In Kentucky, Small Cities Leave a Big Impression. Here Are 5 to Visit.

This trip through small-town Kentucky explores the cultural legacy of the state’s early settlers, which can be felt like a strong heartbeat in compact cities that do, indeed, offer big experiences.

Berea

Things to do in Berea

Berea College

We arrived in Berea from Blue Grass Airport in Lexington shortly before 8 PM. The drive took slightly less than an hour. Our itinerary had us leaving Berea the next morning at 8:30 AM, so our visit was limited. Most shops and sites were closed when we got there and when we left.

Known as the “Crafts Capital of Kentucky,” Berea (pop. 16,129) was named after a biblical town and founded by folks sympathetic to emancipation and abolition. Berea was incorporated in 1890, but the area’s history was highly influenced by the founding of Berea College in 1855.

Unlike any other college, Berea College was the first integrated, co-educational college in the South and has not charged student tuition since 1892. A private liberal arts work college, Berea College continues a tradition of requiring all students to work 10 to 20 hours in different jobs around the campus to pay for textbooks and room and board. Berea College has 1,600 students, mostly from Appalachia but also from around the world.

Berea College: 101 Chestnut St, Berea, KY 40403

Where to eat and drink in Berea

Boone Tavern Restaurant

Stepping into the Historic Boone Tavern Hotel and Restaurant, we stashed our luggage at the front desk and headed straight to the restaurant since it was almost closing time. The smell of the tavern’s legendary spoonbread let us know this was going to be a memorable meal.

Founded in 1909 and named in honor of frontiersman Daniel Boone, the tavern is owned by Berea College and has long been a favorite on Berea’s College Square. The menu has plenty to tempt any palate. My choice was the comforting chicken flakes — creamed chicken served in a crisp potato nest with mashed potatoes, green beans, and cranberry-orange relish. Boone Tavern also serves alcoholic beverages — a wide list of them, in fact, since 2014.

But what makes dining at Boone Tavern particularly special is that every lunch and dinner starts with a complimentary serving of the restaurant’s famous spoonbread. The creamy, pudding-like dish got its name because it’s served with a spoon and usually topped with a dollop of butter, honey, or sorghum. If you want to serve it at home, the recipe is below.

Before heading out the next morning, we enjoyed an early breakfast in Boone Tavern. Buttermilk biscuits, pork sausage gravy, and sunny-side-up eggs for me. Other diners said the chia pudding was great: coconut milk, honey, house-made granola, muffin, fresh berries, or banana.

Boone Tavern Restaurant: 100 Main St., Berea, KY 40403

Where to stay in Berea

Historic Boone Tavern Hotel

The story goes that in 1908, Eleanor Frost — wife of Berea College President William Goodell Frost — hosted 300 overnight guests in the president’s home and served meals to 1,500 people. Not surprisingly, that’s when Eleanor Frost decided the college needed a hotel.

In those days, electric lighting and indoor bathrooms were not common. But the new Boone Tavern Hotel that opened in 1909 had the newfangled electricity in its 25 guest rooms. Before long, the hotel expanded to a third floor and added indoor bathrooms in 1915. Over the years, the smoke-free Boone Tavern Hotel grew to 63 guest rooms, a cafe, a restaurant, and a reputation as one of the finest small inns in the South.

Checking into my overnight room, the friendly desk clerk handed me a metal key instead of the customary plastic key card used by most hotels, and I could see why Boone Tavern Hotel has so many return guests. Reminding me of my grandmother’s Kentucky farmhouse guestroom, my room had lovely handcrafted wooden beds, a dresser, a desk, and a chair. The bathroom was large with a walk-in shower plus plenty of hot water and good water pressure.

Historic Boone Tavern Hotel: 100 Main St., Berea, KY 40403

Stearns

Things to do in Stearns

Big South Fork Scenic Railway

About 90 minutes from Berea is the little town of Stearns (pop. 1,222) where we boarded the Big South Fork Scenic Railway for a 45-minute train ride to the former coal town of Blue Heron. The clackety train with its six passenger cars passed through beautiful wilderness where we could look outside of our open train window to see wandering streams and steep-walled canyons.

