A trip to Kentucky’s beautiful Appalachian region should be on everyone’s bucket list for its stunning scenery, unique culture and fascinating history. 

 

Southeastern Kentucky is a fantastic choice for those who love exploring small cities across the U.S. The Blue Grass Airport (LEX) in Lexington is a convenient option for travelers flying into the region. These small cities are within easy driving distance of one another, making them perfect for a vacation that will satisfy all kinds of travelers.

Here are 5 charming small cities in Kentucky that show why the Bluegrass State is worth a visit.

1. Berea

Located just a 45-minute drive south from the Blue Grass Airport, Berea is a wonderful destination for those looking to experience the artistic traditions of Kentucky’s Appalachian region. Along the scenic route, travelers are treated to picturesque views of rolling horse farms and the lush, green landscapes that make this area so iconic. 

A Historic Hotel With a Heart

Plan your stay at the Historic Boone Tavern Hotel, built in 1909 and named after the legendary Appalachian figure Daniel Boone. This elegant hotel features 63 rooms and is owned and operated by Berea College. The college provides tuition-free education to low-income students through a unique labor program, where students work on campus, including at the hotel, gaining invaluable skills while supporting their education.

The Boone Tavern Restaurant offers a refined dining experience with a menu rooted in regional traditions. Start your meal with the Spoonbread Service, a rich, buttery bread with a custard-like texture, beloved by locals and celebrated annually at Berea’s Spoonbread Festival. The hotel’s longtime signature dish is Chicken “Flakes,” featuring shredded, poached chicken in a creamy sauce, served within a crisp, handcrafted potato nest. Stop by for breakfast, where hearty southern comfort dishes and lighter options like Chia Pudding are served. For coffee, go to the Frost Cafe, conveniently located inside the hotel.

Adjacent to the hotel is Berea College, a trailblazing liberal arts institution that has championed equality and education since its founding in 1855, becoming the first integrated college in the South. The hotel’s rooms feature wooden furnishings crafted by Berea College students, showcasing their exceptional craftsmanship. Students’ contributions to the college and the hotel highlight the community’s commitment to education, hospitality and tradition.

Folk Arts and Crafts Capital

Known as the Folk Arts and Crafts Capital of Kentucky, Berea is a haven for art lovers. The city’s annual Berea Craft Festival draws over 100 artisans from across the country, offering impressive live demonstrations in pottery, fiber arts, blacksmithing and loom weaving. Public art is displayed throughout Berea, with murals and sculptures in College Square. Visitors can admire these beautiful works of art with a self-guided walk.

Through its LearnShops programs, visitors can immerse themselves in Berea’s creative spirit with hands-on workshops led by master craftspeople. Open to all ages, these sessions explore skills like blacksmithing, woodworking and fiber arts.

Take a Hike

Berea, Kentucky, offers over 19 miles of trails, with the Pinnacles in Berea College Forest standing out as a premier destination. Recognized by Outside magazine as Kentucky’s top hike, the Pinnacles provide stunning vistas, convenient access to Daniel Boone National Forest and close proximity to nearby attractions.

The Pinnacles are sandstone outcroppings within Kentucky’s Knobs region. This area forms a horseshoe around the lower-lying Bluegrass Region, with the more erosion-resistant sandstone contrasting with the neighboring limestone. The hiking trails to the Pinnacles are located within Berea College Forest, owned and managed by the college’s forestry department.

 

2. Stearns

After soaking in Berea’s artistic charm, head 50 miles southwest to Stearns, a hidden gem in McCreary County. The drive offers a chance to witness the changing landscapes of Kentucky’s Appalachian region. As you leave Berea’s bustling arts scene behind, you’ll be immersed in the area’s natural beauty, with dense forests and scenic hills welcoming you to Stearns.

Hop Aboard a Historic Railway

McCreary County is nestled within 640,000 acres of lush timberland, making it a haven for nature lovers. One of the best ways to experience this natural beauty is aboard the Big South Fork Scenic Railway. The 3-hour round trip includes a 45-minute scenic ride to the historic Blue Heron mining community, where you’ll spend 1.5 hours exploring its fascinating outdoor museum. The journey concludes with a 45-minute return trip, providing ample time to take in the picturesque views of the forested landscape. Fall is ideal for this experience, as the colorful foliage enhances the stunning backdrop. 

Explore an Abandoned Mining Community

Blue Heron, once known as Mine 18, is an abandoned coal mining town that was operated under Stearns Coal and Lumber Company. The mines, active from 1937 until December 1962, were home to hundreds of workers and their families living in this remote community along the Big South Fork River until the mines became unprofitable.

At Blue Heron, visitors can wander through “ghost structures” that replicate the original buildings of the 1950s mining town. These structures offer a glimpse into life during the mining era, with exhibits, photographs, artifacts, and audio stories shared by former residents. Life was difficult and isolating for these people, and the exhibits poignantly convey these hardships. 

