot tavern in Bardstown, Kentucky.

The seat of Jefferson County in north-central Kentucky, Bardstown, was established in 1780 and named for its founders, the Bard brothers. Bardstown began as a magnet for Roman Catholic settlers—it was home to the first American Catholic diocese established west of the Appalachian Mountains, and its impressive 1823 Basilica of St. Joseph still welcomes worshippers and visitors. Modern Bardstown, however, draws in visitors mainly due to its numerous distilleries, annual Kentucky Bourbon Festival, and self-proclaimed status as the “Bourbon Capital of the World.” If distillery tours, bourbon tastings, and great dining and shopping options in a historic downtown are your recipe for relaxation, Bardstown (population 13,500) is the place for you!

Grand Rivers

Scenic lakeside at Grand Rivers, Kentucky.
Scenic lakeside at Grand Rivers, Kentucky.

The west Kentucky town Grand Rivers was established (and named) for its proximity to the OhioCumberland, and Tennessee Rivers—the damming of the latter two turned the town into an isthmus situated between Kentucky Lake and Lake Barkley. Intended to be a steel-producing center to rival Pittsburgh when founded, Grand Rivers instead remained a small town and is now best known for its surrounding natural beauty, especially the lakes, and rivers. While home to only about 350 residents, Grand Rivers’ status as a gateway to the outdoors means that its inviting downtown area has a range of shops, restaurants, bed and breakfasts, and other businesses that cater to visitors.

La Grange

Ohio Valley Railroad in La Grange, Kentucky.
Ohio Valley Railroad in La Grange, Kentucky. Image credit: NearEMPTiness, via Wikimedia Commons

The seat of Oldham County in northern Kentucky, La Grange, has a charming and historic downtown area, much like many other towns of about 10,000 residents. What is unique about La Grange, however, is that about 25 freight trains per day pass through the heart of downtown on tracks built right into Main Street. Instead of treating this as an annoyance, La Grange has embraced it by housing a railroad museum and catering to visitors who relish the opportunity to see trains up close. But, even if roaring trains are not your cup of tea, remember that La Grange is a quiet, perfectly pleasant town whenever a train is not passing through!

Maysville

Ohio River viewed from Maysville, Kentucky.

Situated on the Ohio River in the northeastern part of the state, Maysville was one of the key passageways for commerce and settlement in early Kentucky. An ancient buffalo trace turned Indian trail became the highway into the bluegrass country of central Kentucky. Maysville also served as an important stop on the Underground Railroad, as escaped slaves fled to freedom across the Ohio River. Now home to about 9,000 residents and situated on hills overlooking the river, Maysville is a picturesque community with a delightful mix of historic sites and local businesses. It is a great place to relax on the river, soak up some history, or do some boutique shopping.

Murray

Monument honoring the Confederate soldiers on the northeast corner of the Murray court square
Monument honoring the Confederate soldiers on the northeast corner of the Murray court square.

As the seat of Callaway County in southwestern Kentucky and the home of Murray State University, the town of Murray can feel bigger than its population of a little over 17,000. But Murray was also once named the “friendliest town in America” by Rand McNally and USA Today. A nice mix of college town vibe and small southern town atmosphere makes Murray an inviting place to explore. Along with an art museum and history museum, Murray houses numerous historic markers and sites, including a controversial Confederate monument at the courthouse complex. But Murray is generally a town where all can feel welcome to take a stroll or just sit back and relax.

Paducah

Historic buildings in the downtown district of Paducah, Kentucky.
Historic buildings in the downtown district of Paducah, Kentucky. Editorial credit: Angela N Perryman / Shutterstock.com

Paducah was laid out in 1827 by famed western explorer William Clark at the confluence of the Ohio and Tennessee Rivers in far western Kentucky, about halfway between St. Louis and Nashville. More recently, Paducah was named a UNESCO Creative City in 2013 for its contributions to cultural connections through creativity. Paducah is proud of its reputation as a welcoming and creative community of about 27,500 and has also done an admirable job preserving its past. A 20-block section of downtown is designated as a historic district, and the entire downtown area is great for shopping or just sightseeing. Paducah’s location along two major rivers also provides ample options for outdoor recreation.

Somerset

Golf course at General Burnside State Park
Golf course at General Burnside State Park in Somerset, Kentucky. Editorial credit: ehrlif / Shutterstock.com

The south-central Kentucky town of Somerset, population 12,000, has a pleasant downtown area with historic buildings and a nice range of businesses, but many visitors come for attractions just outside of town. The Civil War battle of Mill Springs was fought about 8 miles west of town in 1862, and a museum and visitors center now exists at the site. Additionally, Somerset is located in close proximity to both Lake Cumberland and the Daniel Boone National Forest, which are significant outdoor recreation draws. Yet it is definitely worthwhile to spend some time in town as well, especially for events like the Master Musicians’ Festival and “Somernites Cruise” car show (Kentucky’s largest).

Thinking about Kentucky brings to mind things like bluegrass music, thoroughbred horses, and bourbon whiskey. And if you are someone who loves any or all of those things, Kentucky is definitely a great place to visit. But even if your idea of chilling out is more along the lines of a canoe trip or shopping for antiques, the commonwealth of Kentucky has plenty of towns, both small and really small, that can help you relax and recharge.

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