Now an outdoor museum managed by the National Park Service, Blue Heron was once a busy coal mining camp. From 1937 to 1962, hundreds of people lived and worked in this isolated community on the banks of the Big South Fork River.

After extracting most of the coal and timber, the Stearns Coal and Lumber Company pulled out. Without work, most people moved away, too. What immediately caught my eye when we first arrived was the huge coal tipple and the railroad bridge across the river. The tipple is where coal cars brought the coal to be sorted. Views from the bridge are well worth the walk.

In 1989, most of the original buildings were ingeniously rebuilt as “ghost structures.” The 16 steel skeletons of former buildings include life-size photographs of miners and their families, plus taped interviews of former Blue Heron residents.

It was a bit eerie and sad to hear past residents talk about the difficult life in a coal camp. Each ghost structure deals with a particular aspect of Blue Heron life, such as school, church, and women’s life. Few children finished school beyond the eighth grade. Some only went until they were old enough to work. In the tape recording, one full-grown man noted that he regretted not having more education, so he asked the teacher if he could return and learn. She agreed. The older man sat with fourth-grade students. And he learned.

Big South Fork Scenic Railway: 66 Henderson St., Stearns, KY 42647

Where to eat and drink in Stearns

Whistle Stop

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Finding a place to eat in Stearns was simple. We got off our train ride on the Big South Fork Scenic Railway, walked into the train depot, and sat down at the Whistle Stop cafe. The place was hopping with hungry diners, but we were quickly waited on by an efficient waitress.

My fried chicken sandwich was okay, as were the onion rings. But I was already pretty full from the beer cheese and pretzel appetizer. I was surprised to learn that a small Kentucky town I’d be visiting is known as the Beer Cheese Capital of the world. More about that later.

Whistle Stop: 66 Henderson St., Stearns, KY 42647

Corbin

Things to do in Corbin

Colonel Harland Sanders Park

A 50-minute drive from Stearns brought us to Corbin where we spent the rest of the day and night. A very sweet, walkable little town (pop. 7,843), Corbin is home to Colonel Harland Sanders’ original Kentucky Fried Chicken restaurant. Although Sanders died of leukemia on December 16, 1980, at age 90, his image is still very much alive in Corbin.

Dedicated in 2015, Sanders Park honors Corbin’s famous son. Located on the main shopping street, Sanders Park features a life-size bronze statue of Sanders as well as a Secret Recipe Garden containing some of the 11 herbs and spices used in Sanders’ famous, secret, finger-licking-good recipe.

Before his death, Sanders gave millions to hospitals, schools, and charities. “There’s no reason to be the richest man in the cemetery. You can’t do any business from there,” Sanders is quoted on a park plaque.

Sanders Park:201 S. Main St., Corbin, KY 40701

Pinball Museum of Corbin

Bells ring. Lights flash. Queen’s Freddie Mercury belts a tune as Elton John adds his music from a nearby machine. Floating over the room is oldies-but-goodies songs, primarily from the 1970s and 1980s. The Pinball Museum of Corbin is definitely entertaining. And different.

This museum doesn’t have “Don’t Touch” rules. In fact, visitors of all ages are invited to play the more than 100 pinball machines, 10 arcade cabinets, two big ball bowlers, and some newer machines that reward gamers with prizes. Machines date from 1969 to 2024, including the world’s largest pinball machine: the 1977 Hercules made by Atari.

You don’t need a pocketful of quarters to play pinball here, either. A single $18 entrance fee allows customers to play the machines all day. Prepare to be pinball pampered with these games – Super Mario Bros, The Godfather, Wrestle Mania, The Sopranos, The Addams Family, Transformers, Aerosmith, The Beatles, Jurassic Park, Halloween, The Wizard of Oz, and many more. My favorite? John Wick.

Pinball Museum of Corbin: 112 S. Main St., Corbin, KY 40701

Cumberland Falls

Called the “Niagara of the South,” Cumberland Falls forms a 125-foot-wide curtain that plunges almost 70 feet into the boulder-strewn gorge below. On clear nights under a full moon, when the wind and water levels are just right, a “moonbow” will appear like magic. The mist rising from the falls creates the rainbow-like phenomenon, the only one in the Western Hemisphere.

