The Kentucky River flowing through Frankfort, Kentucky.

The Best Small Towns In Kentucky For A Weekend Retreat

The origin of Kentucky’s name is often in contention. Did it come from the Shawnee word "Kain-tuck-ee" for "At the Head Of The River"? The Wyandot or Huron word "Kah-ten-tah-teh," meaning "Fair Land of Tomorrow”? Or words for “meadows” and “prairies” deriving from the Mohawks, Delawares, and Catawbas? Whatever the case, what is not in contention is the best small towns in Kentucky that are perfect for a weekend retreat.

From historic hometowns like Hodgenville to capitals of art and industry such as Bardstown and Berea, these towns are sure to satisfy your curiosity like a Kentucky Fried Chicken satisfying your tastebuds. Let the Appalachian Mountains give you a good backdrop as you roam through the horse-filled meadows and prairies of Kentucky.

Bardstown

Town Square of Bardstown, Kentucky.
Town Square of Bardstown, Kentucky. Editorial credit: woodsnorthphoto / Shutterstock.com.

Travel an hour from Louisville and let yourself be serenaded by Bardstown, the Bourbon Capital of the World. There, you can sample all manner of bourbon from 11 unique distilleries and can even savor more during the Kentucky Bourbon Festival in September. There are even historic bourbons to be admired at the Oscar Getz Museum of Whiskey History and the Barton 1792 Distillery & Visitor Center, the latter being the oldest operating distillery in Bardstown.

Bring your well-bought and distilled bourbon with you at the Stephen Foster Story, a Broadway-themed performance chronicling Stephen Collins Foster, an American composer. Outside the human-made beauties, you can enjoy the craftsmanship of nature at the Bernheim Arboretum and Research Forest. Places that sell fine spirits are not without equally excellent lodgings, and Bardstown certainly has a handful of establishments like the Old Bardstown Inn, the Fairfield by Marriot Bardstown, and Bourbon Manor Bed & Breakfast.

Berea

Scenic aerial view of Central Kentucky countryside near Berea
Scenic aerial view of Central Kentucky countryside near Berea.

Hailed as “the Folk Art & Crafts Capital of Kentucky,” Berea is where you go when you want to find the best craft galleries, gift shops, and artisan studios along the Kentucky River. Berea is also a perfect starting location to travel down the Boone Trace—a historic trail that meanders through the Cumberland Gap and connects Berea to Middlesboro and Pineville northward. A pioneer named Daniel Boone discovered an old trail that buffalo herds and Native Americans traversed and improved upon it for modern traversal.

This new trace also gives visitors access to the Rockcastle River and Boonesborough, both located on the Kentucky River’s south bank in the outer Bluegrass Region. Adjacent to the Boone Trace is the Daniel Boone National Forest, where The Pinnacles in the Berea College Forest offer a great view of Berea. In the town itself, the Historic Boone Tavern Hotel and Red Roof Inn are some of the best lodgings you can spend the night at.

Paducah

Maiden Alley in the downtown arts district of Paducah, Kentucky.
Maiden Alley in the downtown arts district of Paducah, Kentucky. Editorial credit: Wendy van Overstreet / Shutterstock.com.

Paducah, situated on the banks of the Ohio River, is one of the few cities bestowed the illustrious title of a UNESCO Creative City. For years, the town has been a locus for literary and cultural expressions in a plethora of fields and media. The National Quilt Museum, for example, contains many advanced quilting techniques and award-winning quilts that will stun and amaze anyone. Robert Dafford’s Paducah "Wall to Wall" Murals showcase fifty painted panels, each as unique as the next and showcasing Paducah’s dynamic and magnificent past.

Every year in mid-April, one can witness the annual Dogwood Trail Celebration to see the surrounding dogwood trees blossom into full bloom. For those of you who wish to explore more of Paducah’s creativity, remember to book a room at either the Candlewood Suites or Baymont Inn.

Danville

Boyle County Courthouse in Danville, Kentucky
Boyle County Courthouse in Danville, Kentucky.

Travel down the Dix River into Herrington Lake and settle down in the village of Danville. Popularly known as “The City of Firsts,” Danville was where the first Courthouse in Kentucky was built in 1785. Later, in 1792, the first US Post Office west of the Alleghenies and the first Constitutional Convention to create the Bluegrass region were established in Danville.

Finally, in 1809, Dr. Ephraim McDowell became the first physician in the world to successfully remove an ovarian tumor. About 10 miles west of Danville is the site of the Perryville Battlefield, Kentucky’s bloodiest American Civil War battle that took place in October 8, 1862. Nearby, visitors can go back in time at the Shaker Village of Pleasant Hill, the third largest Shaker community in the US. In this city of firsts, be among the first to book a room at the Hampton Inn Danville, Comfort Suites, or Quality Inn.

Harrodsburg

Beautiful Downtown Harrodsburg, Kentucky
Beautiful Downtown Harrodsburg, Kentucky. Image credit: J. Stephen Conn via Flickr.com.

Harrodsburg, approximately 10 miles from Danville, is a lovely town that charms visitors with its Victorian architecture and English atmosphere. As a former pioneer settlement, Harrodsburg is the oldest English settlement west of the Alleghenies. In the Old Fort Harrod State Park, visitors can stay at a replica of an old fort that frontiersman Daniel Boone used to stay in. In addition, you can find the George Rogers Clark Memorial and the Lincoln Marriage Temple, the latter being the site where Abraham Lincoln’s parents got married.

Since Harrodsburg is close to Danville, you can also take a detour to the nearby Shaker Village of Pleasant Hill or visit other historic settlements and structures like the Morgan Row Houses and the Old Mud Meeting House of the Dutch Reformed Church. For those eager to spend their evenings in Harrodsburg, the Clarion Pointe Harrodsburg-Danville and the Beaumont Inn have the amenities you need to enjoy your weekend in town.