Dining at the Depot

After your train ride, head over to the Whistle Stop restaurant inside the depot. This veteran-owned eatery is known for its hearty American fare and welcoming atmosphere. Locals rave about the burgers, including the famous Triple Fried Burger and the Mushroom Swiss Burger. Don’t skip on the Fried Green Tomatoes, which are a crowd favorite.

If possible, grab a seat by the window to enjoy a scenic view of the train tracks while you dine. With a diverse menu and affordable prices, the Whistle Stop is the perfect spot to fuel up before or after your train adventure.

An Exciting New Train Experience

The Bluegrass Train Experience, a new tourism initiative, highlights Kentucky’s deep connection to railroading. This multi-county project includes Bowling Green, Bardstown, Oldham County, Woodford County, McCreary County, and Warren County, all with rich railroading histories. The program offers visitors 13 unique train experiences, including museum tours on wheels, scenic train rides through the countryside, and historic diner trains. It’s a chance to explore Kentucky’s spirit while celebrating trains’ vital role in shaping the state.

 

3. Corbin

Just a 45-minute drive south of Berea, Corbin is a charming town renowned as the birthplace of Kentucky Fried Chicken. Its quaint, walkable downtown is surrounded by natural beauty, offering visitors access to nature trails, white-water rafting, fishing, horseback riding and abundant wildlife, making it an ideal spot for outdoor enthusiasts.

A Fascinating State Park

Celebrate Kentucky State Parks’ 100th anniversary at Cumberland Falls State Resort Park. The resort is a fantastic destination, renowned for its breathtaking views and the iconic Cumberland Falls, also called the “Niagara Falls of the South.” The falls, standing 65 feet high and 125 feet wide, create a magical mist that forms a moonbow, an enchanting natural phenomenon visible only on clear nights during a full moon and the only occurrence in the Western Hemisphere.

Cumberland Falls State Resort Park offers abundant outdoor adventures, from hiking scenic trails like the Moonbow Trail to horseback riding through the stunning eastern Kentucky forest. The park also features gem mining, where visitors can search for colorful gemstones like amethyst, garnet, and quartz at the gemstone flume. For those interested in water activities, Sheltowee Trace Adventure Resort provides guided rafting trips on the Cumberland River, including a thrilling experience beneath the majestic Cumberland Falls.

A Cozy Lodge Surrounded by Beauty

After a day spent outdoors, retreat to the historic DuPont Lodge, a perfect blend of rustic charm and modern comfort. Renovated in 2006, the lodge features 51 rooms with massive stone fireplaces and a spacious observation deck offering breathtaking views of the Cumberland River and the Appalachian Mountains. Guests can enjoy meals at the Riverview Restaurant, which boasts stunning views through its vast windows. The lodge also offers an outdoor pool for a refreshing dip after a day of exploration. 

For those seeking a more secluded stay, Cumberland Falls State Resort Park offers 25 cozy cottages and cabins, each with full kitchens, private yards, and most featuring porches or patios. Located near the DuPont Lodge, these accommodations provide a peaceful retreat while still being close to the park’s many outdoor activities.

Exploring Downtown Corbin

Downtown Corbin offers a variety of charming attractions for all interests, starting with the Pinball Museum of Corbin. This unique museum features over 56 vintage pinball machines, offering endless entertainment for both kids and adults. With a single admission fee, visitors can enjoy a fun and nostalgic experience while learning about the history of pinball, with machines dating from 1969 to 2022. The museum also provides historical insights into the evolution of pinball, showcasing how the machines have changed over the years, both in design and functionality.

For music lovers, White Rabbit Records is a hidden gem. This small, locally-owned store features a curated selection of vintage vinyl, CDs and cassettes. Spend time flipping through the racks or chatting with the friendly staff about your favorite music.

Shopping in Corbin is also a delight. The Enchanted Boutique on Main offers a variety of charming jewelry, clothing, purses, and accessories, perfect for finding a special gift or treating yourself to something new. For a hands-on experience, head over to Campbell’s Ceramics, where you can paint your own ceramic masterpiece or join a guided class to learn new techniques.

When it’s time to unwind, The Wrigley Taproom & Eatery offers a fantastic place to relax. Known for its farm-fresh ingredients, a wide selection of craft beers, and over 60 Kentucky bourbons, it’s the perfect spot to enjoy great food in a welcoming atmosphere. Local favorites include the Brussel Sprouts and the Salmon BLT Taco, both brimming with flavor.. With features in publications like Time Magazine and Food & Wine, it’s no surprise that locals and visitors rave about this beloved eatery.