Located in Cumberland Falls State Resort Park, Cumberland Falls has a visitor’s center, a gift shop, restrooms, a snack bar, a big parking lot, and free admission. A walkway to see the falls is easy to maneuver from the parking lot. A more adventurous walk goes past that point to sites below the falls.

Exhibits inside the visitor’s center showcase the area’s geology, history, and Indigenous life. Two live critters attract attention in their private homes. One is a common musk turtle, or stinkpot turtle, which got its name due to its ability to release a foul musky odor from scent glands on the edge of its shell, probably to keep predators away. The other live critter is a diamondback water snake, a large nonvenomous snake that’s frequently mistaken for the venomous cottonmouth. The snake seemed to eye me as I quickly moved past.

Visitors can buy a bag of gemstones in the visitor’s center and see what treasures might be in the bag. A flume outside the center is where you can place the rough material in the bag onto a screen that’s provided. Wash and rinse the material with water from the flume. Never know what gems might be in the material — quartz, ruby, moonstone, topaz, amethyst, garnet, sapphire, emerald, and much more. It’s a fun activity for children and families.

Cumberland Falls: 7351 Highway 90, Corbin, KY 40701

Where to eat and drink in Corbin

Wrigley Taproom & Eatery

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As soon as I saw the old brick wall, I knew where The Wrigley Taproom & Eatery in downtown Corbin got its name. The historic mural depicts a small elfin character pointing to a pack of gum near the restaurant’s front window. The gum? Wrigley’s, of course, founded in 1891 in Chicago by William Wrigley Jr. My favorite gum as a child was Wrigley’s Juicy Fruit.

When restauranteur Kristin Smith saw the 1919 sign, she loved it so much that she named her new restaurant after it. Since 2014, hungry folks have found their way to The Wrigley Taproom & Eatery to enjoy the large selection of craft beer, creative cocktails, and fresh farm-to-fork food.

For dinner, I chose a tasty panko-crusted Springer Mountain chicken breast with mozzarella, house marinara, and Parmigiana Reggiano butter on a toasted brioche bun. I also couldn’t pass up the “big ass pretzel,” a huge salted pretzel with beer cheese and house-made mustard.

As I left, I stopped to read a sign over the restaurant door that describes the restaurant’s goal very well: “The Wrigley Taproom & Eatery strives to care for and nurture our community in mind, body, and spirit, one inspired plate at a time.”

Wrigley Taproom & Eatery: 207 S. Main St., Corbin, KY 40701

Where to stay in Corbin

Cumberland Falls State Resort Park

I’m seldom distracted from breakfast. But on this pre-dawn morning, I left my eggs, sausage, and fruit sitting on the Riverview Restaurant dining room table and headed outside. Cumberland Falls State Resort Park was treating us to a spectacular sunrise. Breakfast could wait.

When we arrived at Cumberland Falls State Park the night before, it was bedtime. I didn’t see much outside but enjoyed the lovely decor inside DuPont Lodge. The lodge features solid hemlock beams and knotty pine paneling, plus massive stone fireplaces and a large observation deck overlooking the Cumberland River meandering through the hillside. Lucky for us, autumn leaves were glorious the next morning, and many folks were taking photos on the DuPont Lodge observation deck.

The lodge has 51 rooms with great views. My room for the night had two full-size beds, lovely flower prints on the wall, two big windows, a TV, and a bathroom with a shower and tub. Be aware that DuPont Lodge and Riverview Restaurant closed on November 1, 2025, for renovations that are expected to take 18 months.

Cumberland Falls State Resort Park: 7351 Highway 90, Corbin, KY 40701

Pikeville

Things to do in Pikeville

Hatfield & McCoy Driving Tour

After an almost three-hour drive, we arrived in Pikeville (pop. 7,754), where we took a Hatfield-McCoy Driving Tour to learn more about the notorious feud. At the local visitor’s center, visitors can pick up a free driving tour brochure that features directions to each site as well as a CD or USB featuring narration and music.