Greenville

A historical building in Greenville, Kentucky
A historical building in Greenville, Kentucky. Editorial credit: Sabrina Janelle Gordon / Shutterstock.com.

Deemed the safest urban area in Kentucky, you need not feel worried or anxious in the hillside village of Greenville. The Brizendine Brothers Nature Park is a 12-acre woodland filled with many of Kentucky’s flora and fauna, all of which are protected by a woodwork sculpture of Yogi the bear. Close to the park is Lake Malone, an excellent spot for kayaking and fishing unless you wish to take the Laurel Trail or Wildflower Trail to scenic walks along the shore. At the Muhlenberg County Park, you can partake in several sports facilities to optimize daily exercises.

And you can always pay tribute to the fallen at the 9/11 Memorial, where you can find a 17-foot box beam that fell from the North Tower of the World Trade Center. Only two hours away from Nashville, seek your accommodations at either The Wickliffe House or the Convention Center Inn (CCI Express Inn).

Glasgow

South Green Street in Glasgow, Kentucky.
South Green Street in Glasgow, Kentucky. Image credit: Ichabod via Wikimedia Commons.

Founded by Scottish pioneer John Matthews, the town of Glasgow was named after the city of Glasgow in Scotland. Several American Civil War skirmishes occurred in the surrounding area, and many of the martial relics and remnants remain. Fort Williams, for example, was once a Union fortress that withstood John Hunt Morgan and his raiding armies. Today, visitors can explore the ruins of this formidable fort to understand Glasgow’s strategic significance in Kentucky.

Besides warfare, Glasgow is renowned for its access to the Mammoth Cave National Park, both an International Biosphere Reserve and a UNESCO World Heritage Site. Adjacent to this cave is the Prehistoric Jewel Site Complex, a home to many Native American tools and weapons for early hunters. There is more to see in Glasgow, and if you wish to spend your days in this Scottish town, then you might want to stay a while in the 1852 Hall Place Bed & Breakfast, where Abraham Lincoln once dined.

Frankfort

The Kentucky River flowing through Frankfort, Kentucky.
The Kentucky River flowing through Frankfort, Kentucky.

Located in one of the many fords on the Kentucky River, “Frank’s Ford,” or Frankfort, is one of the biggest trading hubs in the Bluegrass region. The Thomas D. Clark Center for Kentucky History highlights Frankfort’s significance during the American Civil War. Several 18th and 19th-century structures represent the different architectural formats of various periods. For example, Liberty Hall is a Georgian mansion built by John Brown. Within Liberty Hall is the Orlando Brown House, built by Gideon, who also designed the Old State Capitol building.

At the Frankfort Cemetery, you can find the graves of legendary trailblazer Daniel Boone and his wife, Rebecca. You might find the place where Rebecca Gooch and Ruth Hanly Booe created the renowned Kentucky Bourbon Ball. Only halfway between Louisville and Lexington, come see the majesties of Frankfort by first booking a room at either the Capital Plaza Hotel or Bluegrass Inn.

Hodgenville

Abraham Lincoln Memorial in Hodgenville, Kentucky
Abraham Lincoln Memorial in Hodgenville, Kentucky.

America would not be as it is without Abraham Lincoln, and Abraham Lincoln would not be the man he was without Hodgenville. Only about 12 miles from Elizabethtown and situated at the North Fork of the Nolin River, Hodgenville is where young Lincoln spent much of his youth prior to his family's relocation to Indiana. The Abraham Lincoln Birthplace National Historic Site illustrates Lincoln’s childhood, while the Old Sinking Spring Farm was the original farm where Lincoln was born.

Nearby, the Knob Creek Farm was where Lincoln’s family moved when he was two years of age, and Salem Lake and Pearman Forest were arboreal paradises where the great president fulfilled much of his fun time and which you can do as well. To enhance the Lincoln-themed setup of Hodgenville, the town has its own Lincoln Lodge to serve as an impeccable lodging for you to spend your evenings.

Maysville

Maysville, Kentucky.
Maysville skyline showing the Mason County courthouse and the Simon Kenton Memorial Bridge over the Ohio River. Image credit: Nealparr via Wikimedia Commons.

On the banks of the Ohio River, just an hour away from Lexington, Kentucky, and Cincinnati, Ohio, is the gorgeous town of Maysville. To reach this laidback town, one can traverse the covered bridges called “Timbered Tunnels,” which connect Maysville to Aberdeen, Ohio, and other nearby communities. You can marvel at the region's local history at the Kentucky Gateway Museum Center. Furthermore, you can gaze at the museum's award-winning dioramas and around 4,000 regional artifacts.

Visitors might come across a mural of The Underground Railroad, a testament to how enslaved African-Americans found freedom during the Civil War. The Underground Railroad also honors Reverend John Rankin, an abolitionist and stationmaster conductor of the actual Underground Railroad. You can find his house along the Ohio River. To those who are eager to see more of Maysville, do not forget to find accommodations first at the Hampton Inn, French Quarter Inn, or Lee House Inn.

In a state renowned for giving the world KFC, Kentucky has much more to offer in “The Fair Land of Tomorrow.” Whether watching the Kentucky Derby in Louisville or listening to Bluegrass music in the Bluegrass region, you should not forget to visit the best small towns in Kentucky for a weekend retreat. Buy yourself a bucket of KFC while touring the living histories of Mayville, delving into the caves of Glasgow, and enjoying the freedoms and liberties of Greenville. Be the first to visit the City of Firsts in Danville and savor the bourbon in Bardstown or admire the artworks of Berea. Wherever you go, grab a snack of KFC on your grand journey.

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