Colonel Sanders’ Indelible Mark on Corbin

A visit to Sanders Park in downtown Corbin offers a chance to celebrate the legacy of Colonel Harland Sanders, the town’s most famous resident and creator of Kentucky Fried Chicken. The park features a life-size bronze statue of the Colonel and memorial bricks and plaques that share his remarkable story. Explore the Secret Recipe garden, showcasing some of the herbs and spices used in his iconic chicken recipe, and enjoy the park’s status as an official monarch butterfly waystation. 

Sanders Cafè and Museum is just a short drive from downtown Corbin. This historic site is where Colonel Sanders first perfected his famous recipe. Visitors can tour the restored café, view memorabilia and learn more about the legacy of the world-famous brand.

 

4. Pikeville

Two hours northeast of Corbin lies Pikeville, the heart of Appalachia. Pikeville is also on the southern stretch of the Country Music Highway, a region that produced songwriters Dwight Yoakam and Patty Loveless. The rugged beauty of this small city is unparalleled, making it a great destination for those looking to explore the age-old traditions and landscapes of Eastern Kentucky. 

Where to Stay

For a comfortable stay, opt for the Hampton Inn, located in downtown Pikeville and steps away from the University of Pikeville campus, restaurants and shopping. The hotel rooms are spacious, clean and comfortable. Amenities include a free hot breakfast, a fitness center and an indoor pool.

The Hatfield and McCoy Saga

The infamous Hatfield and McCoy rivalry certainly comes to mind when one thinks of Pikeville. The feud, rooted in Civil War loyalties and a tragic love story, claimed over a dozen lives and symbolized family rivalry in American culture. After watching countless TV shows and reading literature on this historic feud, visitors can take the self-guided Hatfield-McCoy Feud Driving Tour.

A Feud Driving Tour brochure can be found at the Pikeville-Pike, KY Welcome Center. The brochure includes directions to each site and a CD or USB that features narration, music and historical markers highlighting key locations from the conflict.

The Hatfield McCoy historic sites are sectioned off into 3 main sections: 

• Pikeville City
• The Blackberry area of Pike County 
• Sarah Ann, West Virginia. 

Several key locations in Pikeville:

• The gravesite of the McCoy family, 
• The “Cotton Top” hanging site, 
• The Old Courthouse, where many of the feud participants were tried
• The Hatfield McCoy Museum. 

The tour in Pikeville typically takes about 45 minutes to two hours, while the entire tour can take approximately 4 to 6 hours.

The “Fuel of the Feud”

Visit Pauley Hollow Distillery as part of your Hatfield and McCoy tour. The distillery’s newest drink is Fuel of the Feud, made from the water drawn from the McCoy well. The well is located on the property where the Hatfields attacked the McCoy homeplace, on New Year’s Eve 1888, burning it to the ground. Bob Scott, a Hatfield descendant, now owns the property where the McCoy cabin was burned. 

Operating as the first legal distillery in Pike County, Pauley Hollow also offers premium bourbon, apple brandy, rye whiskey and much more. Founders Jessica and Josh Martin are a hard-working husband-and-wife team. Jessica does the bottling, and Josh does the distilling. Be sure to visit the Farmhouse Tasting Room to sample some of their products and indulge in craft cocktails. 

Pauley Hollow Distillery is just one stop along the newly launched Moonshine Trail. This trail of small distillers is located across Kentucky and shares the moonshine tradition with visitors from around the world. 

Where to Eat

Look no further than Chirico’s Ristorante for a delicious lunch or dinner. This historic structure was once the home of Randolph McCoy, the patriarch of the McCoy family. Owner and founder Frank Ray Chirico moved his restaurant to the former McCoy home in 2008. 

From his parents, Frank learned how to make sausage, perfect the dough-making process, and blend great sauces. He has passed his teachings of old-world Italian Cuisine on to his three sons. You can’t go wrong with anything on the menu, but calzones are a fan favorite.

Pearse’s Place at Dueling Barrels Brewery and Distillery is another fantastic eating spot in Pikeville. It serves local craft beer, award-winning small-batch bourbon whiskeys and signature cocktails. For starters, order a Bavarian Pretzel with delicious beer cheese. The Fried Green Tomato Grilled Cheese is everything you dreamed it would be. As you leave, take some photos of Umbrella Alley across the street. 

 

5. Winchester

From Pikeville, head westward for approximately 2 hours to Winchester. Known as the Beer Cheese Capital of the World and the birthplace of the iconic Ale-8-One soft drink, this charming city leaves a lasting impression on all who visit. Winchester is alive with culture and history, offering visitors various activities and experiences.

A Journey Back in Time

Celebrating its 20th anniversary, the Bluegrass Heritage Museum is a pleasant surprise to those who enter, offering a variety of displays that highlight different facets of Kentucky life. From the Eskippakithiki Indian Village to Daniel Boone’s settlement of Boonesboro, the museum offers a nuanced glimpse of Kentucky’s past. The most unique feature of the museum is a room on the third floor that displays remnants of the building’s former use as a medical clinic. Exhibits on local agriculture, military history and telephones provide an insightful experience for history enthusiasts and casual visitors alike.

