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Kentucky is a collection of charming small towns each with its own quirky sites, history, natural wonders, amazing food and, of course, bourbon. Here, TravelingMom Publisher and Kentucky native Kim Orlando, along with some of her friends, share where to go and what to do on a small town getaway for a weekend or family vacation. Tiny house houseboat rentals, broom-making and bourbon tastings are just a sampling of what you can expect from exploring Kentucky Wildlands and small towns.
Just about every destination in Kentucky is a short road trip away. It takes only 3.5 hours to drive from Newport, the northernmost point along the Ohio River, to Scottsville in the south, along the Tennessee state line. Kentucky road trips always take me longer, though, because I love to stop at the charming small towns and quirky oddities along the way.
For families looking for a weekend getaway or a history lesson, the Bluegrass State offers rich Civil War history and natural wonders in just about every small town. Even better for families, Kentucky is a super affordable vacation destination with lots of free things to do in Kentucky with kids all across the state.
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Kentucky Wildlands, a 14,000-square-mile region that is home to one of the most diverse ecosystems on the planet, also is home to some of the state’s cutest small towns, each with its own unique gem worth visiting.
My list below is a combination of my personal experience and the tips from my trusted friends who live there. It’s arranged in alphabetical order because it’s hard to say one Kentucky town is better than the next.
I would name Bardstown the most beautiful small town in Kentucky. Quaint and only 45 minutes south of Louisville, it is the bourbon capital of the world with shops and restaurants surrounding the town square.
My favorite things to do in Bardstown:
- Catch The Stephen Foster Story at My Old Kentucky Home State Park. The show, which has been running since 1959, features more than 50 Foster compositions, including “Oh! Susanna,” “Camptown Races” and, of course, Kentucky’s state song “My Old Kentucky Home.”
- Have a chocolate soda and a Johnny Boy (a chicken salad/BLT sandwich) at Hurst Discount Drug Store on Main Street. Ordering and eating at the old fashioned soda fountain counter is part of the fun.
- Visit Dave at The Blind Pig to learn about which bourbon distilleries to visit in the area.
- Head to Mammy’s Kitchen, where “country cookin’ makes you good lookin'” for homestyle country cooking and the best pie everrrr.
Stimulate your crafty side and overall creativity in one of the best small towns in Kentucky for art, crafts and art galleries. Berea’s LearnShops offers a range of classes aimed at both budding and experienced artists, from watercolors to fairy house construction.
Visit Berea College, the first integrated, co-ed college in the South. It has not charged students tuition since 1892. Instead, the liberal arts school operates a “work study program on steroids.” You can see the no-tuition promise at work. Literally. Berea College staff and students oversee 9,000 acres of land and reservoirs that provide Berea’s drinking water.
Don’t miss a chance to dine on organic farm to table foods at The Berea College Farm Store.
One of the fastest growing towns in Kentucky, Bowling Green is the biggest town close to Mammoth Cave. But hiking the underground caves at the national park is just one of the fun things to do in Bowling Green. Other favorites include:
- The Corvette Museum, which is just down the road from the manufacturing plant where “America’s sportscar” is made. There is a KidsZone with interactive activities where kids can design their own cars.
- Hiking at Lost River Cave. Or, if you prefer to ride, take the Lost River Cave boat tour.
- Touring the Historic Railpark & Train Museum. It features five fully restored historic railcars – a post office car, Duncan Hines dining car, high-class and low-class sleeping cars and the railroad president’s private car.
- Visiting Chaney’s Dairy Barn to see the Laley Astronaut Robotic Milker milk a cow.
- Hot Rods minor league baseball team and football and basketball at Western Kentucky University are big deals here.
- During the winter months, there’s ice skating downtown and every November, Gypsy Moon Marketplace transforms a horse stable into a bazaar for handmade and vintage goods.