In the beginning, Anderson “Devil Anse” Hatfield and Randolph “Randall” McCoy were friends. Hatfield lived on the West Virginia side of the Tug Fork of the Big Sandy River, which snaked along the boundary between Kentucky and West Virginia. McCoy lived on the Kentucky side of the river. What started the feud? Probably money, jealousy, and a desire for revenge fueled by the Civil War, the theft of a pig, family squabbles, killings, and a doomed love affair between Roseanna McCoy and Johnse Hatfield. It all seemed to culminate in a horrific massacre on New Year’s 1888.

We stopped at an old-fashioned well at what was once Randall McCoy’s home where a bunch of drunken Hatfields decided they would end the feud once and for all. The Hatfield plan was to kill Randall McCoy and his family and burn down their cabin. Randall fled, escaping into the woods. His son Calvin and daughter Alifair were killed in the crossfire. His wife Sarah suffered a crushed skill after being badly beaten by the Hatfields.

Randall died a bitter man at age 88. His death was caused by accidentally falling into a cooking fire where he was badly burned. He lingered for three months before he died.

Devil Anse caught pneumonia and died in his sleep, also at age 88. Before his death, Anse found religion and was baptized in a nearby creek. Tales are that the water in the creek boiled because Anse was so evil.

Pikeville-Pike County Tourism CVB: 685 Hambley Blvd., Pikeville, KY 41501

Where to eat and drink in Pikeville

Pauley Hollow Distillery

Part of the Hatfield-McCoy Feud Driving Tour is a stop at Pauley Hollow Distillery. Why? Besides being a great place for a cool bourbon drink, what does this distillery have to do with that historic feud?

Along with producing premium bourbon, apple brandy, rye whiskey, and much more, Pauley Hollow Distillery also creates a drink named “Fuel of the Feud.” The moonshine is produced using water taken from the Randall McCoy Well at the old homestead where much of Randall’s family was wiped out in a Hatfield massacre.

The idea for Fuel of the Feud was envisioned by Bob Scott, a Hatfield descendant who now owns the property where the McCoy cabin was burned. Made with West Virginia corn and Kentucky rye plus barley, the moonshine is 100 proof. A taste sure can open your eyes.

Founded in 2015, Pauley Hollow Distillery is the first legal distillery in Pike County. It’s owned by husband-and-wife team Jessica and Josh Martin. Jessica made one of the best Old-Fashioned cocktails I’ve ever enjoyed. She used Robert’s Reserve Kentucky Straight Bourbon Whiskey, a very small batch four-grain whiskey produced by Pauley Hollow Distillery.

Pauley Hollow Distillery: 91 Kate Camp Branch, Forest Hills, KY 41527

Chirico’s Ristorante

Chirico’s sure doesn’t look like a restaurant. It looks more like a beautiful historic home, which is exactly what it is — with an excellent Italian restaurant inside.

After the Hatfields burned the McCoy cabin on January 1, 1888, Randall and Sarah McCoy never returned to their Blackberry Creek property. Governors of both Kentucky and West Virginia urged the Hatfields and McCoys to move away from each other. The McCoys purchased this house near the riverbank on East Main Street in Pikeville, and Randall operated a ferry across the Big Sandy River.

Restauranteur Frank Ray Chirico dreamed of establishing an Italian restaurant in 1981. His idea was to use old family recipes that he passed along to his three sons. Originally the restaurant was located on Pike Street but moved to the former McCoy home on Main Street in 2008.

Judging from my lunch special, the family recipes are perfection. My large serving of pizza baked spaghetti and fettuccine alfredo was a very pleasing combination. It came with a side salad with ranch dressing and house garlic bread sticks. I also had a bottle of Ale-8-One, which sounds like alcohol but is really a soft drink. I’d learn more about Kentucky’s iconic soft drink when we visited our last small town.