Located in the heart of downtown Winchester, Leeds Center for the Arts has been a staple in the community for nearly 100 years. Originally a single-screen movie theater when it opened in 1925, it has since transformed into a lively arts venue offering a variety of performances, including live music, drama, and films. The theater hosts exciting events, with upcoming shows like Junie B. Jones The Musical JR and The Lightning Thief: The Percy Jackson Musical.

Downtown Adventures 

Downtown Winchester is a hub for art lovers, with several venues offering creative experiences. Arts On Main Gallery features a dynamic collection of visual art from local artists, including oil, acrylic, and watercolor paintings, prints, photography and more. Visitors can also purchase one-of-a-kind items like furniture and textiles. For those looking for more artistic treasures, Dirty South Pottery offers a distinctive stop with a wide range of handmade pottery, all crafted on-site. 

The Fly Witches offer a fun way to get fit with their Bungee Fitness classes. Guests enjoy training with the thrill of being suspended in the air by a bungee cord. This unique experience combines cardio and resistance training at a low-impact, high-intensity level and suits all fitness levels.

Behind the Scenes of Delicious Beverages

Discover the buzz around Ale-8-One, a beloved Winchester staple, at Ale-8-One Bottling Company. Founded and bottled in the city since 1926, this ginger and citrus-flavored soft drink has earned the title Kentucky’s Official Soft Drink. Known for its crisp taste and unique “kick,” Ale-8 rivals any big-brand ginger ale while maintaining a distinct local charm. Visitors can take free 30-45 minute factory tours to watch the bottling process and explore a cute gift shop filled with Ale-8 memorabilia. Best of all, guests can sample the iconic drink.

If you’re a coffee enthusiast, visiting Creative Coffees Roastery in Winchester is a must. Founded by Debbie Hohman in 2009, this locally owned business has roasted the highest quality Arabica beans from Central and South America. Creative Coffees partners with schools and nonprofits for fundraising through private-label products, providing opportunities to support local causes. Visitors can enjoy a tour of the roasting process and even sample coffee. Additionally, they sell tea, hot chocolate and coffee in single-serve pods. Debbie’s passion for quality and customer service shines through, making it a welcoming stop for all.

Savory Downtown Favorites

Known as The Birthplace of Beer Cheese, Winchester-Clark County hosts the Beer Cheese Trail, offering 15 stops where guests can savor this delicious, smooth spread made from cheddar cheese, beer, and spices. The annual Beer Cheese Festival, held every June, celebrates this local delicacy, bringing commercial and amateur makers together for a day of food and entertainment in historic downtown Winchester.

Head to Smokin’ Howard’s Sports Bar & Grill for hearty appetites. All the food is made from Paul Howard’s family recipes. Paul, a beloved figure in Winchester, serves up all your barbecue favorites, including Brisket Waffle Fries” and a Pork Tenderloin Dinner. Don’t pass up on the Beer Cheese Platter, a tasty beer cheese appetizer with crackers and vegetables. This downtown Winchester favorite with a smoker right out front is the ideal spot for foodies.

If you’re looking for an elevated dining experience, visit Loma’s at the Opera House, a historic building dating back to 1873. This restaurant offers a fresh take on comfort food with dishes like Loma’s Tots, Shrimp & Grits, and the signature Smoked Gouda Hot Brown, all made with seasonal ingredients. The ambiance of Loma’s is classy and elegant, a great choice for an evening of fine drinks and delicious food. Loma’s is also one of the stops on the Beer Cheese Trail. 

Start Planning Your Visit to Southeastern Kentucky

Kentucky’s Appalachian region is full of charm, character and surprises, but it’s the people who truly make this place special. As Maggy Monhallen, Park Manager of Cumberland Falls, puts it, “The Appalachian people have been through a lot, but they are resilient. They are the kindest people who will give you the shirts off their backs.” The warmth and hospitality of the people shine through.

The raw beauty and fascinating culture of these cities make for a meaningful vacation that you’ll remember for the rest of your life. Whether you’re exploring the natural wonders of Cumberland Falls, discovering local art in Berea or immersing yourself in the history of Winchester, every corner offers something new. The friendly locals are eager to share their stories, providing a personal connection to the area that adds to its allure. Start planning your trip to experience the heart and soul of this remarkable region.

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Cover photo courtesy Kentucky Tourism

Sara Aguinaga is a dedicated massage therapist and editorial contributor at Texas Lifestyle Magazine. She loves indulging in spa treatments, exploring diverse cuisines, and traveling. Follow her on Instagram @sweetsaraadventures