Foodie Finds in Bowling Green
Georgia D., a student at Western Kentucky University, recommends these restaurants in Bowling Green:
- Spencers. This is my go-to place with my parents when they’re in town. I love the iced mocha and chicken salad sandwich. I take my mom there every time she visits.
- Griffs is an amazing local deli. Order the incredible giant baked potatoes. These spuds are piled with just about anything you can think of, although I’m a simple gal, so I usually just go with some cheese, bacon, sour cream and butter.
- Mariah’s is an upscale restaurant that my parents take me to when they visit. My go to on the menu is the Kentucky hot brown — an open-faced sandwich of turkey, ham and bacon, covered in creamy Mornay sauce and baked or broiled until the bread is crisp and the sauce begins to brown (all visitors must try this!). Plus, the dinner rolls at Mariah’s are the best in town!
- Food truck festivals are a “thing” in Bowling Green. Hundreds of people show up every time. The weirdest food truck for me is the Groovy Gus Donut Bus — expect some really good mini donuts with crazy toppings like fruity pebbles.
Campbellsville / Green River
My family is from Campbellsville so I return often. One of the best memories I have of living in Kentucky is lake life. Camping, pontoon rentals and hiking are available at Green River State Park and Green River Lake Marina just outside Campbellsville.
Campbellsville is located in the center of the state, about a 2-hour drive to the Kentucky border in any direction.
The things I love to do in Campbellsville are:
- Follow the self-guided Tebbs Bend Civil War Battle tour (listed in the National Register of Historic Places). The 3 mile self-drive tour off Hwy 55 commemorates a bloody and important battle that Confederate General John Hunt Morgan was confident he would win against an untried and much smaller group of Union soldiers from Michigan. Even though Morgan’s regiment outnumbered the Union soldiers 10 to 1, he lost the battle after a very intense four hours.
- Walk the path at Trace Pittman Greenway, a lovely paved 3-mile loop along Trace Creek, just outside of downtown.
- Order a green smoothie at Sonshine Natural Foods
Probably best known for the Harland Café, where Colonel Harland Sanders created the recipe for Kentucky Fried Chicken. Listed on the National Register of Historic Places, it is now a museum with photos and information about the original KFC and its founder.
My cousin did her medical school residency in Corbin, KY and she recommended we stop at one of her favorites, The Root Beer Stand. It’s an old school drive up (not drive thru) where waitresses come to your car to take your order. A large root beer float tastes amazing and will set you back $3.
Austin City Saloon, downtown, offers atmosphere, live music on weekends, a rooftop patio and good food. The burger menu is solid and the bourbon menu was interesting but it was the Fries in Low Places that caught my attention. A must try!
Cumberland Falls State Resort Park
OK, this isn’t technically a small town in Kentucky. But it is a must-visit spot. Woods surround the resort at Cumberland Falls and the hike to the falls easy access. Sheltowee Trace Resort is just 5 miles from the Falls and has all kinds of fun kid activities from zip lining to glamping in a covered wagon.
My husband prefers indoor plumbing so we stayed in one of the cabins in a more secluded part of the property. The cabin was new, cozy and the first ric of firewood is free. Adventurous activities like kayaking, tubing and a river boat cruise can all be organized by Sheltowee Trace.
TravelingMom Tip: You will NOT see the waterfall on the cruise; it is a one hour tour of the river. But if you book a nighttime moonbow cruise, you can see the rainbow colors from the waterfall spray illuminated by the moon. (Be sure to check dates and weather ahead of time to ensure the moon will be shining the night you want to visit!) Also, skip the snack bar aboard, (limited options and pricey) but do load up on s’mores bling in the cute shop.
One of the most beautiful small towns in Kentucky, Danville is the place to experience Civil War history, Kentucky-style. My friend Bruce, a Harrodsburg native, says this about Danville:
Experience the authenticity of one of the most unaltered battlefields of the Civil War at the Perryville Battlefield State Park. Watch reenactors recreate the intensity of a Civil War battle at the 160th anniversary celebration in 2022.