Chirico’s Ristorante: 235 Main St., Pikeville, KY 41501

Pearse’s Place

After a long day of driving and touring, it was nice to cozy up to a table at Pearse’s Place at Dueling Barrels Brewery and Distillery, order a cold beer, and eat a grilled cheese sandwich and a monster pretzel with beer cheese. Since this is Pikeville, you can probably guess what the distillery name is referencing. Yep, the notorious Hatfields and McCoys. Hence, dueling barrels.

Eastern Kentucky’s first combined beer, bourbon, and moonshine operation, Dueling Barrels Brewery and Distillery opened in 2018 by founders Dr. Pearse and Deidre Lyons. An upstairs bar is named Pearse’s Place in honor of the late scientist and Irish entrepreneur.

Pearse’s Place: 224 Second St., Pikeville, KY 41501

Where to stay in Pikeville

Hampton Inn

Sometimes it’s nice to check into a chain hotel that you know will be modern, quiet, and comfortable. That’s the Hampton Inn in the heart of downtown Pikeville. My large room had a queen-size bed, microwave, mini-fridge, 50-inch HDTV, work area, and ergonomic seating. The hotel also features an indoor heated pool, fitness center, business center, and free WiFi.

But you know what I did? Got in bed and went to sleep. The day had been long and filled with fascinating stories and stops, but I was ready to rest. The next morning, it was breakfast at 7 AM and departure at 8 AM for the final small town on my itinerary.

Hampton Inn: 831 Hambley Blvd., Pikeville, KY 41501

Winchester

Things to do in Winchester

Creative Coffees Roastery

After a two-hour drive from Pikeville, it was great to stretch our legs and smell the fresh-roasted coffee at Creative Coffees Roastery in Winchester (pop. 19,254). Opened in 2009, Creative Coffees was founded by Debbie Hohman to help school groups and nonprofits raise funds for many different causes by selling special coffee. Creative Coffees also provides coffee service to restaurants, businesses, churches, and other folks who appreciate a tasty brew.

Debbie’s husband Jeff Hohman is one of Creative Coffees’ master roasters. The company uses the highest quality Arabica beans from Central and South American countries. Creative Coffees offers free tours and tastings.

Creative Coffees Roastery: 215 E. Broadway St., Winchester, KY 40391

Ale-8-One Bottling Co.

A successful businessman, George Lee Wainscott was fascinated when he first saw a carbonation machine. Why not create his own soft drink company, he thought? That’s what he did in 1902, operating out of a building in Winchester. Developing his own soft drink formula, Wainscott named his first cola product Roxa-Kola in 1906 after his wife, Roxanne.

But the nation’s largest cola company, Coca-Cola, filed a lawsuit against Wainscott and other independent cola makers. Wainscott won the lawsuit and also an appeal. However, he decided to create another recipe and drop the Kola name. The result was a combination of ginger with citrus.

What to name his new product? Wainscott was smart. He held a contest at the 1926 Clark County Fair to choose a name. The winner? A young fairgoer suggested the new soft drink be named after what it was — the latest thing. At the time, slang for the latest thing was “a late one.” Wainscott shortened that to Ale-8-One.

Other Ale-8-One flavors are cherry and orange cream. The drink also comes in zero sugar and caffeine free. Free factory tours are offered which include Ale-8-One samples.

Ale-8-One Bottling Company: 25 Carol Road, Winchester, KY 40391

Bluegrass Heritage Museum

The beautiful 1895 Victorian-era home of Dr. John Ishmael, which later served as a hospital, is now a museum. The Bluegrass Heritage Museum opened on October 12, 2004, and is filled with three floors of galleries dedicated to preserving the interesting history of Clark County. Each gallery concentrates on different aspects of history such as the Civil War, agriculture, telephones, barber shops, quilts, military history, slavery, and much more.

In 1927, Dr. E. P. Guerrant bought the private home and converted it into a hospital: the Guerrant Mission Clinic and Hospital. The hospital closed in 1971, but the first floor remained open as a clinic until 1989.

In the Guerrant Clinic and Hospital Rooms galleries on the museum’s third floor, you can see the operating room, scrub room where doctors and nurses prepped for surgery and cleanup, patient room, and more. Displayed on a wall is a bill for child delivery in 1947 — $141.35 for the operating room, medications, infant care, and a 10-day hospital stay.