There is a lot of bourbon to taste in Kentucky. Locally owned Wilderness Trail Distillery is at the top of my list. Relatively young, it is already the 17th largest distillery in the US, distilling bourbon whiskey, rye whiskey and Blue Heron vodka. It is special because the guides demonstrate all phases of distilling and have great technical knowledge of bourbon. Plus, the Rye whiskey is outstanding.
Fun things to do in Danville, one of the most beautiful Kentucky towns, include:
- Follow Danville’s Centre College self-driving tour to see the African-American Forgotten Landmarks.
- Eat at Copper and Oak (everything on the menu is great).
- Visit Abraham Lincoln’s grandmother’s cabin.
- Bring your doll to the Great American Dollhouse Museum.
- Drive the Hemp Highway.
Sisters Amy and Mary, both Glasgow residents, recommend visitors take in a show at The Historic Plaza Theater. It has hosted big names like The Kentucky Headhunters, Black Stone Cherry and Marty Stuart. It’s also home to a local theatre group, the Far Off Broadway Players, that does a great job with kid-friendly shows as well as “The Legend of Sleepy Hollow,” “Arsenic and Old Lace,” “It’s a Wonderful Life” and “To Kill a Mockingbird.”
Check this website for events like the guided cemetery tour, quilt show and local artists’ showcases, offered throughout the year.
Glasgow is another foodie spot, starting with the wonderful homemade cheese at Kenny’s Farmhouse Cheese, located out in the county. The cheese is known all over Kentucky and beyond.
Other foodie stops the sisters recommend are:
Little Taste of Texas. Best salad dressings EVER – all homemade. It’s also known for high quality meat.
The Fine Arts Bistro for Saturday brunch. Don’t leave without a biscuit – these are top-rated in our family. Then head over to The South Central Kentucky Cultural Center where you can take a walk through time to see the country store display with original items and furnishings.
The Farmer’s Market, open every Saturday morning on the square in Glasgow. Shop local handmade soaps, wines, crafts, jams and homegrown fruits and vegetables. Grab a coffee at King’s Cafe and visit a few stores like Carsen & Shae for some cool & funky vintage items.
Harrodsburg resident Bruce says the following about his hometown:
Shaker Village is a restored Shaker Community dating back to the early 1800s. Situated on more than 3,000 acres of natural beauty and 40+ miles of trails, there are plenty of unplugged activities to explore. Expect to see live demonstrations of broom making, rug hooking and spinning at The Historic Centre, The Farm and The Preserve. Cruise the Kentucky River. Try horseback riding. Stay at The INN and eat true farm-to-table food (that you or your kids may have picked!) at The Trustee’s Table in the main building.
Fort Harrod State Park is the oldest permanent settlement east of the Allegheny Mountains. It is a full-size replica of the fort that was originally constructed in 1774, replete with handmade utensils and tools pioneers used in everyday life. Visit Pioneer Cemetery, the oldest cemetery in Kentucky and the Lincoln marriage temple – the cabin where Abe Lincoln’s parents were married in the State Park.
A popular place to kick off a tour of the Kentucky Bourbon Trail, the Beaumont Inn is a historic Bed and Breakfast, that has been in business since 1919. The restaurant, serving family heirloom recipes, won a prestigious James Beard Award in 2015. Try an Old Fashioned at the Old Owl Tavern, one of the Top 10 bourbon bars in Kentucky.
Lake Cumberland and Lake Cumberland State Park
Houseboats on Lake Cumberland. Photo credit: Kim OrlandoExpansive, deep and beautiful, Lake Cumberland is surrounded by 1,200+ miles of shoreline (more than Florida!) including a few state parks, boasts 101 miles of water and several marinas for boat rentals.
Lake Cumberland State Park is one of several state parks on the lake and offers several lodging options: Lure Lodge, 3 types of cabin rentals, and campsites, including accessible sites.