My favorite gallery was Homer Ledford’s Workshop, which celebrates the artistry of the bluegrass musician and master instrument maker. He taught woodworking at the local high school until 1963 and was the inventor of the dulcitar (a combination of the dulcimer and the guitar) and also a maker of dulcijos (a combination of the dulcimer and the banjo) and dulcibros (a combination of the dulcimer and the dobro).

During his lifetime, Ledford made 6,014 dulcimers, 475 banjos, 27 mandolins, 26 guitars, 18 ukuleles, 13 dulcitars, three dulcijos, three dulcibros, four violins, and one bowed dulcimer.

Three of his instruments are in the Smithsonian Institute in Washington, DC: an Appalachian dulcimer, a dulcitar, and a fretless banjo.

Bluegrass Heritage Museum: 217 S. Main St., Winchester, KY 40391

Leeds Center for the Arts

One of Winchester’s first movie houses, the Leeds Theater has been an important part of the community since 1925. The name came from rearranging the letters of the owner, S.D. Lee. When the theater closed in 1986, the Winchester Council for the Arts restored it to its original appearance and reopened it in 1990 as the Leeds Center for the Arts.

A community gathering place, the theater features theatrical performances, concerts, art galleries, and educational programs. It also emphasizes providing a safe space where children can “learn to lead, discover their voice, and are valued for their uniqueness” through the education programs.

Leeds Center for the Arts: 37 N. Main St, Winchester, KY 40391

Where to eat and drink in Winchester

Smokin’ Howard’s Sports Bar & Grill

The smoker on the sidewalk in front of this cafe is a definite giveaway. Smokin’ Howard’s Sports Bar & Grill serves some mighty delicious Southern comfort food and scrumptious barbecue made from Paul Howard’s family recipes. It also had my favorite beer cheese. After all, we are in Winchester, said to be the birthplace of that tangy cheese dip.

The story goes that in the 1930s, cousins Joe and Johnnie Allman were looking for a complimentary concoction that would make customers at the Driftwood Inn on the Kentucky River in Winchester thirsty enough to buy more drinks. The result was a spicy beer cheese dip served with saltines and veggies. The dip drew many followers and, of course, increased drink sales.

Today, Winchester has a Beer Cheese Trail along with a Beer Cheese Festival, held the second Saturday of each June in historic downtown Winchester. Beer cheese fans can get a Beer Cheese Trail Digital Passport delivered via text or email that showcases 15 beer cheese stops in Winchester. The more stops you make on the trail, the more freebies you earn.

My lunch choice at Smokin’ Howard’s was a pulled pork sandwich with onion rings and greens. All of it was great, but I could have made a meal out of those greens and beer cheese.

Smokin’ Howard’s Sports Bar & Grill: 20 N. Main St., Winchester, KY 40391

Loma’s at the Opera House

For our last evening on the trip, we dined at Loma’s at the Opera House. Built in the late 1800s, the building was originally a cultural center for the area and later a sewing factory. Major renovations turned it into Loma’s fine restaurant in 2003.

A classy and comfortable restaurant, Loma’s has a great menu including beer cheese grits topped with garlic butter, sautéed shrimp, cherry tomatoes, roasted corn, candied bacon, and scallions. Loma’s is one of the stops on the Beer Cheese Trail. Someday, I hope to return and check off the rest of those great beer cheese places.

Loma’s at the Opera House: 103 S. Main St., Winchester, KY 40391

When to visit small cities in Kentucky and how to get around

Autumn is an ideal time to visit these small cities in Kentucky. The leaves are so colorful, and the temperatures are not too hot or too cold. Summer travelers are gone, so most attractions are not packed.

I flew into Blue Grass Airport (LEX) in Lexington, Kentucky. I flew American Airlines, which has the largest presence at the airport with around half of the airport’s flights. The airport is easy to maneuver and staffed with friendly folks.

To travel to all the cities on my itinerary, I rode in a shuttle with a driver. It would be best to drive your own vehicle or rent one at the airport because this itinerary does travel quite a bit of miles.