The rooms at Lure Lodge are comfortable and many have balconies, with beautiful views of the woods. It is family-friendly with an indoor pool, game room and nearby restaurant overlooking the lake. For more space, there are several cabin options near the lodge. Camping is popular at the state park and 6 handicap-accessible sites were added in 2021.
Although Lake Cumberland State Dock is in the state park, it is privately owned. The State Dock is the largest marina on the lake and has more houseboats available to rent in one location than any other marina in the US. Boat rentals range from fishing boats to 10 cabin houseboats that sleep 22 guests. Skip the massive Airbnb rentals for the next family reunion! Pile everyone into a houseboat and hang out on the lake.
Nervous about docking a houseboat? Don’t be. Lake Cumberland State Dock removes the biggest barrier to renting: lack of houseboating experience. Someone will drive the houseboat out to the lake and/or pull it in for you. I love that this service is a standard offer, not a special request. There is even pizza delivery available to the boat.
There are plenty of good reasons to hang out at the dock – a fun atmosphere with a store packed with Huk fishing gear and Lake Cumberland souvenirs, delicious fried catfish and lake-friendly cocktails at the Boat Yard Bar & Grill. I recommend the catfish and giving the peanut butter pie a try.
In Kentucky, we pronounce this town name “Lebnin.” Its trails lead to quilts and bourbon as well as trees and streams. The Marion County Trail features Limestone Branch (a favorite distilling tour of mine) where Steve Beam, artistic horticulturalist and descendant of Jim Beam, distills a fantastic botanical gin and a large selection of bourbons and whiskeys. His gardens are spectacular.
Gigantic murals of quilts decorate the sides of barns along the Quilt Trail which covers three states. You can hike the Fagan Branch Trail and fishing is available at Fagan Branch Lake, Marion County Lake and Rolling Fork River.
At Kentucky Cooperage, white oak barrels are constructed, charred and shipped around the world. Various levels of char are available and the demonstrations are fascinating.
Tour the Loretto Motherhouse where the Sisters of Loretto maintain a 200-year Heritage Center chronicling peace and justice activism. A little further down the road in Loretto, visit Maker’s Mark, a world renowned bourbon distillery that has been operating since 1953.
While I’ve visited Midway (my “sammich” recommendation is below), my friend Bob lives there. Here’s what he has to say about it:
My hometown of Midway has more than one hat. Its population and year of incorporation are about the same number—1830—yet Midway’s birth is unique: It’s the only town in Kentucky founded by a railroad company. Situated midway on a line between the city of Lexington and the state capital, Frankfort, Midway still has a railroad running through the middle of its downtown.
Alas, you cannot ride the rails yourself; passenger service ended in the 1960s. Still, it’s quite an event when a freight train rumbles through town. Every visitor stops what they’re doing—kids and adults alike—to watch the train. And on a magical morning every December, when the train stops and Santa Claus emerges from the caboose, he’s greeted by hundreds of holiday-happy folks.
This small town in Kentucky is a great foodie stop. Locally-owned shops and restaurants line both sides of the train tracks. People drive from all directions to feast on everything from fine dining and upscale Mexican fare to pizza and pub grub. Here are some personal favorites for families:
The Goose & Gander: With a menu that varies from salads to gourmet burgers, pizza and fried chicken dinner, “The Goose” also offers excellent trackside seating options: Dine inside close to the fireplace when it’s cold, but when weather allows, the shaded patio is the best in town.
Don Jockey: The newest restaurant on Railroad Street, Don Jockey serves up authentic Mexican cuisine. Favorite dish: Quesadillas Jalisco.
Wallace Station Deli: Situated amid horse farms in a former country store four minutes from Railroad Street, this superior sandwich shop was featured on Diners, Drive-Ins and Dives, Guy Fieri’s Food Network Show. Bob’s favorite sammich: thin-sliced country ham and pimiento cheese on house-made bread. My favorite: the Cubano – pulled pork, swiss, pickles on rye; My kids say the burger is the best they’ve tasted.
Head here in the fall to pick from 25 varieties of apples and other fruits at Haney’s Appledale Farm. To me, the highlight is eating one (or maybe more) of the famous one-of-a-kind family-recipe fried apple pies. They taste just like the ones my Mema made.
Lee’s Ford Marina, a privately owned full service marina on Lake Cumberland, is 4 miles outside of Somerset in Nancy, KY. The marina offers music, boat rentals, food and even Sunday church service. The owner, JD Hamilton, is especially proud of his creation: the tinyhouse houseboat – he has at least 8. He built a tiny house on a pontoon platform, which makes it more affordable without giving up any creature comforts on the lake. I toured the tiny-house houseboat and was impressed by the size of the rooms and the slide off the back of the boat. Next time I hope to take one out on the water. I was assured that if I needed help docking, all I had to do was ask.
Learn about the Union victory at Mill Springs (aka Nancy) at the Mill Springs Battlefield Museum and Visitors Center.
Once a small town, Shelbyville Kentucky has grown into a bustling city. Only 15 miles from downtown Louisville, Shelbyville is especially enjoyable in the fall and winter, says my friend Melissa, a Shelbyville resident. She recommends visiting:
Gallerin Farms. Gallerin Farms is open seasonally and offers a variety of family fun activities. A greenhouse full of brightly colored perennials and annuals will greet you in the spring and summer (along with strawberry picking). The farm really shines in the autumn months when it offers U-pick pumpkins, hayrides and loads of fun fall festivities. Gallerin Farms is open from April 1-October 31 each year.
Wakefield-Scearce Galleries. Once an all-girls boarding school, Wakefield-Scearce offers some of the best antique shopping in Kentucky. It sells furniture, silver (yes, even Julep cups!) and home accessories. Each holiday season, the galleries are decked out with gorgeous Christmas trees and decorations. Stop by the restaurant, the Science Hill Inn for my favorite, shrimp and grits, made with grits from Weisenberger Mill in Midway. My kids even took a package of the grits with them when they left for college.
A Distillery. Shelbyville features two distilleries that are worth a stop: Jeptha Creed Distillery offers tastings, tours and the Creed Cafe, which is a great place to grab lunch or a quick bite. Also in Shelbyville is the Bulleit Distilling Co. Visitor Experience, which includes distillery tours, tastings and special events throughout the year.
Somerset is on the northeastern side of Lake Cumberland, near Daniel Boone National Forest, with miles of trails, an abundant outdoor life, growing downtown and bourbon scene.
More things to do in Somerset:
- Creep around the International Paranormal Museum and Research Center.
- Stop in at The Mole Hole downtown, a unique gift shop and bar, for some secret recipe chicken salad and Tammy’s crazy good lemon drop.
- Plan a weekend in July around the Master Musicians Festival, which caters to the whole family.
- Catch on the patriotic story of Horse Soldier, the new bourbon coming to town, started by a team of veteran Green Berets as a true recovery mission.
The coal mine in Stearns closed in 1942, but you can still ride the train and visit the mine with one of the miners’ descendants. Rob grew up there and provides a vivid image of coal mining life on his tour of the replica of the original town where his grandfather worked.
Authenticity is important and it is evident in the care taken with the details. Reproductions of the barber shop, doctor’s office and one-room school house/church give visitors a glimpse of what life was like for the miners and their families.
Upgrade the authenticity with a stay on property in a tract house overlooking the train and school house.
Just a few miles north of the Tennessee border, and 5 minutes from the Big South Fork Railway in Stearns, KY, this town of 1,100 people is worth the 30 minute detour off 75 for a visit to The Dairy Bar. It’s 1950’s style theme includes the option of dining in or in your car. This is where my Italian husband tried fried a bologna sandwich for the first time, made by professionals. I also had a couple of firsts – my first corn nugget (tasty but no need to eat that again), and pie in a cup- the ice cream version of coconut pie. Friendly staff, very affordable and absolutely delicious.